02-py-data-split-by-ligand-diversity.ipynb

{
 "cells": [
  {
   "cell_type": "code",
   "execution_count": 13,
   "id": "bf39dc6d-946e-479a-b292-77807d42b64b",
   "metadata": {},
   "outputs": [],
   "source": [
    "#!pip3 install numpy=1.20.2\n",
    "#!pip3 install pandas=1.2.4\n",
    "#!pip3 install pillow=8.1.2\n",
    "#!pip3 install scipy=1.6.3\n",
    "#!pip3 install rdkit=2022.3.4\n",
    "#!pip3 install scikit-learn=0.24.2\n",
    "#!pip3 install matplotlib=3.4.1\n",
    "#!pip3 install seaborn=0.11.1"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 12,
   "id": "fa9d1aa2",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "Name: rdkit\r\n",
      "Version: 2022.3.4\r\n",
      "Summary: A collection of chemoinformatics and machine-learning software written in C++ and Python\r\n",
      "Home-page: https://github.com/kuelumbus/rdkit-pypi\r\n",
      "Author: Christopher Kuenneth\r\n",
      "Author-email: chris@kuenneth.dev\r\n",
      "License: BSD-3-Clause\r\n",
      "Location: /opt/conda/lib/python3.8/site-packages\r\n",
      "Requires: Pillow, numpy\r\n",
      "Required-by: \r\n"
     ]
    }
   ],
   "source": [
    "!pip3 show rdkit"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 89,
   "id": "6156cf94-5b80-43e0-b360-ec2a28d427c0",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "Populating the interactive namespace from numpy and matplotlib\n",
      "2022.03.4\n"
     ]
    }
   ],
   "source": [
    "import pandas as pd\n",
    "import numpy as np\n",
    "import scipy\n",
    "from rdkit import Chem\n",
    "from rdkit import DataStructs\n",
    "from rdkit.Chem import Draw\n",
    "from rdkit.Chem.Draw import IPythonConsole\n",
    "from rdkit.Chem import rdDepictor, rdMolDescriptors\n",
    "from rdkit.SimDivFilters import rdSimDivPickers\n",
    "import time\n",
    "rdDepictor.SetPreferCoordGen(True)\n",
    "import rdkit\n",
    "%matplotlib inline\n",
    "%pylab inline\n",
    "print(rdkit.__version__)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 90,
   "id": "016fae1e-9600-4efe-a49d-23edebaaec6a",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_train_random_meta = pd.read_csv(\"work/training/dual-model/train-meta-random.csv\", sep=\",\", encoding=\"utf-8\")\n",
    "data_test_random_meta = pd.read_csv(\"work/training/dual-model/test-meta-random.csv\", sep=\",\", encoding=\"utf-8\")\n",
    "data_train_random = pd.read_csv(\"work/training/dual-model/train-random.csv\", sep=\",\", encoding=\"utf-8\")\n",
    "data_test_random = pd.read_csv(\"work/training/dual-model/test-random.csv\", sep=\",\", encoding=\"utf-8\")\n",
    "all_ligands = pd.read_csv(\"work/data/chembl_ligands_filtered_combined_tanimoto_smiles.tsv\", sep=\"\\t\", encoding=\"utf-8\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 91,
   "id": "a3c44182-cde2-4f69-b06f-59c34a62bfbc",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
       "      <th>chembl_id</th>\n",
       "      <th>tanimoto_index</th>\n",
       "      <th>smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>4twp</td>\n",
       "      <td>4twp_ligand_similar_196</td>\n",
       "      <td>CHEMBL3920052</td>\n",
       "      <td>0.844156</td>\n",
       "      <td>N(C(=O)c1c(cccc1)Sc1cc2c(cc1)c(n[nH]2)/C=C/c1c...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>4twp</td>\n",
       "      <td>4twp_ligand_similar_469</td>\n",
       "      <td>CHEMBL3967380</td>\n",
       "      <td>0.607143</td>\n",
       "      <td>c1cc(cc2c1c(n[nH]2)/C=C/c1ccccn1)Nc1ccccc1C(=O...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>4twp</td>\n",
       "      <td>4twp_ligand_similar_139</td>\n",
       "      <td>CHEMBL3948865</td>\n",
       "      <td>0.866667</td>\n",
       "      <td>c1(NC(=O)c2c(cccc2)Sc2cc3c(cc2)c(n[nH]3)/C=C/c...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>4twp</td>\n",
       "      <td>2v7a_ligand_similar_287</td>\n",
       "      <td>CHEMBL3662868</td>\n",
       "      <td>0.608696</td>\n",
       "      <td>COCCCN1C[C@H](C)N(C[C@H]1C)C(=O)N1Cc2c(NC(=O)c...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>4twp</td>\n",
       "      <td>2v7a_ligand_similar_199</td>\n",
       "      <td>CHEMBL3662869</td>\n",
       "      <td>0.634538</td>\n",
       "      <td>COCCN1C[C@H](C)N(C[C@H]1C)C(=O)N1Cc2c(NC(=O)c3...</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "    pdb              ligand_file      chembl_id  tanimoto_index  \\\n",
       "0  4twp  4twp_ligand_similar_196  CHEMBL3920052        0.844156   \n",
       "1  4twp  4twp_ligand_similar_469  CHEMBL3967380        0.607143   \n",
       "2  4twp  4twp_ligand_similar_139  CHEMBL3948865        0.866667   \n",
       "3  4twp  2v7a_ligand_similar_287  CHEMBL3662868        0.608696   \n",
       "4  4twp  2v7a_ligand_similar_199  CHEMBL3662869        0.634538   \n",
       "\n",
       "                                              smiles  \n",
       "0  N(C(=O)c1c(cccc1)Sc1cc2c(cc1)c(n[nH]2)/C=C/c1c...  \n",
       "1  c1cc(cc2c1c(n[nH]2)/C=C/c1ccccn1)Nc1ccccc1C(=O...  \n",
       "2  c1(NC(=O)c2c(cccc2)Sc2cc3c(cc2)c(n[nH]3)/C=C/c...  \n",
       "3  COCCCN1C[C@H](C)N(C[C@H]1C)C(=O)N1Cc2c(NC(=O)c...  \n",
       "4  COCCN1C[C@H](C)N(C[C@H]1C)C(=O)N1Cc2c(NC(=O)c3...  "
      ]
     },
     "execution_count": 91,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "all_ligands.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 92,
   "id": "ac703780-97cd-4f37-a105-833ef27df49f",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(1683, 4)"
      ]
     },
     "execution_count": 92,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_test_random_meta.shape"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 93,
   "id": "249dfb8f-620a-4365-86d2-ae4625be221e",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_random_meta = pd.concat([data_train_random_meta,data_test_random_meta])\n",
    "data_random_meta = data_random_meta.reset_index(drop=True)\n",
    "data_random = pd.concat([data_train_random,data_test_random])\n",
    "data_random = data_random.reset_index(drop=True)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 94,
   "id": "df363677-749b-4c6f-97f4-d13a0cb1f134",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "(8421, 4)\n",
      "(8421, 126)\n"
     ]
    }
   ],
   "source": [
    "print(data_random_meta.shape)\n",
    "print(data_random.shape)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 95,
   "id": "b5ee6956-3671-44d9-8eac-9ef71fb04036",
   "metadata": {},
   "outputs": [
    {
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       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>WeightDescriptor</th>\n",
       "      <th>RuleOfFiveDescriptorV0</th>\n",
       "      <th>RuleOfFiveDescriptorV1</th>\n",
       "      <th>RuleOfFiveDescriptorV2</th>\n",
       "      <th>RuleOfFiveDescriptorV3</th>\n",
       "      <th>RuleOfFiveDescriptorV4</th>\n",
       "      <th>RuleOfFiveDescriptorV5</th>\n",
       "      <th>RotatableBondsCountDescriptor</th>\n",
       "      <th>HBondDonorCountDescriptor</th>\n",
       "      <th>HBondAcceptorCountDescriptor</th>\n",
       "      <th>...</th>\n",
       "      <th>StrandSS</th>\n",
       "      <th>OtherSS</th>\n",
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       "      <th>DominantSSOther</th>\n",
       "      <th>BuriedASA</th>\n",
       "      <th>ExposedASA</th>\n",
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       "      <td>1515</td>\n",
       "      <td>-9.3</td>\n",
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       "      <th>1</th>\n",
       "      <td>608.7280</td>\n",
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       "      <td>0.3165</td>\n",
       "      <td>0.5316</td>\n",
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       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
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       "      <td>1515</td>\n",
       "      <td>-7.8</td>\n",
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       "      <td>586.9836</td>\n",
       "      <td>0</td>\n",
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       "      <td>10</td>\n",
       "      <td>2</td>\n",
       "      <td>11</td>\n",
       "      <td>...</td>\n",
       "      <td>0.3165</td>\n",
       "      <td>0.5316</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0</td>\n",
       "      <td>2067.8781</td>\n",
       "      <td>1515</td>\n",
       "      <td>-9.0</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>269.0821</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
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       "      <td>0.5316</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0</td>\n",
       "      <td>2067.8781</td>\n",
       "      <td>1515</td>\n",
       "      <td>-5.1</td>\n",
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       "    <tr>\n",
       "      <th>4</th>\n",
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       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0</td>\n",
       "      <td>2067.8781</td>\n",
       "      <td>1515</td>\n",
       "      <td>-9.8</td>\n",
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       "   WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "0          569.0146                       0                       0   \n",
       "1          608.7280                       0                       0   \n",
       "2          586.9836                       0                       0   \n",
       "3          269.0821                       1                       0   \n",
       "4          587.4635                       0                       0   \n",
       "\n",
       "   RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
       "0                       1                       0                       0   \n",
       "1                       1                       0                       0   \n",
       "2                       1                       0                       0   \n",
       "3                       0                       0                       0   \n",
       "4                       1                       0                       0   \n",
       "\n",
       "   RuleOfFiveDescriptorV5  RotatableBondsCountDescriptor  \\\n",
       "0                       0                             12   \n",
       "1                       0                             18   \n",
       "2                       0                             10   \n",
       "3                       0                              0   \n",
       "4                       0                             10   \n",
       "\n",
       "   HBondDonorCountDescriptor  HBondAcceptorCountDescriptor  ...  StrandSS  \\\n",
       "0                          3                             9  ...    0.3165   \n",
       "1                          4                             7  ...    0.3165   \n",
       "2                          2                            11  ...    0.3165   \n",
       "3                          0                             1  ...    0.3165   \n",
       "4                          5                             8  ...    0.3165   \n",
       "\n",
       "   OtherSS  DominantSSHelix  DominantSSOther  BuriedASA  ExposedASA  RatioASA  \\\n",
       "0   0.5316                0                1     0.6667      0.3333       2.0   \n",
       "1   0.5316                0                1     0.6667      0.3333       2.0   \n",
       "2   0.5316                0                1     0.6667      0.3333       2.0   \n",
       "3   0.5316                0                1     0.6667      0.3333       2.0   \n",
       "4   0.5316                0                1     0.6667      0.3333       2.0   \n",
       "\n",
       "   PocketASA  volume   ba  \n",
       "0  2067.8781    1515 -9.3  \n",
       "1  2067.8781    1515 -7.8  \n",
       "2  2067.8781    1515 -9.0  \n",
       "3  2067.8781    1515 -5.1  \n",
       "4  2067.8781    1515 -9.8  \n",
       "\n",
       "[5 rows x 126 columns]"
      ]
     },
     "execution_count": 95,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 96,
   "id": "5e686d24-1b2a-42ba-960b-f0ab4cb5010c",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
       "      <th>chembl_id</th>\n",
       "      <th>tanimoto_index</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4crc_ligand_similar_77</td>\n",
       "      <td>CHEMBL3398642</td>\n",
       "      <td>0.627706</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cra_ligand_similar_145</td>\n",
       "      <td>CHEMBL3984836</td>\n",
       "      <td>0.606897</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4crc_ligand_similar_37</td>\n",
       "      <td>CHEMBL4101257</td>\n",
