Fig. 1

Maximal common substructure (MCS) between diazepam (in red) and other marketed drugs and metabolites. The size of the MCS is plotted for various drugs (blue) and endogenous metabolites (green). A KNIME workflow was constructed, including using the RDKit MCS module and interrogated with the structure of diazepam. a Distribution of MCS values when the RDKit MCS was set to use only intact rings. b The same without that restriction. In both cases, the structures of the closest molecules are shown. c A comparison of the Tanimoto similarity of diazepam and other drugs and endogenites using two common fingerprint encodings (ECFP4 and MACCS). The structures of those exceeding 0.5 in each encoding are shown.