A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
| Member | Definition | Role |
|---|
| (1-hydroxycyclopentyl)phenylacetic acid | (1-hydroxycyclopentyl)acetic acid in which one of the hydrogens alpha to the carboxylic acid group is substituted by a phenyl group. | (1-hydroxycyclopentyl)phenylacetic acid |
| 16beta,17-dihydroxy-ent-kaurane-19-oic acid | A ent-kaurane diterpenoid that is ent-kaurane-19-oic acid substituted by hydroxy groups at positions 16 and 17 (the 16beta stereoisomer). It is isolated from Helianthus sp. and Annona squamosa and exhibits anti-HIV activity. | 16beta,17-dihydroxy-ent-kaurane-19-oic acid |
| 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol | An aromatic ether that is diphenyl ether substituted by a 2-hydroxy-1-(1H-1,2,4-triazol-1-yl)propan-2-yl group at position 1, trifluoromethyl group at position 2 and a chloro group at position 4. | 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol |
| 2-phenyl-2-propanol | A tertiary alcohol that is isopropanol in which the hydrogen attached to the carbon bearing the hydroxy group has been replaced by a phenyl group. | 2-phenylpropan-2-ol |
| 3-hydroxy-3-methylbutene | A tertiary alcohol that is 3-methylbut-1-ene carrying a hydroxy substituent at position 3. | 3-hydroxy-3-methylbut-1-ene |
| 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol | A terpineol that is 1-menthene carrying a hydroxy substituent at position 4. | 4-terpineol |
| aclacinomycin | An anthracycline that is aklavinone having an alpha-L-rhodosaminyl residue attached at position 4 via a glycosidic linkage. | aclacinomycin T zwitterion; aclacinomycin T |
| aeroplysinin i | | Aeroplysinin 1 |
| aflatoxin m1 | A member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at position 9a is replaced by a hydroxy group. | aflatoxin M1 |
| aklavinone | | aklavinone |
| alpha-cadinol | A cadinane sesquiterpenoid that is cadin-4-ene carrying a hydroxy substituent at position 10. | alpha-cadinol |
| alpha-eudesmol | A eudesmane sesquiterpenoid in which the eudesmane skeleton carries a hydroxy substituent at C-11 and has a double bond between C-3 and C-4. | alpha-eudesmol |
| ambrein | A triterpenoid alcohol that is a constituent of ambergris, an intestinal secretion of the sperm whale Physeter catodon. | ambrein |
| ancymidol | A tertiary alcohol that is methanol in which the hydrogens attached to the carbon are replaced by cyclopropyl, p-methoxyphenyl and pyrimidin-5-yl groups. By inhibiting gibberellin biosynthesis, ancymidol reduces plant growth, resulting in reduced internode elongation and thus more compact plants. It is used in the commercial production of a wide variety of container-grown bedding and foliage plants, including chrysanthemums, Easter lilies and poinsettias. | ancymidol |
| arisugacin | An organic heterotetracyclic compound that is 4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-b]chromene-1,11(5H)-dione substituted by 3,4-dimethoxyphenyl group at position 9 (the 4aR,6aR,12aS,12bS steroisomer). Isolated from the culture broth of Penicillium, it acts as a selective inhibitor of acetylcholinesterase. | arisugacin A |
| asperfuranone | A member of the class of 2-benzofurans that is 6,7-dihydro-2-benzofuran-4(5H)-one that is substituted at positions 5 and 6 by hydroxy groups, at position 5 by a methyl group and at position 1 by a (2E,4E,6S)-4,6-dimethylocta-2,4-dienoyl group (the 5S,6R-diastereoisomer). A polyketide that was first obtained from the fungus Aspergillus nidulans by using a genomic mining approach. | asperfuranone |
| asukamycin | A polyketide that is a member of the manumycin family of antibiotics and exhibits strong antibacterial, antifungal, and antineoplastic activities. Isolated from from the actinomycete bacterium Streptomyces nodosus subsp. asukaensis. | asukamycin |
| aurachin a | An A-type aurichin that is 1,2-dihydrofuro[2,3-c]quinoline 5-oxide which is substituted at position 2 by a (6E)-10-hydroxy-2,6-dimethylundeca-2,6-dien-10-yl group and at position 4 by a methyl group (relative configuration shown). Found in the myxobacterium Stigmatella aurantiaca strain Sg a15. | aurachin A |
| azadirachtin | A member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica). | azadirachtin A |
| azd 7545 | A sulfone that is benzene substituted by [4-(dimethylcarbamoyl)phenyl]sulfonyl, chloro and [(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino groups at positions 1, 3 and 4, respectively. It is a potent and non-ATP-competitive inhibitor of pyruvate dehydrogenase kinase 2 (PDHK2) with IC50 of 6.4 nM and exhibits glucose-lowering activity. Also inhibits PDHK1 at higher levels (IC50 = 36.8 nM). | AZD7545 |
| bacterioruberin | A C50 carotenoid that is a red-coloured pigment found in several Halobacterium and Haloarcula species. | bacterioruberin |
| bedaquiline | A quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria. | bedaquiline |
| benzoylaconine | A diterpene alkaloid with formula C32H45NO10 that is isolated from several Aconitum species. | benzoylaconine |
| benzoylmesaconine | A diterpene alkaloid with formula C31H43NO10 that is isolated from several Aconitum species. | benzoylmesaconine |
| berkeleydione | A meroterpenoid found in Penicillium rubrum. It has been shown to exhibit inhibitory activity against caspase-1. | berkeleydione |
| berkeleytrione | A meroterpenoid found in Penicillium rubrum and has been shown to exhibit inhibitory activity against caspase-1. | berkeleytrione |
| beta-eudesmol | A carbobicyclic compound that is trans-decalin substituted at positions 2, 4a, and 8 by 2-hydroxypropan-2-yl, methyl and methylidene groups, respectively (the 2R,4aR,8aS-diastereoisomer). | beta-eudesmol |