       "      <td>0.687500</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cr9_ligand_similar_191</td>\n",
       "      <td>CHEMBL1882875</td>\n",
       "      <td>0.603774</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4ty7_ligand_similar_44</td>\n",
       "      <td>CHEMBL3398638</td>\n",
       "      <td>0.683983</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "    pdb              ligand_file      chembl_id  tanimoto_index\n",
       "0  4crc   4crc_ligand_similar_77  CHEMBL3398642        0.627706\n",
       "1  4crc  4cra_ligand_similar_145  CHEMBL3984836        0.606897\n",
       "2  4crc   4crc_ligand_similar_37  CHEMBL4101257        0.687500\n",
       "3  4crc  4cr9_ligand_similar_191  CHEMBL1882875        0.603774\n",
       "4  4crc   4ty7_ligand_similar_44  CHEMBL3398638        0.683983"
      ]
     },
     "execution_count": 96,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random_meta.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 97,
   "id": "b1313f9f-74c4-4bbe-aa73-33c3897cac35",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_random = pd.concat([data_random_meta, data_random], axis=1, join=\"inner\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 98,
   "id": "cf37ab1f-0c15-46e5-a6e0-a5db2ffc92de",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(8421, 130)"
      ]
     },
     "execution_count": 98,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.shape"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 99,
   "id": "c53c5a18-2434-4eea-a863-9ac0a4138466",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
       "      <th>chembl_id</th>\n",
       "      <th>tanimoto_index</th>\n",
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       "      <th>RuleOfFiveDescriptorV4</th>\n",
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       "      <th>1</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cra_ligand_similar_145</td>\n",
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       "      <td>608.7280</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
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       "      <td>4crc</td>\n",
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       "      <td>CHEMBL1882875</td>\n",
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       "    pdb              ligand_file      chembl_id  tanimoto_index  \\\n",
       "0  4crc   4crc_ligand_similar_77  CHEMBL3398642        0.627706   \n",
       "1  4crc  4cra_ligand_similar_145  CHEMBL3984836        0.606897   \n",
       "2  4crc   4crc_ligand_similar_37  CHEMBL4101257        0.687500   \n",
       "3  4crc  4cr9_ligand_similar_191  CHEMBL1882875        0.603774   \n",
       "4  4crc   4ty7_ligand_similar_44  CHEMBL3398638        0.683983   \n",
       "\n",
       "   WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "0          569.0146                       0                       0   \n",
       "1          608.7280                       0                       0   \n",
       "2          586.9836                       0                       0   \n",
       "3          269.0821                       1                       0   \n",
       "4          587.4635                       0                       0   \n",
       "\n",
       "   RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
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       "1                       1                       0                       0   \n",
       "2                       1                       0                       0   \n",
       "3                       0                       0                       0   \n",
       "4                       1                       0                       0   \n",
       "\n",
       "   ...  StrandSS  OtherSS  DominantSSHelix  DominantSSOther  BuriedASA  \\\n",
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       "1  ...    0.3165   0.5316                0                1     0.6667   \n",
       "2  ...    0.3165   0.5316                0                1     0.6667   \n",
       "3  ...    0.3165   0.5316                0                1     0.6667   \n",
       "4  ...    0.3165   0.5316                0                1     0.6667   \n",
       "\n",
       "   ExposedASA  RatioASA  PocketASA  volume   ba  \n",
       "0      0.3333       2.0  2067.8781    1515 -9.3  \n",
       "1      0.3333       2.0  2067.8781    1515 -7.8  \n",
       "2      0.3333       2.0  2067.8781    1515 -9.0  \n",
       "3      0.3333       2.0  2067.8781    1515 -5.1  \n",
       "4      0.3333       2.0  2067.8781    1515 -9.8  \n",
       "\n",
       "[5 rows x 130 columns]"
      ]
     },
     "execution_count": 99,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 100,
   "id": "3cd82af9-b7f9-41f8-b160-ae4ffb8b2421",
   "metadata": {},
   "outputs": [
    {
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       "      <th>124</th>\n",
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       "      <td>4cr9_ligand_similar_37</td>\n",
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       "      <td>...</td>\n",
       "      <td>0.2868</td>\n",
       "      <td>0.5659</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.8810</td>\n",
       "      <td>0.1190</td>\n",
       "      <td>7.4000</td>\n",
       "      <td>558.1279</td>\n",
       "      <td>1037</td>\n",
       "      <td>-6.9</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>6159</th>\n",
       "      <td>4gr0</td>\n",
       "      <td>3lka_ligand_similar_82</td>\n",
       "      <td>CHEMBL6648</td>\n",
       "      <td>0.619048</td>\n",
       "      <td>207.2504</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.1698</td>\n",
       "      <td>0.5912</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.5455</td>\n",
       "      <td>0.4545</td>\n",
       "      <td>1.2000</td>\n",
       "      <td>2462.5177</td>\n",
       "      <td>1456</td>\n",
       "      <td>-7.2</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>210 rows × 130 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "       pdb              ligand_file      chembl_id  tanimoto_index  \\\n",
       "3505  4wiv   4ogj_ligand_similar_27   CHEMBL101473        0.616883   \n",
       "5096  3up2  3up2_ligand_similar_272   CHEMBL101473        0.607692   \n",
       "7339  4jia  4e6q_ligand_similar_150   CHEMBL102648        0.656250   \n",
       "2137  4e5w  4e5w_ligand_similar_119   CHEMBL102648        0.639706   \n",
       "1977  4e5w   4e5w_ligand_similar_44  CHEMBL1088346        0.692982   \n",
       "...    ...                      ...            ...             ...   \n",
       "105   4crc   4cr9_ligand_similar_42   CHEMBL528924        0.690909   \n",
       "124   4crc   4cr9_ligand_similar_37    CHEMBL62083        0.697674   \n",
       "6527  3utu   1bcu_ligand_similar_99    CHEMBL62083        0.757576   \n",
       "5859  2weg    2weg_ligand_similar_8     CHEMBL6648        0.702703   \n",
       "6159  4gr0   3lka_ligand_similar_82     CHEMBL6648        0.619048   \n",
       "\n",
       "      WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "3505          393.4829                       1                       0   \n",
       "5096          393.4829                       1                       0   \n",
       "7339          420.5083                       1                       0   \n",
       "2137          420.5083                       1                       0   \n",
       "1977          344.4536                       1                       0   \n",
       "...                ...                     ...                     ...   \n",
       "105           235.2844                       1                       0   \n",
       "124           144.1736                       1                       0   \n",
       "6527          144.1736                       1                       0   \n",
       "5859          207.2504                       1                       0   \n",
       "6159          207.2504                       1                       0   \n",
       "\n",
       "      RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
       "3505                       0                       0                       0   \n",
       "5096                       0                       0                       0   \n",
       "7339                       0                       0                       0   \n",
       "2137                       0                       0                       0   \n",
       "1977                       0                       0                       0   \n",
       "...                      ...                     ...                     ...   \n",
       "105                        0                       0                       0   \n",
       "124                        0                       0                       0   \n",
       "6527                       0                       0                       0   \n",
       "5859                       0                       0                       0   \n",
       "6159                       0                       0                       0   \n",
       "\n",
       "      ...  StrandSS  OtherSS  DominantSSHelix  DominantSSOther  BuriedASA  \\\n",
       "3505  ...    0.0000   0.4882                1                0     0.5278   \n",
       "5096  ...    0.1579   0.4549                0                1     0.5682   \n",
       "7339  ...    0.1733   0.3900                1                0     0.5476   \n",
       "2137  ...    0.1951   0.3885                1                0     0.6792   \n",
       "1977  ...    0.1951   0.3885                1                0     0.6792   \n",
       "...   ...       ...      ...              ...              ...        ...   \n",
       "105   ...    0.3165   0.5316                0                1     0.6667   \n",
       "124   ...    0.3165   0.5316                0                1     0.6667   \n",
       "6527  ...    0.2945   0.5273                0                1     0.6140   \n",
       "5859  ...    0.2868   0.5659                0                1     0.8810   \n",
       "6159  ...    0.1698   0.5912                0                1     0.5455   \n",
       "\n",
       "      ExposedASA  RatioASA  PocketASA  volume   ba  \n",
       "3505      0.4722    1.1176  1588.9832    1095 -7.7  \n",
       "5096      0.4318    1.3158  1564.6148    1293 -8.3  \n",
       "7339      0.4524    1.2105  1744.1005    1048 -8.0  \n",
       "2137      0.3208    2.1176  3547.2605    1506 -7.1  \n",
       "1977      0.3208    2.1176  3547.2605    1506 -7.4  \n",
       "...          ...       ...        ...     ...  ...  \n",
       "105       0.3333    2.0000  2067.8781    1515 -8.0  \n",
       "124       0.3333    2.0000  2067.8781    1515 -6.5  \n",
       "6527      0.3860    1.5909  2236.5199    1518 -7.9  \n",
       "5859      0.1190    7.4000   558.1279    1037 -6.9  \n",
       "6159      0.4545    1.2000  2462.5177    1456 -7.2  \n",
       "\n",
       "[210 rows x 130 columns]"
      ]
     },
     "execution_count": 100,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "ids = data_random[\"chembl_id\"]\n",
    "data_random[ids.isin(ids[ids.duplicated()])].sort_values(\"chembl_id\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 101,
   "id": "262795d0-88e4-4285-8347-59ab5dd7d8cf",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_random = data_random.merge(all_ligands[[\"chembl_id\", \"smiles\"]], on=\"chembl_id\", how=\"left\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 102,
   "id": "640aa1a6-3879-4096-9706-b194bdeeb639",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_random[\"ID\"] = data_random[[\"pdb\", \"ligand_file\", \"chembl_id\"]].apply(\"-\".join, axis=1)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 103,
   "id": "fb2bad65-9301-4f21-9d33-f793115c3ec7",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
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       "      <th>3</th>\n",
       "      <td>4crc</td>\n",
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       "      <td>CHEMBL4101257</td>\n",
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       "      <th>4</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cr9_ligand_similar_191</td>\n",
       "      <td>CHEMBL1882875</td>\n",
       "      <td>0.603774</td>\n",
       "      <td>269.0821</td>\n",
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      "text/plain": [
       "    pdb              ligand_file      chembl_id  tanimoto_index  \\\n",
       "0  4crc   4crc_ligand_similar_77  CHEMBL3398642        0.627706   \n",
       "1  4crc  4cra_ligand_similar_145  CHEMBL3984836        0.606897   \n",
