Merge branch 'dev' of github.com:CDDLeiden/QSPRpred into dev

qsprpred/data/chem/clustering.py

@@ -6,7 +6,7 @@
 from rdkit import Chem, DataStructs
 from rdkit.SimDivFilters import rdSimDivPickers
 
-from .scaffolds import Murcko, Scaffold
+from .scaffolds import BemisMurckoRDKit, Scaffold
 from .. import MoleculeTable
 from ..descriptors.fingerprints import Fingerprint, MorganFP
 from ...logs import logger
@@ -89,7 +89,7 @@ class ScaffoldClusters(MoleculeClusters):
         scaffold (Scaffold): scaffold generator
     """
 
-    def __init__(self, scaffold: Scaffold = Murcko()):
+    def __init__(self, scaffold: Scaffold = BemisMurckoRDKit()):
         super().__init__()
         self.scaffold = scaffold
 

qsprpred/data/chem/scaffolds.py

@@ -33,20 +33,14 @@ def supportsParallel(self) -> bool:
         return True
 
 
-class Murcko(Scaffold):
-    """Class for calculating Murcko scaffolds of a given molecule."""
+class BemisMurckoRDKit(Scaffold):
+    """Class for calculating Murcko scaffolds of a given molecule
+    using the default implementation in RDKit. If you want, an implementation
+    closer to the original paper, see the `BemisMurcko` class.
 
-    def __call__(self, mols, props, *args, **kwargs):
-        """
-        Calculate the Murcko scaffold for a molecule as implemented
-        in RDKit.
-
-        Args:
-            mol: SMILES as `str` or an instance of `Mol`
+    """
 
-        Returns:
-            SMILES of the Murcko scaffold as `str`
-        """
+    def __call__(self, mols, props, *args, **kwargs):
         res = []
         for mol in mols:
             mol = Chem.MolFromSmiles(mol) if isinstance(mol, str) else mol
@@ -55,7 +49,7 @@ def __call__(self, mols, props, *args, **kwargs):
         return pd.Series(res, index=props[self.idProp])
 
     def __str__(self):
-        return "Murcko"
+        return "BemisMurckoRDKit"
 
 
 class BemisMurcko(Scaffold):
@@ -114,15 +108,6 @@ def findTerminalAtoms(mol):
         return res
 
     def __call__(self, mols, props, *args, **kwargs):
-        """
-        Calculate the Bemis-Murcko scaffold for a molecule.
-
-        Args:
-            mol: SMILES as `str` or an instance of `Mol`
-
-        Returns:
-            SMILES of the Bemis-Murcko scaffold as `str`
-        """
         res = []
         for mol in mols:
             mol = Chem.MolFromSmiles(mol) if isinstance(mol, str) else mol

qsprpred/data/chem/tests.py

@@ -3,7 +3,7 @@
 
 from ... import TargetTasks
 from ...data import QSPRDataset
-from ...data.chem.scaffolds import Murcko, BemisMurcko
+from ...data.chem.scaffolds import BemisMurckoRDKit, BemisMurcko
 from ...utils.testing.base import QSPRTestCase
 from ...utils.testing.path_mixins import DataSetsPathMixIn
 
@@ -19,7 +19,7 @@ def setUp(self):
 
     @parameterized.expand(
         [
-            ("Murcko", Murcko()),
+            ("Murcko", BemisMurckoRDKit()),
             ("BemisMurcko", BemisMurcko()),
             ("BemisMurckoCSK", BemisMurcko(True, True)),
             ("BemisMurckoJustCSK", BemisMurcko(False, True)),

qsprpred/data/sampling/splits.py

@@ -18,7 +18,7 @@
     RandomClusters,
     ScaffoldClusters,
 )
-from ...data.chem.scaffolds import Murcko, Scaffold
+from ...data.chem.scaffolds import BemisMurckoRDKit, Scaffold
 from ...data.tables.base import MoleculeDataTable, DataSetDependant
 from ...data.tables.qspr import QSPRDataset
 from ...logs import logger
@@ -476,7 +476,7 @@ class ScaffoldSplit(GBMTDataSplit):
     def __init__(
         self,
         dataset: QSPRDataset | None = None,
-        scaffold: Scaffold = Murcko(),
+        scaffold: Scaffold = BemisMurckoRDKit(),
         test_fraction: float = 0.1,
         n_folds: int = 1,
         custom_test_list: list | None = None,
@@ -552,10 +552,10 @@ def setSeed(self, seed: int | None):
         self.seed = seed
         if hasattr(self.clustering, "seed"):
             self.clustering.seed = seed
-            
+
     def getSeed(self):
         """Get the seed for this instance.
-        
+
         Returns:
             int: the seed for this instance or None if no seed is set.
         """

qsprpred/data/sampling/tests.py

@@ -16,7 +16,7 @@
     FPSimilarityLeaderPickerClusters,
     FPSimilarityMaxMinClusters,
 )
-from ...data.chem.scaffolds import Murcko, BemisMurcko
+from ...data.chem.scaffolds import BemisMurckoRDKit, BemisMurcko
 from ...data.sampling.folds import FoldsFromDataSplit
 from ...data.sampling.splits import ManualSplit
 from ...utils.testing.base import QSPRTestCase
@@ -109,13 +109,13 @@ def testTemporalSplit(self, multitask):
 
