rdkit.Chem.MACCSkeys module — The RDKit 2016.09.1 documentation

# rdkit.Chem.MACCSkeys module

SMARTS definitions for the publically available MACCS keys and a MACCS fingerprinter

I compared the MACCS fingerprints generated here with those from two other packages (not MDL, unfortunately). Of course there are disagreements between the various fingerprints still, but I think these definitions work pretty well. Some notes:

1. most of the differences have to do with aromaticity

2) there’s a discrepancy sometimes because the current RDKit definitions do not require multiple matches to be distinct. e.g. the SMILES C(=O)CC(=O) can match the (hypothetical) key O=CC twice in my definition. It’s not clear to me what the correct behavior is. 3) Some keys are not fully defined in the MDL documentation 4) Two keys, 125 and 166, have to be done outside of SMARTS. 5) Key 1 (ISOTOPE) isn’t defined

Rev history: 2006 (gl): Original open-source release May 2011 (gl): Update some definitions based on feedback from Andrew Dalke