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       "4  4crc  4cr9_ligand_similar_191  CHEMBL1882875        0.603774   \n",
       "\n",
       "   WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "0          569.0146                       0                       0   \n",
       "1          608.7280                       0                       0   \n",
       "2          608.7280                       0                       0   \n",
       "3          586.9836                       0                       0   \n",
       "4          269.0821                       1                       0   \n",
       "\n",
       "   RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
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       "1                       1                       0                       0   \n",
       "2                       1                       0                       0   \n",
       "3                       1                       0                       0   \n",
       "4                       0                       0                       0   \n",
       "\n",
       "   ...  DominantSSHelix  DominantSSOther  BuriedASA  ExposedASA  RatioASA  \\\n",
       "0  ...                0                1     0.6667      0.3333       2.0   \n",
       "1  ...                0                1     0.6667      0.3333       2.0   \n",
       "2  ...                0                1     0.6667      0.3333       2.0   \n",
       "3  ...                0                1     0.6667      0.3333       2.0   \n",
       "4  ...                0                1     0.6667      0.3333       2.0   \n",
       "\n",
       "   PocketASA  volume   ba                                             smiles  \\\n",
       "0  2067.8781    1515 -9.3  c1c(cccc1)C[C@H](NC(=O)/C=C/c1c(ccc(c1)Cl)n1nn...   \n",
       "1  2067.8781    1515 -7.8  CCOc1ccc(C[C@@H](NC(=O)c2ccc(OC)cc2)C(=O)N[C@@...   \n",
       "2  2067.8781    1515 -7.8  CCOc1ccc(C[C@@H](NC(=O)c2ccc(OC)cc2)C(=O)N[C@@...   \n",
       "3  2067.8781    1515 -9.0  c1cc(cc(c1n1cnnn1)/C=C/C(=O)N1C(C(=O)Nc2ccc(cc...   \n",
       "4  2067.8781    1515 -5.1                                 Ic1cc2c(nccc2C)cc1   \n",
       "\n",
       "                                           ID  \n",
       "0   4crc-4crc_ligand_similar_77-CHEMBL3398642  \n",
       "1  4crc-4cra_ligand_similar_145-CHEMBL3984836  \n",
       "2  4crc-4cra_ligand_similar_145-CHEMBL3984836  \n",
       "3   4crc-4crc_ligand_similar_37-CHEMBL4101257  \n",
       "4  4crc-4cr9_ligand_similar_191-CHEMBL1882875  \n",
       "\n",
       "[5 rows x 132 columns]"
      ]
     },
     "execution_count": 103,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 104,
   "id": "36226d00-6cf2-46d7-a13c-7a83854d36cf",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "      <th>3882</th>\n",
       "      <td>4wiv</td>\n",
       "      <td>4ogj_ligand_similar_27</td>\n",
       "      <td>CHEMBL101473</td>\n",
       "      <td>0.616883</td>\n",
       "      <td>393.4829</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0.5278</td>\n",
       "      <td>0.4722</td>\n",
       "      <td>1.1176</td>\n",
       "      <td>1588.9832</td>\n",
       "      <td>1095</td>\n",
       "      <td>-7.7</td>\n",
       "      <td>n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1</td>\n",
       "      <td>4wiv-4ogj_ligand_similar_27-CHEMBL101473</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>5475</th>\n",
       "      <td>3up2</td>\n",
       "      <td>3up2_ligand_similar_272</td>\n",
       "      <td>CHEMBL101473</td>\n",
       "      <td>0.607692</td>\n",
       "      <td>393.4829</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.5682</td>\n",
       "      <td>0.4318</td>\n",
       "      <td>1.3158</td>\n",
       "      <td>1564.6148</td>\n",
       "      <td>1293</td>\n",
       "      <td>-8.3</td>\n",
       "      <td>n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1</td>\n",
       "      <td>3up2-3up2_ligand_similar_272-CHEMBL101473</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2356</th>\n",
       "      <td>4e5w</td>\n",
       "      <td>4e5w_ligand_similar_119</td>\n",
       "      <td>CHEMBL102648</td>\n",
       "      <td>0.639706</td>\n",
       "      <td>420.5083</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0.6792</td>\n",
       "      <td>0.3208</td>\n",
       "      <td>2.1176</td>\n",
       "      <td>3547.2605</td>\n",
       "      <td>1506</td>\n",
       "      <td>-7.1</td>\n",
       "      <td>n1(c(nc2c1ccnc2)C)CC1CCN(C(=O)CN(C(=O)c2ccc(N)...</td>\n",
       "      <td>4e5w-4e5w_ligand_similar_119-CHEMBL102648</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>...</th>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>57</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cra_ligand_similar_38</td>\n",
       "      <td>CHEMBL68225</td>\n",
       "      <td>0.635762</td>\n",
       "      <td>508.6119</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0000</td>\n",
       "      <td>2067.8781</td>\n",
       "      <td>1515</td>\n",
       "      <td>-9.2</td>\n",
       "      <td>c1(C(=O)N2C(C(=O)N[C@@H](C(=O)N(Cc3ccccc3)C)Cc...</td>\n",
       "      <td>4crc-4cra_ligand_similar_38-CHEMBL68225</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>930</th>\n",
       "      <td>2hb1</td>\n",
       "      <td>1bzc_ligand_similar_177</td>\n",
       "      <td>CHEMBL96012</td>\n",
       "      <td>0.611111</td>\n",
       "      <td>248.3213</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0000</td>\n",
       "      <td>1403.5820</td>\n",
       "      <td>1039</td>\n",
       "      <td>-6.3</td>\n",
       "      <td>C(=O)(NCc1ccccc1)C(NC(=O)C)CCC</td>\n",
       "      <td>2hb1-1bzc_ligand_similar_177-CHEMBL96012</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>929</th>\n",
       "      <td>2hb1</td>\n",
       "      <td>1bzc_ligand_similar_177</td>\n",
       "      <td>CHEMBL96012</td>\n",
       "      <td>0.611111</td>\n",
       "      <td>248.3213</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0000</td>\n",
       "      <td>1403.5820</td>\n",
       "      <td>1039</td>\n",
       "      <td>-6.3</td>\n",
       "      <td>C(=O)(NCc1ccccc1)C(NC(=O)C)CCC</td>\n",
       "      <td>2hb1-1bzc_ligand_similar_177-CHEMBL96012</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>191</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cr9_ligand_similar_185</td>\n",
       "      <td>CHEMBL99408</td>\n",
       "      <td>0.604651</td>\n",
       "      <td>144.1736</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0000</td>\n",
       "      <td>2067.8781</td>\n",
       "      <td>1515</td>\n",
       "      <td>-5.9</td>\n",
       "      <td>Nc1ccc2ncccc2c1</td>\n",
       "      <td>4crc-4cr9_ligand_similar_185-CHEMBL99408</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>190</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cr9_ligand_similar_185</td>\n",
       "      <td>CHEMBL99408</td>\n",
       "      <td>0.604651</td>\n",
       "      <td>144.1736</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0000</td>\n",
       "      <td>2067.8781</td>\n",
       "      <td>1515</td>\n",
       "      <td>-5.9</td>\n",
       "      <td>Nc1ccc2ncccc2c1</td>\n",
       "      <td>4crc-4cr9_ligand_similar_185-CHEMBL99408</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>1054 rows × 132 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "       pdb              ligand_file     chembl_id  tanimoto_index  \\\n",
       "5476  3up2  3up2_ligand_similar_272  CHEMBL101473        0.607692   \n",
       "3883  4wiv   4ogj_ligand_similar_27  CHEMBL101473        0.616883   \n",
       "3882  4wiv   4ogj_ligand_similar_27  CHEMBL101473        0.616883   \n",
       "5475  3up2  3up2_ligand_similar_272  CHEMBL101473        0.607692   \n",
       "2356  4e5w  4e5w_ligand_similar_119  CHEMBL102648        0.639706   \n",
       "...    ...                      ...           ...             ...   \n",
       "57    4crc   4cra_ligand_similar_38   CHEMBL68225        0.635762   \n",
       "930   2hb1  1bzc_ligand_similar_177   CHEMBL96012        0.611111   \n",
       "929   2hb1  1bzc_ligand_similar_177   CHEMBL96012        0.611111   \n",
       "191   4crc  4cr9_ligand_similar_185   CHEMBL99408        0.604651   \n",
       "190   4crc  4cr9_ligand_similar_185   CHEMBL99408        0.604651   \n",
       "\n",
       "      WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "5476          393.4829                       1                       0   \n",
       "3883          393.4829                       1                       0   \n",
       "3882          393.4829                       1                       0   \n",
       "5475          393.4829                       1                       0   \n",
       "2356          420.5083                       1                       0   \n",
       "...                ...                     ...                     ...   \n",
       "57            508.6119                       0                       1   \n",
       "930           248.3213                       1                       0   \n",
       "929           248.3213                       1                       0   \n",
       "191           144.1736                       1                       0   \n",
       "190           144.1736                       1                       0   \n",
       "\n",
       "      RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
       "5476                       0                       0                       0   \n",
       "3883                       0                       0                       0   \n",
       "3882                       0                       0                       0   \n",
       "5475                       0                       0                       0   \n",
       "2356                       0                       0                       0   \n",
       "...                      ...                     ...                     ...   \n",
       "57                         0                       0                       0   \n",
       "930                        0                       0                       0   \n",
       "929                        0                       0                       0   \n",
       "191                        0                       0                       0   \n",
       "190                        0                       0                       0   \n",
       "\n",
       "      ...  DominantSSHelix  DominantSSOther  BuriedASA  ExposedASA  RatioASA  \\\n",
       "5476  ...                0                1     0.5682      0.4318    1.3158   \n",
       "3883  ...                1                0     0.5278      0.4722    1.1176   \n",
       "3882  ...                1                0     0.5278      0.4722    1.1176   \n",
       "5475  ...                0                1     0.5682      0.4318    1.3158   \n",
       "2356  ...                1                0     0.6792      0.3208    2.1176   \n",
       "...   ...              ...              ...        ...         ...       ...   \n",
       "57    ...                0                1     0.6667      0.3333    2.0000   \n",
       "930   ...                0                1     0.6667      0.3333    2.0000   \n",
       "929   ...                0                1     0.6667      0.3333    2.0000   \n",
       "191   ...                0                1     0.6667      0.3333    2.0000   \n",
       "190   ...                0                1     0.6667      0.3333    2.0000   \n",
       "\n",
       "      PocketASA  volume   ba  \\\n",
       "5476  1564.6148    1293 -8.3   \n",
       "3883  1588.9832    1095 -7.7   \n",
       "3882  1588.9832    1095 -7.7   \n",
       "5475  1564.6148    1293 -8.3   \n",
       "2356  3547.2605    1506 -7.1   \n",
       "...         ...     ...  ...   \n",
       "57    2067.8781    1515 -9.2   \n",
       "930   1403.5820    1039 -6.3   \n",
       "929   1403.5820    1039 -6.3   \n",
       "191   2067.8781    1515 -5.9   \n",
       "190   2067.8781    1515 -5.9   \n",
       "\n",
       "                                                 smiles  \\\n",
       "5476      n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1   \n",
       "3883      n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1   \n",
       "3882      n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1   \n",
       "5475      n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1   \n",
       "2356  n1(c(nc2c1ccnc2)C)CC1CCN(C(=O)CN(C(=O)c2ccc(N)...   \n",
       "...                                                 ...   \n",