     @parameterized.expand(
         [
-            (False, Murcko(), None),
+            (False, BemisMurckoRDKit(), None),
             (
                 False,
                 BemisMurcko(use_csk=True),
                 ["ScaffoldSplit_000", "ScaffoldSplit_001"],
             ),
-            (True, Murcko(), None),
+            (True, BemisMurckoRDKit(), None),
         ]
     )
     def testScaffoldSplit(self, multitask, scaffold, custom_test_list):

qsprpred/data_CLI.py

@@ -15,6 +15,10 @@
 from sklearn.impute import SimpleImputer
 from sklearn.preprocessing import StandardScaler
 
+from qsprpred.data.chem.clustering import (
+    FPSimilarityMaxMinClusters,
+    FPSimilarityLeaderPickerClusters,
+)
 from qsprpred.data.descriptors.fingerprints import (
     MorganFP,
     RDKitMACCSFP,
@@ -24,10 +28,6 @@
     RDKitFP,
     AvalonFP,
 )
-from qsprpred.data.chem.clustering import (
-    FPSimilarityMaxMinClusters,
-    FPSimilarityLeaderPickerClusters
-)
 from qsprpred.data.descriptors.sets import (
     DrugExPhyschem,
     PredictorDesc,
@@ -49,7 +49,7 @@
 )
 from qsprpred.data.tables.qspr import QSPRDataset
 from qsprpred.tasks import TargetTasks
-from .data.chem.scaffolds import Murcko
+from .data.chem.scaffolds import BemisMurckoRDKit
 from .extra.gpu.models.dnn import DNNModel
 from .logs.utils import backup_files, enable_file_logger
 from .models.scikit_learn import SklearnModel
@@ -363,7 +363,7 @@ def QSPR_dataprep(args):
                         else None,
                         "imputer": SimpleImputer(strategy=args.imputation[prop])
                         if prop in args.imputation
-                        else None
+                        else None,
                     }
                 )
             dataset_name = (
@@ -391,7 +391,7 @@ def QSPR_dataprep(args):
             if args.split == "scaffold":
                 split = ScaffoldSplit(
                     test_fraction=args.split_fraction,
-                    scaffold=Murcko(),
+                    scaffold=BemisMurckoRDKit(),
                     dataset=mydataset,
                 )
             elif args.split == "time":
@@ -525,12 +525,15 @@ def QSPR_dataprep(args):
         os.makedirs(args.output_dir)
 
     # get a list of all the folders in the output directory
-    folders = [f for f in os.listdir(args.output_dir) if os.path.isdir(f"{args.output_dir}/{f}")]
+    folders = [
+        f
+        for f in os.listdir(args.output_dir)
+        if os.path.isdir(f"{args.output_dir}/{f}")
+    ]
 
     # remove folders that start with backup
     folders = [f for f in folders if not f.startswith("backup")]
 
-
     if not args.skip_backup:
         backup_msg = backup_files(
             args.output_dir,

tutorials/basics/data/data_splitting.ipynb

@@ -1299,10 +1299,10 @@
     }
    ],
    "source": [
-    "from qsprpred.data.chem.scaffolds import Murcko\n",
+    "from qsprpred.data.chem.scaffolds import BemisMurckoRDKit\n",
     "from qsprpred.data import ScaffoldSplit\n",
     "\n",
-    "split = ScaffoldSplit(n_folds=10, scaffold=Murcko())\n",
+    "split = ScaffoldSplit(n_folds=10, scaffold=BemisMurckoRDKit())\n",
     "for fold, (X_train, X_test, y_train, y_test, train_index, test_index) in enumerate(\n",
     "        dataset.iterFolds(split)):\n",
     "    print_cv_split(fold, X_train, X_test, y_train, y_test, train_index, test_index)"
@@ -1805,7 +1805,7 @@
    "source": [
     "CrossValAssessor(\n",
     "    scoring=\"roc_auc\",\n",
-    "    split=ScaffoldSplit(n_folds=10, scaffold=Murcko())\n",
+    "    split=ScaffoldSplit(n_folds=10, scaffold=BemisMurckoRDKit())\n",
     ")(model, dataset)"
    ]
   },