Imidazole Pyrazole Pyrrole 1,2,3-Triazole 1,2,4-Triazole Tetrazole

Furan Thiophene Isoxazole Oxazole Thiazole Isothiazole Oxadiazole 1,2,4-Oxadiazole 1,3,4-Oxadiazole 1,3,4-Thiadiazole Thiadiazole 1,2,5-Oxadiazole Dithiolane Trithiolane

Benzene Pyridine Pyrimidine Pyrazine Pyridazine Triazine Tetrazine Oxazine Thiazine

Morpholine Piperazine Piperidine Pyrrolidine Thiomorpholine Azetidine Aziridine Imidazolidine Oxazolidine Pyrazolidine Thiazolidine Pipecolinyl ring Azepane Dihydropyridine Hexahydropyrimidine Tetrahydropyrimidine Diazepane

Tetrahydrofuran Tetrahydropyran Oxirane Oxetane Dioxane Dioxolane Thiolane Tetrahydrothiopyran Oxepane Thietane Thiirane Trioxane

Indole Quinoline Benzimidazole Indazole Isoquinoline Quinazoline Quinoxaline Benzothiazole Benzoxazole Benzofuran Benzothiophene Benzotriazole Naphthalene Coumarin Acridine Benzisothiazole Benzisoxazole Carbazole Indoline Isoindole Naphthyridine Phthalazine Tetrahydroisoquinoline Tetrahydroquinoline Anthracene Cinnoline Flavone Phenanthrene Phenanthridine Phenothiazine Phenoxazine Isoindolinone Oxindole Benzodioxole Benzodioxane Benzomorpholine Chromane Chromanone Chromene Dihydrobenzofuran Xanthone Dibenzofuran Dibenzothiophene Fluorene Xanthene

Purine Adenine Guanine Xanthine Cytosine Hypoxanthine Uracil Imidazo[1,2-a]pyridine Pteridine Pyrazolo[1,5-a]pyridine Thymine Furanopyrimidine Pyrazolo[1,5-a]pyrimidine Thienopyrimidine

Steroid core Cyclohexane Cyclopropane Cyclopentane Decalin Adamantane Cyclobutane Spirocycle Cycloheptane

β-Lactam Acrylamide Quinone Michael acceptor Vinyl sulfone Boronic acid warhead Chloroacetamide α-Cyanoacrylamide Aldehyde warhead Epoxide warhead Fluoroacetamide Nitrile warhead Thiol-reactive Aza-Michael acceptor Isocyanate warhead Diacyl peroxide

α-Amino acid Catechol Biphenyl Salicylate Hydroquinone Resorcinol Chalcone Nucleoside sugar Pyranose sugar Stilbene Polyol

H-bond acceptor N H-bond acceptor O H-bond donor Ionizable base Lipinski HMW fragment P-gp efflux flag

ATP mimic purine ATP mimic pyrimidine Hinge binder (C=O-NH) Hinge binder (NH-C=O) Gatekeeper aromatic

Quinone alert Nitroaromatic Aldehyde (PAINS) Haloamide alert Michael acceptor (extended) Metal chelator PAINS — catechol PAINS — rhodanine

Peptide backbone Proline-like ring Sulfonamide bioisostere N-Methyl amide β-Turn mimetic Retro-amide