       "57    c1(C(=O)N2C(C(=O)N[C@@H](C(=O)N(Cc3ccccc3)C)Cc...   \n",
       "930                      C(=O)(NCc1ccccc1)C(NC(=O)C)CCC   \n",
       "929                      C(=O)(NCc1ccccc1)C(NC(=O)C)CCC   \n",
       "191                                     Nc1ccc2ncccc2c1   \n",
       "190                                     Nc1ccc2ncccc2c1   \n",
       "\n",
       "                                             ID  \n",
       "5476  3up2-3up2_ligand_similar_272-CHEMBL101473  \n",
       "3883   4wiv-4ogj_ligand_similar_27-CHEMBL101473  \n",
       "3882   4wiv-4ogj_ligand_similar_27-CHEMBL101473  \n",
       "5475  3up2-3up2_ligand_similar_272-CHEMBL101473  \n",
       "2356  4e5w-4e5w_ligand_similar_119-CHEMBL102648  \n",
       "...                                         ...  \n",
       "57      4crc-4cra_ligand_similar_38-CHEMBL68225  \n",
       "930    2hb1-1bzc_ligand_similar_177-CHEMBL96012  \n",
       "929    2hb1-1bzc_ligand_similar_177-CHEMBL96012  \n",
       "191    4crc-4cr9_ligand_similar_185-CHEMBL99408  \n",
       "190    4crc-4cr9_ligand_similar_185-CHEMBL99408  \n",
       "\n",
       "[1054 rows x 132 columns]"
      ]
     },
     "execution_count": 104,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "ids = data_random[\"chembl_id\"]\n",
    "data_random[ids.isin(ids[ids.duplicated()])].sort_values(\"chembl_id\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 105,
   "id": "4376594f-ff04-4308-ab5f-c01e38709cf3",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_random = data_random.groupby('ID').first()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 107,
   "id": "d37884ec-e22d-4118-814d-34e049bc591d",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(8421, 131)"
      ]
     },
     "execution_count": 107,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.shape"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 108,
   "id": "e646f7fb-fd29-44bb-8ac7-f2dd8442ebfb",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
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       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
       "      <th>chembl_id</th>\n",
       "      <th>tanimoto_index</th>\n",
       "      <th>WeightDescriptor</th>\n",
       "      <th>RuleOfFiveDescriptorV0</th>\n",
       "      <th>RuleOfFiveDescriptorV1</th>\n",
       "      <th>RuleOfFiveDescriptorV2</th>\n",
       "      <th>RuleOfFiveDescriptorV3</th>\n",
       "      <th>RuleOfFiveDescriptorV4</th>\n",
       "      <th>...</th>\n",
       "      <th>OtherSS</th>\n",
       "      <th>DominantSSHelix</th>\n",
       "      <th>DominantSSOther</th>\n",
       "      <th>BuriedASA</th>\n",
       "      <th>ExposedASA</th>\n",
       "      <th>RatioASA</th>\n",
       "      <th>PocketASA</th>\n",
       "      <th>volume</th>\n",
       "      <th>ba</th>\n",
       "      <th>smiles</th>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>ID</th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
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       "      <th></th>\n",
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       "      <th></th>\n",
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       "      <th></th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
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       "      <th></th>\n",
       "      <th></th>\n",
       "      <th></th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>4wiv-4ogj_ligand_similar_27-CHEMBL101473</th>\n",
       "      <td>4wiv</td>\n",
       "      <td>4ogj_ligand_similar_27</td>\n",
       "      <td>CHEMBL101473</td>\n",
       "      <td>0.616883</td>\n",
       "      <td>393.4829</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.4882</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0.5278</td>\n",
       "      <td>0.4722</td>\n",
       "      <td>1.1176</td>\n",
       "      <td>1588.9832</td>\n",
       "      <td>1095</td>\n",
       "      <td>-7.7</td>\n",
       "      <td>n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3up2-3up2_ligand_similar_272-CHEMBL101473</th>\n",
       "      <td>3up2</td>\n",
       "      <td>3up2_ligand_similar_272</td>\n",
       "      <td>CHEMBL101473</td>\n",
       "      <td>0.607692</td>\n",
       "      <td>393.4829</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.4549</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.5682</td>\n",
       "      <td>0.4318</td>\n",
       "      <td>1.3158</td>\n",
       "      <td>1564.6148</td>\n",
       "      <td>1293</td>\n",
       "      <td>-8.3</td>\n",
       "      <td>n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4e5w-4e5w_ligand_similar_119-CHEMBL102648</th>\n",
       "      <td>4e5w</td>\n",
       "      <td>4e5w_ligand_similar_119</td>\n",
       "      <td>CHEMBL102648</td>\n",
       "      <td>0.639706</td>\n",
       "      <td>420.5083</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.3885</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0.6792</td>\n",
       "      <td>0.3208</td>\n",
       "      <td>2.1176</td>\n",
       "      <td>3547.2605</td>\n",
       "      <td>1506</td>\n",
       "      <td>-7.1</td>\n",
       "      <td>n1(c(nc2c1ccnc2)C)CC1CCN(C(=O)CN(C(=O)c2ccc(N)...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4jia-4e6q_ligand_similar_150-CHEMBL102648</th>\n",
       "      <td>4jia</td>\n",
       "      <td>4e6q_ligand_similar_150</td>\n",
       "      <td>CHEMBL102648</td>\n",
       "      <td>0.656250</td>\n",
       "      <td>420.5083</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.3900</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0.5476</td>\n",
       "      <td>0.4524</td>\n",
       "      <td>1.2105</td>\n",
       "      <td>1744.1005</td>\n",
       "      <td>1048</td>\n",
       "      <td>-8.0</td>\n",
       "      <td>n1(c(nc2c1ccnc2)C)CC1CCN(C(=O)CN(C(=O)c2ccc(N)...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4e5w-4e5w_ligand_similar_44-CHEMBL1088346</th>\n",
       "      <td>4e5w</td>\n",
       "      <td>4e5w_ligand_similar_44</td>\n",
       "      <td>CHEMBL1088346</td>\n",
       "      <td>0.692982</td>\n",
       "      <td>344.4536</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.3885</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0.6792</td>\n",
       "      <td>0.3208</td>\n",
       "      <td>2.1176</td>\n",
       "      <td>3547.2605</td>\n",
       "      <td>1506</td>\n",
       "      <td>-7.4</td>\n",
       "      <td>n1c2c(nc3ccccc13)c1ccccc1n2CCN1C(CCCC1)C</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>...</th>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3udh-3rsx_ligand_similar_32-CHEMBL528924</th>\n",
       "      <td>3udh</td>\n",
       "      <td>3rsx_ligand_similar_32</td>\n",
       "      <td>CHEMBL528924</td>\n",
       "      <td>0.616438</td>\n",
       "      <td>235.2844</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.4619</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6341</td>\n",
       "      <td>0.3659</td>\n",
       "      <td>1.7333</td>\n",
       "      <td>1291.3232</td>\n",
       "      <td>414</td>\n",
       "      <td>-8.6</td>\n",
       "      <td>Nc1cccc(c1)c1ccc2ccnc(N)c2c1</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4crc-4cr9_ligand_similar_37-CHEMBL62083</th>\n",
       "      <td>4crc</td>\n",
       "      <td>4cr9_ligand_similar_37</td>\n",
       "      <td>CHEMBL62083</td>\n",
       "      <td>0.697674</td>\n",
       "      <td>144.1736</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5316</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6667</td>\n",
       "      <td>0.3333</td>\n",
       "      <td>2.0000</td>\n",
       "      <td>2067.8781</td>\n",
       "      <td>1515</td>\n",
       "      <td>-6.5</td>\n",
       "      <td>Nc1nccc2ccccc12</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3utu-1bcu_ligand_similar_99-CHEMBL62083</th>\n",
       "      <td>3utu</td>\n",
       "      <td>1bcu_ligand_similar_99</td>\n",
       "      <td>CHEMBL62083</td>\n",
       "      <td>0.757576</td>\n",
       "      <td>144.1736</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5273</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6140</td>\n",
       "      <td>0.3860</td>\n",
       "      <td>1.5909</td>\n",
       "      <td>2236.5199</td>\n",
       "      <td>1518</td>\n",
       "      <td>-7.9</td>\n",
       "      <td>Nc1nccc2ccccc12</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4gr0-3lka_ligand_similar_82-CHEMBL6648</th>\n",
       "      <td>4gr0</td>\n",
       "      <td>3lka_ligand_similar_82</td>\n",
       "      <td>CHEMBL6648</td>\n",
       "      <td>0.619048</td>\n",
       "      <td>207.2504</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5912</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.5455</td>\n",
       "      <td>0.4545</td>\n",
       "      <td>1.2000</td>\n",
       "      <td>2462.5177</td>\n",
       "      <td>1456</td>\n",
       "      <td>-7.2</td>\n",
       "      <td>c1ccc2c(c1)c(ccc2)S(=O)(=O)N</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2weg-2weg_ligand_similar_8-CHEMBL6648</th>\n",
       "      <td>2weg</td>\n",
       "      <td>2weg_ligand_similar_8</td>\n",
       "      <td>CHEMBL6648</td>\n",
       "      <td>0.702703</td>\n",
       "      <td>207.2504</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5659</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.8810</td>\n",
       "      <td>0.1190</td>\n",
       "      <td>7.4000</td>\n",
       "      <td>558.1279</td>\n",
       "      <td>1037</td>\n",
       "      <td>-6.9</td>\n",
       "      <td>c1ccc2c(c1)c(ccc2)S(=O)(=O)N</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>210 rows × 131 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "                                            pdb              ligand_file  \\\n",
       "ID                                                                         \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473   4wiv   4ogj_ligand_similar_27   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473  3up2  3up2_ligand_similar_272   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648  4e5w  4e5w_ligand_similar_119   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648  4jia  4e6q_ligand_similar_150   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346  4e5w   4e5w_ligand_similar_44   \n",
       "...                                         ...                      ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924   3udh   3rsx_ligand_similar_32   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083    4crc   4cr9_ligand_similar_37   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083    3utu   1bcu_ligand_similar_99   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648     4gr0   3lka_ligand_similar_82   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648      2weg    2weg_ligand_similar_8   \n",
       "\n",
       "                                               chembl_id  tanimoto_index  \\\n",
       "ID                                                                         \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473    CHEMBL101473        0.616883   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473   CHEMBL101473        0.607692   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648   CHEMBL102648        0.639706   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648   CHEMBL102648        0.656250   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346  CHEMBL1088346        0.692982   \n",
       "...                                                  ...             ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924    CHEMBL528924        0.616438   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083      CHEMBL62083        0.697674   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083      CHEMBL62083        0.757576   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648        CHEMBL6648        0.619048   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648         CHEMBL6648        0.702703   \n",
       "\n",
       "                                           WeightDescriptor  \\\n",
       "ID                                                            \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473           393.4829   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473          393.4829   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648          420.5083   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648          420.5083   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346          344.4536   \n",
