Figure 5

LBVS in ZINC (23.2 M 3D-structures) for analogs of 66 marketed drugs with two asymmetric centers. A. Cumulative area plot giving the number of unique compounds among 5000 3DXfp nearest neighbors of RR and RS diastereomers of each drug and 5000 Xfp nearest neighbors of the same drug as found only from RR (cyan), RS (yellow), Xfp (grey), RR and RS (green), RR and Xfp (blue), RS and Xfp (red), or in all three searches (black). The drugs (DrugBank code on x-axis) are sorted by decreasing number of RR-unique analogs. Examples of diastereomers of drugs are shown in overlayed magenta/cyan models of the energy minimized conformers used for LBVS. B. Same as A for the case of 3DAPfp and APfp as fingerprints.