BCUT-descriptor gives different values depending on SMILES coding of same molecule #735
Description
Dear CDK-Developers,
I am having an issue regarding the BCUT-Descriptor.
Working with the BCUT-Descriptor showed that the BCUT-descriptor values depend on the SMILES coding. The same molecule (isomorphic structure) coded in different SMILES gives different BCUT-values:
Example: Acetamide
// use outgoing (old) smiles
IAtomContainer tmpOutgoingAcetamide = sp.parseSmiles("C(C)(N)=O");
AtomContainerManipulator.convertImplicitToExplicitHydrogens(tmpOutgoingAcetamide );
// use absolute smiles generated using CDKs SmilesGenerator
IAtomContainer tmpAbsoluteAcetamide = sp.parseSmiles("CC(=O)N");
AtomContainerManipulator.convertImplicitToExplicitHydrogens(tmpAbsoluteAcetamide);
// calculate BCUT
BCUTDescriptor tmpBCutDesc = new BCUTDescriptor();
String resultBcutOutgoingAcetamide = tmpBCutDesc.calculate(tmpOutgoingAcetamide ).getValue().toString();
String resultBcutAbsoluteAcetamide = tmpBCutDesc.calculate(tmpAbsoluteAcetamide).getValue().toString();
gives:
for resultBcutOutgoingAcetamide :
11.98891018734743, 16.005924145494618, -0.36108523358916594, 0.2733616424867599, 3.3749867502901925, 4.991266689763892
for resultBcutAbsoluteAcetamide :
11.993832778266086, 15.994915651911281, -0.29718469746032156, 0.21853991312718152, 3.40274753607958, 4.981220894more examples as .pdf and .csv can be found here:
Dependency_BCUT_SMILES.zip
Since the BCUT-descriptor is the only descriptor whose values depend on the SMILES coding, I wanted to ask whether it is necessary to generate absolute SMILES in advance or could it be an internal issue?
Best regards,
Lisa