       "...                                                     ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924           235.2844   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083            144.1736   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083            144.1736   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648             207.2504   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648              207.2504   \n",
       "\n",
       "                                           RuleOfFiveDescriptorV0  \\\n",
       "ID                                                                  \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473                        1   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473                       1   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648                       1   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648                       1   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346                       1   \n",
       "...                                                           ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924                        1   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083                         1   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083                         1   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648                          1   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648                           1   \n",
       "\n",
       "                                           RuleOfFiveDescriptorV1  \\\n",
       "ID                                                                  \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473                        0   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473                       0   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648                       0   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648                       0   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346                       0   \n",
       "...                                                           ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924                        0   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083                         0   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083                         0   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648                          0   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648                           0   \n",
       "\n",
       "                                           RuleOfFiveDescriptorV2  \\\n",
       "ID                                                                  \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473                        0   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473                       0   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648                       0   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648                       0   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346                       0   \n",
       "...                                                           ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924                        0   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083                         0   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083                         0   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648                          0   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648                           0   \n",
       "\n",
       "                                           RuleOfFiveDescriptorV3  \\\n",
       "ID                                                                  \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473                        0   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473                       0   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648                       0   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648                       0   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346                       0   \n",
       "...                                                           ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924                        0   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083                         0   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083                         0   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648                          0   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648                           0   \n",
       "\n",
       "                                           RuleOfFiveDescriptorV4  ...  \\\n",
       "ID                                                                 ...   \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473                        0  ...   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473                       0  ...   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648                       0  ...   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648                       0  ...   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346                       0  ...   \n",
       "...                                                           ...  ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924                        0  ...   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083                         0  ...   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083                         0  ...   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648                          0  ...   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648                           0  ...   \n",
       "\n",
       "                                           OtherSS  DominantSSHelix  \\\n",
       "ID                                                                    \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473    0.4882                1   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473   0.4549                0   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648   0.3885                1   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648   0.3900                1   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346   0.3885                1   \n",
       "...                                            ...              ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924    0.4619                0   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083     0.5316                0   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083     0.5273                0   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648      0.5912                0   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648       0.5659                0   \n",
       "\n",
       "                                           DominantSSOther  BuriedASA  \\\n",
       "ID                                                                      \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473                 0     0.5278   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473                1     0.5682   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648                0     0.6792   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648                0     0.5476   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346                0     0.6792   \n",
       "...                                                    ...        ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924                 1     0.6341   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083                  1     0.6667   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083                  1     0.6140   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648                   1     0.5455   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648                    1     0.8810   \n",
       "\n",
       "                                           ExposedASA  RatioASA  PocketASA  \\\n",
       "ID                                                                           \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473       0.4722    1.1176  1588.9832   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473      0.4318    1.3158  1564.6148   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648      0.3208    2.1176  3547.2605   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648      0.4524    1.2105  1744.1005   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346      0.3208    2.1176  3547.2605   \n",
       "...                                               ...       ...        ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924       0.3659    1.7333  1291.3232   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083        0.3333    2.0000  2067.8781   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083        0.3860    1.5909  2236.5199   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648         0.4545    1.2000  2462.5177   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648          0.1190    7.4000   558.1279   \n",
       "\n",
       "                                           volume   ba  \\\n",
       "ID                                                       \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473     1095 -7.7   \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473    1293 -8.3   \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648    1506 -7.1   \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648    1048 -8.0   \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346    1506 -7.4   \n",
       "...                                           ...  ...   \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924      414 -8.6   \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083      1515 -6.5   \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083      1518 -7.9   \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648       1456 -7.2   \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648        1037 -6.9   \n",
       "\n",
       "                                                                                      smiles  \n",
       "ID                                                                                            \n",
       "4wiv-4ogj_ligand_similar_27-CHEMBL101473       n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1  \n",
       "3up2-3up2_ligand_similar_272-CHEMBL101473      n1c(c(cnc1Nc1ccc(OCC(CN(C)C)O)cc1)C)Nc1ccccc1  \n",
       "4e5w-4e5w_ligand_similar_119-CHEMBL102648  n1(c(nc2c1ccnc2)C)CC1CCN(C(=O)CN(C(=O)c2ccc(N)...  \n",
       "4jia-4e6q_ligand_similar_150-CHEMBL102648  n1(c(nc2c1ccnc2)C)CC1CCN(C(=O)CN(C(=O)c2ccc(N)...  \n",
       "4e5w-4e5w_ligand_similar_44-CHEMBL1088346           n1c2c(nc3ccccc13)c1ccccc1n2CCN1C(CCCC1)C  \n",
       "...                                                                                      ...  \n",
       "3udh-3rsx_ligand_similar_32-CHEMBL528924                        Nc1cccc(c1)c1ccc2ccnc(N)c2c1  \n",
       "4crc-4cr9_ligand_similar_37-CHEMBL62083                                      Nc1nccc2ccccc12  \n",
       "3utu-1bcu_ligand_similar_99-CHEMBL62083                                      Nc1nccc2ccccc12  \n",
       "4gr0-3lka_ligand_similar_82-CHEMBL6648                          c1ccc2c(c1)c(ccc2)S(=O)(=O)N  \n",
       "2weg-2weg_ligand_similar_8-CHEMBL6648                           c1ccc2c(c1)c(ccc2)S(=O)(=O)N  \n",
       "\n",
       "[210 rows x 131 columns]"
      ]
     },
     "execution_count": 108,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "ids = data_random[\"chembl_id\"]\n",
    "data_random[ids.isin(ids[ids.duplicated()])].sort_values(\"chembl_id\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 110,
   "id": "fbbadb57-c9d3-4eaa-bac6-c1dcc71f4dba",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_random.to_csv(\"work/training/dual-model/data_random_with_smiles.tsv\", sep=\"\\t\", index=False, encoding=\"utf-8\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 111,
   "id": "b4aa9737-21d9-4789-8c22-6a3fd0b39d66",
   "metadata": {},
   "outputs": [],
   "source": [
    "data_random = pd.read_csv(\"work/training/dual-model/data_random_with_smiles.tsv\", sep=\"\\t\", encoding=\"utf-8\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 112,
   "id": "312e501d-bfd9-43c0-8d99-75de5bad2851",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(8421, 131)"
      ]
     },
