Figure 7.

CheSS queries with alternative canonicalization identify functionally similar molecules with divergent structure

Results from the OEChem-canonicalized queries are shown, although RDKit Atom n also had structurally distinct functional analogues in the top 250 results.

(A) Nirmatrelvir, a peptidomimetic SARS-CoV-2 main protease inhibitor, returned a wide range of non-peptidomimetic protease and peptidase inhibitors.

(B) LSD, an ergoline 5-HT2A agonist, returned many non-ergoline 5-HT receptor ligands.

(C) Fentanyl, an elongated piperidine opioid agonist, returned several morphinan and non-fentanyl opiates.