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Add mol_registration_hash function #28

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758e3c3
feat: Add mol_registration_hash function
google-labs-jules[bot] Jan 11, 2026
b2865df
feat: Add mol_registration_hash function
google-labs-jules[bot] Jan 11, 2026
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3 changes: 3 additions & 0 deletions src/include/mol_descriptors.hpp
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Original file line number Diff line number Diff line change
@@ -1,5 +1,8 @@
#pragma once
#include "common.hpp"
#include "duckdb/main/connection.hpp"

namespace duckdb_rdkit {
void RegisterDescriptorFunctions(DatabaseInstance &instance);
void mol_registration_hash(DataChunk &args, ExpressionState &state, Vector &result);
}
27 changes: 27 additions & 0 deletions src/mol_descriptors.cpp
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Expand Up @@ -13,6 +13,8 @@
#include "qed.hpp"
#include "types.hpp"
#include "umbra_mol.hpp"
#include <GraphMol/MolHash/nmmolhash.h>
#include <sstream>

namespace duckdb_rdkit {

Expand Down Expand Up @@ -131,6 +133,26 @@
});
}

void mol_registration_hash(DataChunk &args, ExpressionState &state, Vector &result) {
D_ASSERT(args.data.size() == 1);
auto &binary_umbra_mol = args.data[0];
auto count = args.size();

UnaryExecutor::Execute<string_t, string_t>(
binary_umbra_mol, result, count, [&](string_t b_umbra_mol) {
auto umbra_mol = umbra_mol_t(b_umbra_mol);
auto bmol = umbra_mol.GetBinaryMol();
auto mol = rdkit_binary_mol_to_mol(bmol);

std::stringstream hash_stream;
hash_stream << "tautomer_smiles:" << RDKit::MolHash::MolHash(mol, RDKit::MolHash::HashFunction::HetAtomTautomer) << "\n";

Check failure on line 148 in src/mol_descriptors.cpp

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cannot convert 'std::unique_ptr<RDKit::ROMol>' to 'RDKit::RWMol*'

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cannot convert 'std::unique_ptr<RDKit::ROMol>' to 'RDKit::RWMol*'
hash_stream << "canonical_smiles:" << RDKit::MolHash::MolHash(mol, RDKit::MolHash::HashFunction::CanonicalSmiles) << "\n";

Check failure on line 149 in src/mol_descriptors.cpp

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cannot convert 'std::unique_ptr<RDKit::ROMol>' to 'RDKit::RWMol*'

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cannot convert 'std::unique_ptr<RDKit::ROMol>' to 'RDKit::RWMol*'
hash_stream << "mol_formula:" << RDKit::MolHash::MolHash(mol, RDKit::MolHash::HashFunction::MolFormula);

Check failure on line 150 in src/mol_descriptors.cpp

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cannot convert 'std::unique_ptr<RDKit::ROMol>' to 'RDKit::RWMol*'

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cannot convert 'std::unique_ptr<RDKit::ROMol>' to 'RDKit::RWMol*'

return StringVector::AddString(result, hash_stream.str());
});
}

void RegisterDescriptorFunctions(DatabaseInstance &instance) {
ScalarFunctionSet set_mol_amw("mol_amw");
set_mol_amw.AddFunction(
Expand Down Expand Up @@ -171,5 +193,10 @@
set_mol_num_rotatable_bonds.AddFunction(
ScalarFunction({duckdb_rdkit::Mol()}, LogicalType::INTEGER, mol_num_rotatable_bonds));
ExtensionUtil::RegisterFunction(instance, set_mol_num_rotatable_bonds);

ScalarFunctionSet set_mol_registration_hash("mol_registration_hash");
set_mol_registration_hash.AddFunction(
ScalarFunction({duckdb_rdkit::Mol()}, LogicalType::VARCHAR, mol_registration_hash));
ExtensionUtil::RegisterFunction(instance, set_mol_registration_hash);
}
} // namespace duckdb_rdkit
27 changes: 27 additions & 0 deletions test/sql/mol_registration_hash.test
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Original file line number Diff line number Diff line change
@@ -0,0 +1,27 @@
# Require statement will ensure this test is run with this extension loaded
require duckdb_rdkit

statement ok
CREATE TABLE molecules (m Mol, registration_hash VARCHAR);

statement ok
INSERT INTO molecules VALUES
(mol_from_smiles('CCO'), null),
(mol_from_smiles('C1=CC=CC=C1'), null);

statement ok
UPDATE molecules SET registration_hash=mol_registration_hash(m);

query I
SELECT registration_hash FROM molecules WHERE m = mol_from_smiles('CCO');
----
tautomer_smiles:CCO
canonical_smiles:CCO
mol_formula:C2H6O

query I
SELECT registration_hash FROM molecules WHERE m = mol_from_smiles('C1=CC=CC=C1');
----
tautomer_smiles:c1ccccc1
canonical_smiles:c1ccccc1
mol_formula:C6H6
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