     "execution_count": 112,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.shape"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 113,
   "id": "a4452162-58e4-47ca-b821-0b0033b0b530",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
       "      <th>chembl_id</th>\n",
       "      <th>tanimoto_index</th>\n",
       "      <th>WeightDescriptor</th>\n",
       "      <th>RuleOfFiveDescriptorV0</th>\n",
       "      <th>RuleOfFiveDescriptorV1</th>\n",
       "      <th>RuleOfFiveDescriptorV2</th>\n",
       "      <th>RuleOfFiveDescriptorV3</th>\n",
       "      <th>RuleOfFiveDescriptorV4</th>\n",
       "      <th>...</th>\n",
       "      <th>OtherSS</th>\n",
       "      <th>DominantSSHelix</th>\n",
       "      <th>DominantSSOther</th>\n",
       "      <th>BuriedASA</th>\n",
       "      <th>ExposedASA</th>\n",
       "      <th>RatioASA</th>\n",
       "      <th>PocketASA</th>\n",
       "      <th>volume</th>\n",
       "      <th>ba</th>\n",
       "      <th>smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_1</td>\n",
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       "      <td>0.720000</td>\n",
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       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-5.2</td>\n",
       "      <td>c1cccc(c1)/C=N\\\\O</td>\n",
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       "      <th>1</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_12</td>\n",
       "      <td>CHEMBL3188668</td>\n",
       "      <td>0.652174</td>\n",
       "      <td>208.2557</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
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       "      <td>0.6809</td>\n",
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       "      <th>2</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_18</td>\n",
       "      <td>CHEMBL3230486</td>\n",
       "      <td>0.650000</td>\n",
       "      <td>256.3418</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-6.3</td>\n",
       "      <td>c1ccc2c(c1)c1c(c(c2)C)c2c(cc1C)cccc2</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_24</td>\n",
       "      <td>CHEMBL286317</td>\n",
       "      <td>0.650000</td>\n",
       "      <td>306.4006</td>\n",
       "      <td>0</td>\n",
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       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-7.6</td>\n",
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       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_5</td>\n",
       "      <td>CHEMBL20936</td>\n",
       "      <td>0.692308</td>\n",
       "      <td>120.1521</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
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      "text/plain": [
       "    pdb             ligand_file      chembl_id  tanimoto_index  \\\n",
       "0  1owh   1c5z_ligand_similar_1   CHEMBL265435        0.720000   \n",
       "1  1owh  1c5z_ligand_similar_12  CHEMBL3188668        0.652174   \n",
       "2  1owh  1c5z_ligand_similar_18  CHEMBL3230486        0.650000   \n",
       "3  1owh  1c5z_ligand_similar_24   CHEMBL286317        0.650000   \n",
       "4  1owh   1c5z_ligand_similar_5    CHEMBL20936        0.692308   \n",
       "\n",
       "   WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "0          121.1368                       1                       0   \n",
       "1          208.2557                       1                       0   \n",
       "2          256.3418                       0                       1   \n",
       "3          306.4006                       0                       1   \n",
       "4          120.1521                       1                       0   \n",
       "\n",
       "   RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
       "0                       0                       0                       0   \n",
       "1                       0                       0                       0   \n",
       "2                       0                       0                       0   \n",
       "3                       0                       0                       0   \n",
       "4                       0                       0                       0   \n",
       "\n",
       "   ...  OtherSS  DominantSSHelix  DominantSSOther  BuriedASA  ExposedASA  \\\n",
       "0  ...   0.5265                0                1     0.6809      0.3191   \n",
       "1  ...   0.5265                0                1     0.6809      0.3191   \n",
       "2  ...   0.5265                0                1     0.6809      0.3191   \n",
       "3  ...   0.5265                0                1     0.6809      0.3191   \n",
       "4  ...   0.5265                0                1     0.6809      0.3191   \n",
       "\n",
       "   RatioASA  PocketASA  volume   ba  \\\n",
       "0    2.1333  1350.1025    1066 -5.2   \n",
       "1    2.1333  1350.1025    1066 -6.1   \n",
       "2    2.1333  1350.1025    1066 -6.3   \n",
       "3    2.1333  1350.1025    1066 -7.6   \n",
       "4    2.1333  1350.1025    1066 -4.7   \n",
       "\n",
       "                                       smiles  \n",
       "0                           c1cccc(c1)/C=N\\\\O  \n",
       "1                    OCc1c2c(cc3c1cccc3)cccc2  \n",
       "2        c1ccc2c(c1)c1c(c(c2)C)c2c(cc1C)cccc2  \n",
       "3  c12c(c(c3c(c1C)c1c(cc3)cccc1)C)ccc1c2cccc1  \n",
       "4                              N=C(N)c1ccccc1  \n",
       "\n",
       "[5 rows x 131 columns]"
      ]
     },
     "execution_count": 113,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 115,
   "id": "8ab8491b-662c-4eb0-a3a5-c491bdd08529",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "      <th>chembl_id</th>\n",
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       "      <th>WeightDescriptor</th>\n",
       "      <th>RuleOfFiveDescriptorV0</th>\n",
       "      <th>RuleOfFiveDescriptorV1</th>\n",
       "      <th>RuleOfFiveDescriptorV2</th>\n",
       "      <th>RuleOfFiveDescriptorV3</th>\n",
       "      <th>RuleOfFiveDescriptorV4</th>\n",
       "      <th>...</th>\n",
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       "      <th>RatioASA</th>\n",
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       "  <tbody>\n",
       "    <tr>\n",
       "      <th>8050</th>\n",
       "      <td>5a7b</td>\n",
       "      <td>5aba_ligand_similar_33</td>\n",
       "      <td>CHEMBL3481836</td>\n",
       "      <td>0.648936</td>\n",
       "      <td>338.8728</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
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       "      <td>0.5765</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.3</td>\n",
       "      <td>0.7</td>\n",
       "      <td>0.4286</td>\n",
       "      <td>1772.1041</td>\n",
       "      <td>644</td>\n",
       "      <td>-6.1</td>\n",
       "      <td>CC1(C)CN(CCC(=O)NCc2cccc(Cl)c2)CC[C@]1(C)O</td>\n",
       "    </tr>\n",
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       "<p>1 rows × 131 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "       pdb             ligand_file      chembl_id  tanimoto_index  \\\n",
       "8050  5a7b  5aba_ligand_similar_33  CHEMBL3481836        0.648936   \n",
       "\n",
       "      WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "8050          338.8728                       1                       0   \n",
       "\n",
       "      RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
       "8050                       0                       0                       0   \n",
       "\n",
       "      ...  OtherSS  DominantSSHelix  DominantSSOther  BuriedASA  ExposedASA  \\\n",
       "8050  ...   0.5765                0                1        0.3         0.7   \n",
       "\n",
       "      RatioASA  PocketASA  volume   ba  \\\n",
       "8050    0.4286  1772.1041     644 -6.1   \n",
       "\n",
       "                                          smiles  \n",
       "8050  CC1(C)CN(CCC(=O)NCc2cccc(Cl)c2)CC[C@]1(C)O  \n",
       "\n",
       "[1 rows x 131 columns]"
      ]
     },
     "execution_count": 115,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "data_random.iloc[[8050]]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 118,
   "id": "5078626c-73ef-42ae-bb0b-5fbddc05a4a4",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "8421"
      ]
     },
     "execution_count": 118,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "ms = [x for x in Chem.SmilesMolSupplier('work/training/dual-model/data_random_with_smiles.tsv', delimiter=\"\\t\", smilesColumn=130, nameColumn=2)]\n",
    "len(ms)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 119,
   "id": "c47fadff-48f3-467b-b743-a1d38171f69d",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": 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\n",
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       "<table><tr><td colspan=2 style=\"text-align:center\"><image 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ycnhcDj9+vVrbDug2wf06Ril2i48PnPmjKenJ93i5+fX9h4eetFNJzG6edGtChqX9C5SgUAQHh5eX1+vuV5wj9EYLSoiX3xBAMj69a3bFcdG2aV0d9alS5cUT0X0Z8vKqUgRE6MNDcTWllhYPBlrVhwbZVHbux5Wr14NAAsXLmS5MpZgjBJCSFNT08aNG+l1H5/Pp39mQ4cOjYuLU2opFot7PAWkoqKiovnz59P+FP2zB4BRo0adOnWqdwroEhOjTU3E2ZkYGBC6BlR7YpS0uTuL+ayj2bNnK/b0WcTEKCFk376nxpq1JEapzMzMV155hf706F/Nrl27WD8JsQJj9ImHDx+GhYWZm5vTYVCR4roSQgghycnJipP1mviEsS5duXLFw8NjyJAhRkZGmu4FPysmRgkhx48TAPLyy4RoWYxSdNRbKBROmDChk3FnVijGqFxOJk0iHA756y9CtCxGqeTk5GHDhtEuCGVjYxMQEBAeHh4bG3v16lXt+TxDzcEYfUpeXh4A2NvbK21X/PgGzd1u2E2//PILAAQHB7NYQ7sUY5QQMns2ASAJCdoYo1R5eXlVVZW23f2tGKOEkIwMwucTNzciFmtjjBJCrl69Sqdqvb29DQwM4GkCgcDT0zMsLOyrr746ceJEcXEx2/Wqn1Z/iQhb2n5dWmpqalJSkrGx8fLly1evXq25b1/oDloeHZnVZlFR8Oef8OmnEKOt34RN171pOXd3+OQT2LIFoqPZLqUD9Irezs6O5unDhw/T0tIyMzNv376dlpaWnZ19/fr169evM+3NzMzc3d3d3d3d3Ny8vb09PT0VO7O6CGO0W+bPn19UVPTuu+/qxB+elrCzg88+g1Wr4Ntv2S5Fx61bBwcPwuefw5gxbJfSDba2tra2tq++2vrFvWKxODc3lwnWK1eulJWVXbhwgX4WFGVjY+Pt7c0E64gRI7S/l6AIY7RbOBwOnYtEz2TZMti3D/74g+06dJyhIWzZAiEhkJzMdinPTiAQ0L4ns6WmpoZ2VGmwpqenl5SUHD169OjRo7QBn88fNmwYk6ru7u7MohTthDH6FKJ934He3Nxsa2trYGDw8OFDukULi+wInw/ffQeTJ4N2f6GnDggOhhkzICmJ7TrUwdzcfMKECcxHT0il0vv37ysGa3Z2dmZmZmZmJm3A4XCqq6vNzMzYK7kLGKPaTi6X19TU0G/H00UTJ8Kbb8KBA2zXoft27IC//gLt+75RVc/rPB7P0dHR0dGRGQeoq6vLyMi4devWzZs3MzIy6urqtDlDAWMUqVF0NOzcCaamytt/+AF27oQ2U7ioff36wb17YGSkvN3ZGe7dg+ZmsLNjo6xeZGpq6u/vz9yYq/20+nvqkW7ZtQvWrGlne2MjrFkDP/7Y2/XoKC4XHB3B2rr14fjx4OMDYjEAgK0tODoCDzs/WgZjFKlNXBzs3g0ymfL2R49g9244coSNmnRfWhqkpbFdBOoUxuhTdGL2RieKRH0HviExRrUdvkcR0nIYowghpBKMUYQQUgnO+T1FJ66gtbzI4cOVt7SddELdR+9c0NbfNgLAGEVqN2aM8t98UxPcv89SNUjztPy83gswRpGa7d8Pjz/5ulVRERw+zFI1CGkejo1qOzzVI6TlMEYRQkglGKNP0Ymun04UifoOfEPi2ChCWm3w4OFSqRTgDv61ai38xSC1sbOD+vp2lubweODkBLa2bNSk+x48yJNKpX24q6cDMEa1nQ5dMXU0HT9wINy927ulINSLcGz0KTqRWTpRJEJqIZFItm3bxnYVXcAYRUiraf9ZU+0VNjU1Mf/m8/kbN24sLy9X1841AWMUIaRFSktLHRwcFLe4u7tnZGSwVU93YIwihNiUn5+/ceNG5uHAgQOlUmlFRQWzxcPD49atW2yU1l0Yo9rO0NDw6tWrZ8+eZbsQhNSjsbGxoKCAeSgQCHbu3KnYQKn7iTGqYzoZ5UlKSpKx8VFFenp63t7enp6ezBbtHyxDaqT9v+5nrfDs2bOLFi1iHg4aNEgikXTS/cQYfU6cPHkyMDDQx8cHe4UIPasjR45s376dedg2FpW6nyNHjlRsMHLkyH79+vVCnT2GMdotUql06NCh169fnzx58ty5cwsLC9muCCHtlZ2dfefOHeahnp7eiRMnmIeDBw/mcrm1tbXMloULFyoG5dy5c9evX8887NevX3JysoZLVgnG6FP09PTMzMxKSkqSkpIUt0+bNi0rK2vTpk0mJibx8fGurq6rVq1qaGjo/Qrr6uoOHjxoZGRkaGjY+0dHbElJSWG7hA5dunQJAKRSKbMlJSUlNTWVeThu3Lhly5YpvqS4uNjMzIx5uGDBAm9vb+ahubm5jY2NBitWO4KeFhUVRX8y06dPz87OVnq2uLg4LCyMDgMNGjQoNjZWLpf3TmEymSwmJmbAgAH00GKxuHeOi9iVlJTE4XA4HM78+fOLiorYLucpOTk5ISEhAKCnp2dkZPTo0SO2K2IHxqgysVgcHR1taWkJAHw+f9GiRRUVFUptUlNTx40bR9PW19f34sWLmq4qJSXFz8+PHnHMmDGXLl3S9BGRlmhsbIyMjDQwMAAAQ0PDyMjIpqYmtosiNTU1ERER+vr6AGBsbGxnZwcAP/30E9t1sQNjtH1VVVXh4eF6enoAYGFhERUVJZVKFRvI5fLY2NiBAwcCAIfDCQsLKykp0UQlDx48YPq/gwcP7s3+L9Iebd8GbFUik8liY2Otra0BgMvlhoWFlZaW7tmzBwBeeeUVtqpiF8ZoZ65duzZ58mTaB/T09Pz777+VGjx69CgyMpKek42MjCIjI5ubm9V1dNoNEQqFtBsSERHR0NCgrp0jXXT69OnRo0fTN+SUKVOuX7/OYgGTJ0++du0a3V5dXa2vr8/lcrVt2KF3YIx2LTExkbk7bebMmXl5eUoNcnNz6QgRADg7O8fHx6t4RLlcHh8fP3ToUNrVDQkJKSgoUHGf6PlAO4N0iJx2BsvKynrhuPfv3+/8qmjWrFkAsHXr1l4oRttgjHaLSCSi0/QAIBQKIyIi6uvrldqcOnXKw8ODhulLL7108+bNnh3rypUr/v7+dD/e3t7nzp1TuXz0vKFDkwKBAADMzMw2bdrU0tKioWO1HZwViURtmyUkJNCLNg2Voc0wRp+B4jS9ra1t2xOyRCJhpqd4PF6701Od73/RokVcLhcAbGxsoqOjZTKZuv8T6Plx586dwMBAesZ1cXE5evSoevdPr4qGDBnSnauilpaW/v37A0CPOxC6C2P0mXU5TV9RUfH+++/T6SlLS8vLly93uc+WlpaoqCi6AlkgEISHh9fV1WmmfPS8SU5OdnNzo2/IgICA27dvq2W3qamp48ePp7v18fE5f/58ly95//33AWDlypVqKUCHYIz2RHem6bOysqZNmzZo0KAuF9MlJiY6OjoyY6/37t3TWOHo+SQWi6OiokxNTekqvfDw8Nra2h7vTfGqyNbWtvtXRRcuXKAvUVrW8tzDGO05Ok1Px4w6mqZ/8OBBJ3vIzMx85ZVXaIC6uroeP35ck/Wi51xlZSWzSq9///5tV+l1SXEOgF4VtZ0D6JyLiwsAnDx58plepeswRlXVs2n6LtelItQzaWlpEydOpG/IF1544ezZs918YZcrUrojMjISADZ//HEPXqu7MEbVo/vT9PT6i95Q3NFdUgipKDEx0d7ensnE/Pz8Thqnp6dPmjSJWR995syZHh+39N69pmHDiLEx6Us3hmKMqg2dpreysupkmj45Odnd3Z2ZDcjIyGClVNQXNDY2btq0ydjYuJPbN1QfB2jHuHEEgBw4oOp+dAfGqJrRq3Uej8dcrUskEkLInTt3Zs6cyaxNOXLkCNuVoj6ho5uJ1Tsr9ZTduwkAmTZNPXvTBRijGnHjxo0XX3yRhubIkSODg4P5fD5dKb1t2zb8cCbUyxQ/2sbPz2/nzp2Ka6TUfFVUVUX09YmeHtHMp0xoIYxRDWJWMllaWvbmfXsItSWVSplBJzo07+rqeuLECY0c7I03CADZtk0jO9c+HEIIII1pbm7ev3+/k5OTpaXlqFGj2C4H9XW1tbUbN2709fUtKSn54IMP6OiT+iUkQFAQeHlBerpG9q9lMEYRQuomFoOtLVRVwc2b8HgFy3MMv0QEIaRuAgEEBQEAHDjAdim9AXujCCENOH8eJk6EQYOgsBD09NiuRrOwN4oQ0gB/f3B0hOJi6APfSY4xihDSAA4H5s8HLhcuX2a7FI3Di3qEkGaUl0NLC9jZsV2HxmFvFCGkGQMGQH4+hIXBiBFgZQXDhsGsWXDwIDBdt4sXwc8Pdu9u57WbNoGfH9y61Zv19hjGKEJIAwiBJUtg8mT4/Xewt4fZs8HDA86cgTlzYOZMEIkAAGprITUV7t9v5+X5+ZCaCg0NvVx1z2hm8S1CqI/btQt27AA/P/j9dxg0qHVjXR28/TYcOgTh4fD996zWp07YG0UIqVtTE6xfD8bGkJDwJEMBwNQUfv4ZnJzghx8gN5e9+tQMYxQhpG5nzkBlJcyaBba2yk8JhfDeeyCXQ0ICG5VpBF7UI4TU7do1AIDHnymlbOzY1jb0PtHmZqiuVm7T0qK56tQOYxQhpG5VVQAAlpbtPztgwJM2ALBjB+zY0StlaQrGKEJI3egHR8nl7T8rkz1pAwAvvQQzZii3+e03SEnRUHVqhzGKEFI3KysAgJKS9p99+BAAwNq69aGvLyxfrtwmJ0eHYhSnmBBC6ubrCwBw/nz7z54796TNcwFjFCGkbhMmwJAhcOwY5OQoP1VXB3v3gr4+PP5a8ucAxihCSN309GDzZhCL4dVXISPjyfbiYnj9dSgpgYiI1omm5wKOjSKENCA0FIqKYPVqGD0avLzA3h7KyiA1FcRieP99+PxztutTJ4xRhJBmfPopBAbC3r2QkgIZGWBuDu+8A2Fh4O/f2sDWFubOhdGj23mtry/U1XW4ZErL4AflIYSQSnBsFCGEVIIxihBCKsEYRQghlWCMIoSQSjBGEUJIJRijfdr58+dfffVVKysrPp/v5OT02WefiUSibdu2ubi4KLX86aef7O3ta2trV61aZf80Hx8f2iYwMNDJyenq1auKL2xqanJzc3NychKJRACwatUqp8f8/f2XLFlSXFwMAHv37rW3txeLxUrHzc/PDw0NtbKyMjExGTt2bGJiYtv/xcKFC52cnMaNG8dsOXTo0JgxY4yNja2trWfPnp2jcC/NuXPnZs2a5eTkVFBQwGz8448/mPZBQUG5jz9RuKGhYenSpXZ2dkKh0M3NbceOHczKlqampnXr1g0fPlxfX9/GxmbBggUtOvXZbkiNcN1o3xUfH//mm296eXl9+eWXgwYNunHjxtdff11eXj5gwADFiKHq6+sLCwtlMlllZaVIJNq8eTPzlFAopP+4ePFibW3tL7/8wgQrABw9ejQrKwsACgsLXV1d6cu/+eYbsVhcUFCwe/fuo0ePXrt2ra6urrCwUGn5XWlp6dixY319fb///nsejxcdHT179uzTp09PnDiRaXP48OEff/xx/PjxeXl5dMuZM2eCgoIWLFjwzTff1NfXr1y58uWXX87MzKyurg4KCrpx44azs3NeXh6NdQA4ffp0cHDw22+/TduvWLGCthcIBC+//HJzc/PmzZv79+9/4sSJJUuWEEKWLFkik8lee+21y5cvL1261MfHp7m5uaioSF9fX12/GqRjCOqTGhoazMzMPD09m5ubmY05OTm1tbVr1qzh8/lK7b/99lsAqKysXLhwoaOjY9sd1tTUAICHh8fgwYNlMhmzPTg42MPDAwCOHTtGCFm4cKGzszPzbFJSEgAkJSVt3boVABSLIYQUFxd//vnnzN6ampoEAsGyZcuYBnV1dYMHD/7oo4+WLl1qa2tLNy5dulQgEIjFYvrw6NGjAHD69OmWlpa4uLi6ujq65fbt27TBJ598oq+vL5FI6MPDhw8DwN9//y0SidauXVtRUcEczsfHZ8KECYSQH374AQASEhK6/kGjPgAv6vuopEp820YAAAc/SURBVKSk2tra//u//1PsQw0bNszU1LRnO8zPzweAiIiIoqKi848/2qehoeHYsWNLly7l8Xhte7gAYGBgAADNzc3t7tPW1nbdunVcbuu7tK6uTiKRKFa4cuVKqVT673//W2mfEonk7t279GFVVRUAWFhYCASCOXPm9OvXr20N7bYXCoWRkZGWj2+kkcvl1dXV9Og///yzi4vLG2+80c0fDnq+4UV9H3Xjxg0A8Ovgax4IIampqYpbCgsLmX+LRCLai6Q8PDzs7OxojE6dOtXT0zMuLm7SpEkAcPjwYalU+sYbb6xfv56J0ZaWlrS0NEJIQUHB2rVrR40aNW3atD179nRUqkwmy83NzcnJ+fLLL4cPH7548WK6/ezZszExMXFxcWZmZortFy5cGB0dPW7cuGXLlo0fP37FihXh4eGjRo3qaP/vvvtuTEzM2LFjly9fPnbs2IiIiCVLlowcOZJpUFBQkJeXFxMTU1NTs27dOgC4du3aSy+99Oeff/7+++9FRUVeXl7Lly/v379/R4dAzzm2u8OIHR999BEAMFe+itasWdPRu4Ve1AMAT8F//vMfQsjWrVuFQqFcLt+wYYOVlRW9Rp45c2ZgYCAh5MUXXwwODiaE0JczhELhzz//TF8ObS7qqYqKCtoHNDAw2L9/P93Y3Nzs6uo6bdo0+lDxol4ul3/66acGBgb0VXZ2djS1GUoX9XK5fPny5UKhkLYfMmRIenq6YvvRo0dzOBwAWL16tUQikcvlenp65ubmjo6OixcvDg8PNzMzc3Fxqa+v7/GvA+k0vKjvowwNDeHxBWxbfD6/+Wk7FL4tx9HRUaLg3XffBYCCggJ7e3sOhxMSElJRUXHq1Kna2trk5OTg4GAAcHBwYHqjDg4O1dXV1dXV9+/fX7Nmzbx586Kjozsp1dLSsra2trGx8auvvlqwYMHevXsBYN26dYWFhXTEVsmGDRv27Nlz/vz5srKygwcP9uvXz9/fP6Xjj1Jfv379d999d+HChdLS0vj4eBMTE39/f8XO+PXr11taWo4fP75r164PP/yQw+EYGBj4+fndvn179+7dO3bsSExMzMnJOXDgQCf/C/Qcwxjto0aMGAEAOW0/Vfcx/afxeF2M/+Tn59vb2wOAi4uLh4dHXFxcQkKCXC5/7bXXAMDe3p5e9QMA7cqZm5vb2dn961//GjNmDJ2x6ZyhoeHHH3/s6+u7d+/evLy8LVu2WFhYrFq1as6cOXPmzDl27FhNTc2cOXNyc3O3b98eEhLi7e2tr68fHByckpIiFAo7GTTYvn373Llzvby8DAwMQkJCUlJS9PX1ldrz+fxp06YtWLAgNjZWJpPZ2tqamJjQgV0A8Pf35/F4d+7c6fJ/gZ5LGKN91PTp0/l8/u7du9W1w4KCAgcHB/rv4ODgP/74Y//+/VOnTrWwsAAABweHqqqq+vr6ti+sr6/vZF7rIf3ense4XG5LSwsh5J133pkxY4b5Y/r6+hwOx9zcXE9PjxCip6fHvMTIyEggEHQ0i0Uvyjpqr3R0PT09qVQqk8nc3d3Pnz8vkUjo9nv37kmlUjs7u05/Qui5hVNMfdTAgQP/9a9/rVu3zsTEZMWKFUOGDHnw4MGhQ4fGjx/f5WvFYvE1+kXkj3l4eBQUFLz11lv04dy5cyMjI8+cOUMvwAGAJiydp5JIJHSNZ3V19b59+7KyslasWEHXS924cYPP5zO7raysfO2117Zv3z5//nxCyN69ey9fvrx+/XonJyelcYBly5ZVVVXRjQEBAT///POsWbNmzJghkUi++OKLsrKyoKAgACgtLRWJRKWlpQBQVFRkYGBgbW0dEBBw4MCBN954Y/r06RKJZMOGDeXl5UFBQaWlpS4uLv/85z8jIiJMTU2Tk5P/+9//zpgxQyAQfPDBB4cOHVq8ePHq1atFItF7771namoaGhra418H0m0sjssidsnl8m3btlkqfDKuvb39H3/80eW60bbvoszMTAA4ePAg097d3Z3H4zGLLouKigDg8OHDSi8fMmQIvTWITjEpqa+vX79+vZGREX3I5/M//PBDZoGnIsUppsrKyjfffJPL5RoYGPD5fGNj46+//po+RUcYFCUkJFRWVoaGhtL2PB7PxMRk69attH1cXJyNjQ1tyeFwZsyYwfyPvv32WxMTE/qUk5PTuXPn1PaLQboGP7a5r5PJZDk5OU1NTTY2NgMHDuRwOI8ePWpsbLRmvv8WAACamprq6uqsra0bGhqY+38Y/fv3f/TokYmJCTOE2tjYKJVKmat1Qkhtba2RkZFUKmVumjQwMGDugBKJRG0v+a2trTkcTlNTU3Z2tlgsdnV1bbvqkylPLBYrDg7U1NTk5+dzOBxXV1dmEPPRo0fMlThlbGxM+781NTV5eXl6enojRoxg2tOfT3Z2dn19vb29PROpVHNzc25urkAgcHFxoVP5qG/CGEUIIZXgFBNCCKkEYxQhhFTy/wEy4sZArLNEAAABsHpUWHRyZGtpdFBLTCByZGtpdCAyMDIyLjAzLjQAAHice79v7T0GIOBlgABGIBYHYgkgbmBkY0gAiTGzMSgAaRYEF0QzMbGDheFcBK0BEmbhgNBAZRlgmhGuwAGigM0BLMHMiI0BUSIItgJJHN0uBRUQDXcaB4Rm5Ab6hJEJKAA0g4GFlYGVjYGNnYGdQ4OJnVOBk4uBi5uBmyeDiYc3gZcvg4mPP4FfgIFfMIOJRYhBSJhBWIRBRJSFSUSMQYSRQZA7QYSJjVFEWIiFmY2Hl49fkFtcjhESVGAgzto81aFMfJoNiBPFlONwK8LVDsTm+N3gEPdygj2IHTPHxKGz1hDMbgv6ZX/ruBtYTXdbt73nTYj4KaZUu1tmHmBx53CV/ZymRmDxK0oq+1ukboLZlwUP7r+11BOs5vk78QMnJ0DUMCb5H7gl4g0Wl8n3P/DU3Xc/iC1d2Hxgd+cyMFtSZf4B1Tc+YHa37PwDt5p9wOq7Luw64OlhDDbnf3Lzgc43EDP9LX7Zc/r5gdWrNpk4rLNaDmbbfc12OLUSIr6vfqqDdq4SmL37aYPDhWX3wWwxAJ5qaADezjpoAAACDHpUWHRNT0wgcmRraXQgMjAyMi4wMy40AAB4nH1USY4bMQy8+xX6QAvctB1yGC+ZBIltIPHkDwHmOP9HSHXL0gDqdFuERJRLpKvo07fL9fiTJWPmeHD2/Dr/+Pvhng+dD5qH/3xKKe4PA8Dh6mzjjpfX7zd3erwcW+Z0f7s9fjtiR6Lf0fcz9uVxv7YMupMTHxORKNaDVkZkm/r0b5Li2MecYsVhoTTFceUDhijs0CMTTnGiOPKZCBQHPhae3xvcTWlKCLHisMicLyofeijQ+GReX1IceCJufCFMcVlxi/KIImIljPOLi7tvQFQg7gMRtJUFfYDMlRJLLHOkibKQ58Tt8jSvEk2WhT0JcEiVc0c/5IasdWrFWbVOeQY1bRbxCCkoqZbMoPspNKzQkhgNaqwgc2hsUGrtl7lEqBq9uyX4zGntPwHsdJVbqaHU/mPJO79pqQYpQbIKXwsN8/YJNmuCGNK6j/OWCLehiE/ORHMkbWOGGzKy7HCy+kkHiDKstyfZ4bzczp8meZ3t4/127rNtL/UR1oPjPql2lD6QqCv0uUNdsY8X6kp9ilBX7sNCukofCdQjjs7HGnBwONZAg5PFAvLgWLGAMhhTLGAY/GdHNddgM6whDXaSmsmDa6w5LIM50AKNJkALhIPYaMGk/Pr6hQdp1zwPEq6ZZ6LWnYduTbtRKTu3f3DdH/4BegYlBRs+GV4AAAENelRYdFNNSUxFUyByZGtpdCAyMDIyLjAzLjQAAHicRZE9bgQhDEavknJGmrX8h220ihTJ/e4BolTb5gg5fAzMJHQ8nj+DyaQt93xsmbm9P/dHvvhVa8vv/cV75md+fA3l+fazKZgz64GAFMLkx13Awm0g6lyHx10BBYsQUCkFGIIZh2JdZCgEvbWzSGkR7Hg6OmMQmMVUptTaQLc61drY1Iz+GRWjxQoRNAyxWWl9Wgzi0lehrzABVjytkD9EZEeFRr3Qo5gCoVd8pQoSLtRdLg3VL8ZnWp8PuDUI8dnTEVeDEdbOa0S/RqGhK6vNlmNeqLo6msYasl2S85DGV9BCJqoLIQfOOq8ZxrH//AIl1GFj3GeyowAAAABJRU5ErkJggg==\"></td></tr>\n",
       "<tr><th style=\"text-align:right\">pdb</th><td style=\"text-align:left\">5a7b</td></tr>\n",
       "<tr><th style=\"text-align:right\">ligand_file</th><td style=\"text-align:left\">5aba_ligand_similar_33</td></tr>\n",
       "<tr><th style=\"text-align:right\">tanimoto_index</th><td style=\"text-align:left\">0.648936</td></tr>\n",
       "<tr><th style=\"text-align:right\">WeightDescriptor</th><td style=\"text-align:left\">338.8728</td></tr>\n",
       "<tr><th style=\"text-align:right\">RuleOfFiveDescriptorV0</th><td style=\"text-align:left\">1</td></tr>\n",
       "<tr><th style=\"text-align:right\">RuleOfFiveDescriptorV1</th><td style=\"text-align:left\">0</td></tr>\n",
       "<tr><th style=\"text-align:right\">RuleOfFiveDescriptorV2</th><td style=\"text-align:left\">0</td></tr>\n",
       "<tr><th style=\"text-align:right\">RuleOfFiveDescriptorV3</th><td style=\"text-align:left\">0</td></tr>\n",
       "<tr><th style=\"text-align:right\">RuleOfFiveDescriptorV4</th><td style=\"text-align:left\">0</td></tr>\n",
       "<tr><th style=\"text-align:right\">RuleOfFiveDescriptorV5</th><td style=\"text-align:left\">0</td></tr>\n",
       "<tr><td colspan=2 style=\"text-align:center\">Property list truncated.<br />Increase IPythonConsole.ipython_maxProperties (or set it to -1) to see more properties.</td></tr></table>"
      ],
      "text/plain": [
       "<rdkit.Chem.rdchem.Mol at 0x7fe5f969f460>"
      ]
     },
     "execution_count": 119,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "ms[8050]\n"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 120,
   "id": "3752aa75-af97-4fc5-8aad-a7d4de6df305",
   "metadata": {},
   "outputs": [],
   "source": [
    "fps = [rdMolDescriptors.GetMorganFingerprintAsBitVect(m,2,2048) for m in ms]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 121,
   "id": "86a07c95-4c1b-4147-b086-67964a50f76b",
   "metadata": {},
   "outputs": [],
   "source": [
    "lp = rdSimDivPickers.LeaderPicker()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 122,
   "id": "deb50c12-6b1a-4751-914d-81d681ab877f",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "1684\n"
     ]
    }
   ],
   "source": [
    "thresh = 0.59 # <- minimum distance between cluster centroids\n",
    "picks = lp.LazyBitVectorPick(fps,len(fps),thresh,int(len(fps)*0.2))\n",
    "print(len(picks))"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 123,
   "id": "784aad25-8dc1-403b-b6a9-436b07767a6c",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "[0.41,\n",
       " 0.41,\n",
       " 0.4098360655737705,\n",
       " 0.4098360655737705,\n",
       " 0.4098360655737705,\n",
       " 0.4098360655737705,\n",
       " 0.4098360655737705,\n",
       " 0.4098360655737705,\n",
       " 0.4098360655737705,\n",
       " 0.4098360655737705]"
      ]
     },
     "execution_count": 123,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "from rdkit import DataStructs\n",
    "pickfps = [fps[x] for x in picks]\n",
    "nearest = []\n",
    "simhist = []\n",
    "for i,fpi in enumerate(pickfps):\n",
    "    tfps = pickfps[:]\n",
    "    del tfps[i]\n",
    "    sims = DataStructs.BulkTanimotoSimilarity(fpi,tfps)\n",
    "    nearest.append(max(sims))\n",
    "    simhist.extend(sims)\n",
    "sorted(nearest,reverse=True)[:10]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 124,
   "id": "1c14935c-bc32-4a73-8d78-44aadcf1f7b9",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": "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\n",
      "text/plain": [
       "<Figure size 432x288 with 1 Axes>"
      ]
     },
     "metadata": {
      "needs_background": "light"
     },
     "output_type": "display_data"
    }
   ],
   "source": [
    "hist(simhist,bins=20);\n",
    "xlabel('similarity');"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 127,
   "id": "2242186e-f195-4265-905b-26fa688d7046",
   "metadata": {},
   "outputs": [],
   "source": [
    "test_ligand_diversity = data_random.iloc[picks]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 128,
   "id": "9bf07e43-7471-445d-b5a2-77dd5b886653",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(1684, 131)"
      ]
     },
     "execution_count": 128,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "test_ligand_diversity.shape"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 133,
   "id": "93211a88-b917-4ffe-9ecd-340d98ac1212",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
       "      <th>chembl_id</th>\n",
       "      <th>tanimoto_index</th>\n",
       "      <th>WeightDescriptor</th>\n",
       "      <th>RuleOfFiveDescriptorV0</th>\n",
       "      <th>RuleOfFiveDescriptorV1</th>\n",
       "      <th>RuleOfFiveDescriptorV2</th>\n",
       "      <th>RuleOfFiveDescriptorV3</th>\n",
       "      <th>RuleOfFiveDescriptorV4</th>\n",
       "      <th>...</th>\n",
       "      <th>OtherSS</th>\n",
       "      <th>DominantSSHelix</th>\n",
       "      <th>DominantSSOther</th>\n",
       "      <th>BuriedASA</th>\n",
       "      <th>ExposedASA</th>\n",
       "      <th>RatioASA</th>\n",
       "      <th>PocketASA</th>\n",
       "      <th>volume</th>\n",
       "      <th>ba</th>\n",
       "      <th>smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_1</td>\n",
       "      <td>CHEMBL265435</td>\n",
       "      <td>0.720000</td>\n",
       "      <td>121.1368</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-5.2</td>\n",
       "      <td>c1cccc(c1)/C=N\\\\O</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_12</td>\n",
       "      <td>CHEMBL3188668</td>\n",
       "      <td>0.652174</td>\n",
       "      <td>208.2557</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-6.1</td>\n",
       "      <td>OCc1c2c(cc3c1cccc3)cccc2</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_18</td>\n",
       "      <td>CHEMBL3230486</td>\n",
       "      <td>0.650000</td>\n",
       "      <td>256.3418</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-6.3</td>\n",
       "      <td>c1ccc2c(c1)c1c(c(c2)C)c2c(cc1C)cccc2</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_5</td>\n",
       "      <td>CHEMBL20936</td>\n",
       "      <td>0.692308</td>\n",
       "      <td>120.1521</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-4.7</td>\n",
       "      <td>N=C(N)c1ccccc1</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>5</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_6</td>\n",
       "      <td>CHEMBL31561</td>\n",
       "      <td>0.684211</td>\n",
       "      <td>106.1653</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-4.5</td>\n",
       "      <td>c1(ccc(cc1)C)C</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>5 rows × 131 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "    pdb             ligand_file      chembl_id  tanimoto_index  \\\n",
       "0  1owh   1c5z_ligand_similar_1   CHEMBL265435        0.720000   \n",
       "1  1owh  1c5z_ligand_similar_12  CHEMBL3188668        0.652174   \n",
       "2  1owh  1c5z_ligand_similar_18  CHEMBL3230486        0.650000   \n",
       "4  1owh   1c5z_ligand_similar_5    CHEMBL20936        0.692308   \n",
       "5  1owh   1c5z_ligand_similar_6    CHEMBL31561        0.684211   \n",
       "\n",
       "   WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "0          121.1368                       1                       0   \n",
       "1          208.2557                       1                       0   \n",
       "2          256.3418                       0                       1   \n",
       "4          120.1521                       1                       0   \n",
       "5          106.1653                       1                       0   \n",
       "\n",
       "   RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
       "0                       0                       0                       0   \n",
       "1                       0                       0                       0   \n",
       "2                       0                       0                       0   \n",
       "4                       0                       0                       0   \n",
       "5                       0                       0                       0   \n",
       "\n",
       "   ...  OtherSS  DominantSSHelix  DominantSSOther  BuriedASA  ExposedASA  \\\n",
       "0  ...   0.5265                0                1     0.6809      0.3191   \n",
       "1  ...   0.5265                0                1     0.6809      0.3191   \n",
       "2  ...   0.5265                0                1     0.6809      0.3191   \n",
       "4  ...   0.5265                0                1     0.6809      0.3191   \n",
       "5  ...   0.5265                0                1     0.6809      0.3191   \n",
       "\n",
       "   RatioASA  PocketASA  volume   ba                                smiles  \n",
       "0    2.1333  1350.1025    1066 -5.2                     c1cccc(c1)/C=N\\\\O  \n",
       "1    2.1333  1350.1025    1066 -6.1              OCc1c2c(cc3c1cccc3)cccc2  \n",
       "2    2.1333  1350.1025    1066 -6.3  c1ccc2c(c1)c1c(c(c2)C)c2c(cc1C)cccc2  \n",
       "4    2.1333  1350.1025    1066 -4.7                        N=C(N)c1ccccc1  \n",
       "5    2.1333  1350.1025    1066 -4.5                        c1(ccc(cc1)C)C  \n",
       "\n",
       "[5 rows x 131 columns]"
      ]
     },
     "execution_count": 133,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "test_ligand_diversity.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 130,
   "id": "705b33cd-240a-48ab-a7ca-314e77c4c173",
   "metadata": {},
   "outputs": [],
   "source": [
    "train_ligand_diversity = data_random.drop(picks)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 132,
   "id": "9b4ebbba-2128-476c-8eea-d2e2377d1c90",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(6737, 131)"
      ]
     },
     "execution_count": 132,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "train_ligand_diversity.shape"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 134,
   "id": "c25ac723-62dc-4213-b5be-bc6dc003fc74",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
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       "        vertical-align: middle;\n",
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       "\n",
       "    .dataframe tbody tr th {\n",
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       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>pdb</th>\n",
       "      <th>ligand_file</th>\n",
       "      <th>chembl_id</th>\n",
       "      <th>tanimoto_index</th>\n",
       "      <th>WeightDescriptor</th>\n",
       "      <th>RuleOfFiveDescriptorV0</th>\n",
       "      <th>RuleOfFiveDescriptorV1</th>\n",
       "      <th>RuleOfFiveDescriptorV2</th>\n",
       "      <th>RuleOfFiveDescriptorV3</th>\n",
       "      <th>RuleOfFiveDescriptorV4</th>\n",
       "      <th>...</th>\n",
       "      <th>OtherSS</th>\n",
       "      <th>DominantSSHelix</th>\n",
       "      <th>DominantSSOther</th>\n",
       "      <th>BuriedASA</th>\n",
       "      <th>ExposedASA</th>\n",
       "      <th>RatioASA</th>\n",
       "      <th>PocketASA</th>\n",
       "      <th>volume</th>\n",
       "      <th>ba</th>\n",
       "      <th>smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1c5z_ligand_similar_24</td>\n",
       "      <td>CHEMBL286317</td>\n",
       "      <td>0.650000</td>\n",
       "      <td>306.4006</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-7.6</td>\n",
       "      <td>c12c(c(c3c(c1C)c1c(cc3)cccc1)C)ccc1c2cccc1</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>11</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1owh_ligand_similar_1031</td>\n",
       "      <td>CHEMBL1580702</td>\n",
       "      <td>0.626667</td>\n",
       "      <td>348.3528</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-8.0</td>\n",
       "      <td>O=C(Nc1cc(O)ccc1)c1cc(C(=O)Nc2cc(O)ccc2)ccc1</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>15</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1owh_ligand_similar_1040</td>\n",
       "      <td>CHEMBL1213773</td>\n",
       "      <td>0.626667</td>\n",
       "      <td>241.2857</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-6.4</td>\n",
       "      <td>C(=O)(Nc1ccc(cc1)OC)c1cc(ccc1)C</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>17</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1owh_ligand_similar_1048</td>\n",
       "      <td>CHEMBL1548673</td>\n",
       "      <td>0.626506</td>\n",
       "      <td>324.3313</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-6.9</td>\n",
       "      <td>O=C(Nc1c(C(=O)O)cccc1)c1ccc(NC(=O)C2CC2)cc1</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>19</th>\n",
       "      <td>1owh</td>\n",
       "      <td>1owh_ligand_similar_106</td>\n",
       "      <td>CHEMBL1724652</td>\n",
       "      <td>0.680556</td>\n",
       "      <td>292.2894</td>\n",
       "      <td>1</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>0</td>\n",
       "      <td>...</td>\n",
       "      <td>0.5265</td>\n",
       "      <td>0</td>\n",
       "      <td>1</td>\n",
       "      <td>0.6809</td>\n",
       "      <td>0.3191</td>\n",
       "      <td>2.1333</td>\n",
       "      <td>1350.1025</td>\n",
       "      <td>1066</td>\n",
       "      <td>-7.2</td>\n",
       "      <td>O=C(Nc1c2c(ccc1)cccc2)c1ccc([N+](=O)[O-])cc1</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>5 rows × 131 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "     pdb               ligand_file      chembl_id  tanimoto_index  \\\n",
       "3   1owh    1c5z_ligand_similar_24   CHEMBL286317        0.650000   \n",
       "11  1owh  1owh_ligand_similar_1031  CHEMBL1580702        0.626667   \n",
       "15  1owh  1owh_ligand_similar_1040  CHEMBL1213773        0.626667   \n",
       "17  1owh  1owh_ligand_similar_1048  CHEMBL1548673        0.626506   \n",
       "19  1owh   1owh_ligand_similar_106  CHEMBL1724652        0.680556   \n",
       "\n",
       "    WeightDescriptor  RuleOfFiveDescriptorV0  RuleOfFiveDescriptorV1  \\\n",
       "3           306.4006                       0                       1   \n",
       "11          348.3528                       1                       0   \n",
       "15          241.2857                       1                       0   \n",
       "17          324.3313                       1                       0   \n",
       "19          292.2894                       1                       0   \n",
       "\n",
       "    RuleOfFiveDescriptorV2  RuleOfFiveDescriptorV3  RuleOfFiveDescriptorV4  \\\n",
       "3                        0                       0                       0   \n",
       "11                       0                       0                       0   \n",
       "15                       0                       0                       0   \n",
       "17                       0                       0                       0   \n",
       "19                       0                       0                       0   \n",
       "\n",
       "    ...  OtherSS  DominantSSHelix  DominantSSOther  BuriedASA  ExposedASA  \\\n",
       "3   ...   0.5265                0                1     0.6809      0.3191   \n",
       "11  ...   0.5265                0                1     0.6809      0.3191   \n",
       "15  ...   0.5265                0                1     0.6809      0.3191   \n",
       "17  ...   0.5265                0                1     0.6809      0.3191   \n",
       "19  ...   0.5265                0                1     0.6809      0.3191   \n",
       "\n",
       "    RatioASA  PocketASA  volume   ba  \\\n",
       "3     2.1333  1350.1025    1066 -7.6   \n",
       "11    2.1333  1350.1025    1066 -8.0   \n",
       "15    2.1333  1350.1025    1066 -6.4   \n",
       "17    2.1333  1350.1025    1066 -6.9   \n",
       "19    2.1333  1350.1025    1066 -7.2   \n",
       "\n",
       "                                          smiles  \n",
       "3     c12c(c(c3c(c1C)c1c(cc3)cccc1)C)ccc1c2cccc1  \n",
       "11  O=C(Nc1cc(O)ccc1)c1cc(C(=O)Nc2cc(O)ccc2)ccc1  \n",
       "15               C(=O)(Nc1ccc(cc1)OC)c1cc(ccc1)C  \n",
       "17   O=C(Nc1c(C(=O)O)cccc1)c1ccc(NC(=O)C2CC2)cc1  \n",
       "19  O=C(Nc1c2c(ccc1)cccc2)c1ccc([N+](=O)[O-])cc1  \n",
       "\n",
       "[5 rows x 131 columns]"
      ]
     },
     "execution_count": 134,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "train_ligand_diversity.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 140,
   "id": "f9c67090-c4da-4ac1-aab4-94eef5245b02",
   "metadata": {},
   "outputs": [],
   "source": [
    "train_ligand_diversity_meta = train_ligand_diversity[[\"pdb\", \"ligand_file\", \"chembl_id\", \"tanimoto_index\", \"smiles\"]]\n",
    "train_ligand_diversity = train_ligand_diversity.drop([\"pdb\", \"ligand_file\", \"chembl_id\", \"tanimoto_index\", \"smiles\"], axis=1)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 141,
   "id": "0cc53ec7-432d-4f83-94ad-dad2134b08cb",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "(6737, 5)\n",
      "(6737, 126)\n"
     ]
    }
   ],
   "source": [
    "print(train_ligand_diversity_meta.shape)\n",
    "print(train_ligand_diversity.shape)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 148,
   "id": "ba297498-e8d8-44bb-b1c6-4d4a4e722fe7",
   "metadata": {},
   "outputs": [],
   "source": [
    "train_ligand_diversity_meta.to_csv(\"work/training/dual-model/train-meta-ligand-diversity.csv\", sep=\",\", index=False, encoding=\"utf-8\")\n",
    "train_ligand_diversity.to_csv(\"work/training/dual-model/train-ligand-diversity.csv\", sep=\",\", index=False, encoding=\"utf-8\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "id": "d3052f4b-75cc-4329-a04a-44cc07da4c7b",
   "metadata": {},
   "outputs": [],
   "source": []
  },
  {
   "cell_type": "code",
   "execution_count": 143,
   "id": "4772c38c-4ab0-4de0-8cf4-5f9e01b33af8",
   "metadata": {},
   "outputs": [],
   "source": [
    "test_ligand_diversity_meta = test_ligand_diversity[[\"pdb\", \"ligand_file\", \"chembl_id\", \"tanimoto_index\", \"smiles\"]]\n",
    "test_ligand_diversity = test_ligand_diversity.drop([\"pdb\", \"ligand_file\", \"chembl_id\", \"tanimoto_index\", \"smiles\"], axis=1)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 144,
   "id": "4750e26c-89be-4145-a77f-df10c1577292",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "(1684, 5)\n",
      "(1684, 126)\n"
     ]
    }
   ],
   "source": [
    "print(test_ligand_diversity_meta.shape)\n",
    "print(test_ligand_diversity.shape)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 149,
   "id": "24bca0fb-8913-403a-b29f-bdf41d86de42",
   "metadata": {},
   "outputs": [],
   "source": [
    "test_ligand_diversity_meta.to_csv(\"work/training/dual-model/test-meta-ligand-diversity.csv\", sep=\",\", index=False, encoding=\"utf-8\")\n",
    "test_ligand_diversity.to_csv(\"work/training/dual-model/test-ligand-diversity.csv\", sep=\",\", index=False, encoding=\"utf-8\")"
   ]
  }
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