| bicalutamide | A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group. | N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide |
| biperiden | A member of the class of piperidines that is N-propylpiperidine in which the methyl hydrogens have been replaced by hydroxy, phenyl, and 5-norbornen-2-yl groups. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all forms of Parkinson's disease. | biperiden |
| biperiden hydrochloride | The hydrochloride salt of biperiden. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all forms of Parkinson's disease. | biperiden hydrochloride |
| blister | A pyrroloquinoline that is 1,2,3,3a-tetrahydro-H-pyrrolo[2,3-b]quinolin-4-one substituted by a hydroxy group at position 3a, a methyl group at position 6 and a phenyl group at position 1. It acts as an inhibitor of ATPase activity of non-muscle myosin II. | blebbistatin |
| bms 477118 | A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-amino(3-hydroxyadamantan-1-yl)acetic acid with the amino group of (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile. Used in its monohydrate form for the treatment of Type II diabetes. | saxagliptin |
| brazilin | A organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood). | brazilin |
| bromophycolide a | A diterpenoid that is a macrolide isolated from the Fijian red alga Callophycus serratus. It has been found to exhibit moderate cytotoxicity against several human tumour cell lines via specific apotopic cell death. It also displays anti-HIV, antibacterial, antifungal and antimalarial activity. | bromophycolide A |
| butaclamol | An organic heteropentacyclic compound that is 2,3,4,4a,8,9,13b,14-octahydro-1H-benzo[6,7]cyclohepta[1,2,3-de]pyrido[2,1-a]isoquinoline substituted at position 3 by both hydroxy and tert-butyl groups. | (+)-butaclamol |
| cafestol | An organic heteropentacyclic compound and furan diterpenoid with formula C20H28O3 obtained from the unsaponifiable fraction of coffee oil (a lipid fraction obtained from coffee beans by organic solvent extraction). | cafestol |
| camptothecin | A pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-b]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at position 4 (the S enantiomer). | camptothecin |
| caribenol a | A terpene lactone that is 3,4,5,5a,6,7,7a,10,10a,10b-decahydro-2H-1-oxabenzo[cd]cyclopenta[h]azulen-2-one substituted by a hydroxy group at position 10b and methyl groups at positions 3, 6, 9 and 10a. It is isolated from the West Indian gorgonian octocoral Pseudopterogorgia elisabethae and exhibits antitubercular and antimalarial activity. | caribenol A |
| cedrol | | cedrol |
| chlorobutanol | | chlorobutanol |
| cinnamodial | | Cinnamodial |
| columbianetin | The angular furanocoumarin analogue of the linear furanocoumarin marmesin. | columbianetin |
| cubebol | A tertiary alcohol resulting from the formal addition of water to the double bond of alpha-cubebene. | (-)-cubebol |
| cyclooctatin | A diterpenoid characterized by a 5-8-5 dodecahydrodicyclopenta[a,d]cyclooctene fused-ring system, with a single double bond and one isopropyl, two hydroxy, one hydroxymethyl and two methyl substituents. | cyclooctatin |
| cyclopentolate | A carboxylic ester resulting from the formal condensation of (1-hydroxycyclopentyl)(phenyl)acetic acid with N,N-dimethylethanolamine. A tertiary amine antimuscarinic with actions similar to atropine, it is used as its hydrochloride salt to produce mydriasis (excessive dilation of the pupil) and cycloplegia (paralysis of the ciliary muscle of the eye) for opthalmic diagnostic procedures. It acts more quickly than atropine and has a shorter duration of action. | cyclopentolate |
| cycrimine | A member of the class of piperidines that is 3-(piperidin-1-yl)propan-1-ol in which one of the hydrogen atoms at the 1-position is substituted by cyclopentyl, and the other is substituted by phenyl. A central anticholinergic, it is used as its hydrochloride salt in the management and treatment of Parkinson's disease. | cycrimine |
| cyproconazole | A tertiary alcohol that is butan-2-ol substituted by a 4-chlorophenyl group at position 2, a cyclopropyl group at position 3 and a 1H-1,2,4-triazol-1-yl group at position 1. | 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol |
| deltaline | | deltaline |
| dicofol | A tertiary alcohol that is DDT in which the benzylic hydrogen has been replaced by a hydroxy group. | dicofol |
| diflomotecan | An organic heteropentacyclic compound that is (5R)-8-[(6,7-difluoroquinolin-3-yl)methyl]-5-ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine moiety is joined to position 3 of the difluoroquinoine ring by a single bond. An E-ring modified camptothecin analogue that has greater lactone stability in plasma compared with other topoisomerase I inhibitors. | diflomotecan |
| diphenidol | A tertiary alcohol that is butan-1-ol substituted by two phenyl groups at position 1 and a piperidin-1-yl group at position 4. | diphenidol |
| diplopterol | A hopanoid that is hopane substituted by a hydroxy group at position 22. | hopan-22-ol |
| diversonol | | (+)-diversonol |
| efinaconazole | A member of the class of triazoles that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,4-difluorophenyl, and 4-methylenepiperidin-1-yl groups, respectively (the 2R,3R stereoisomer). It is an antifungal drug used for the topical treatment of onychomycosis (a nail infection caused mainly by dermatophytes). | efinaconazole |
| elemol | A sesquiterpenoid that is isopropanol which is substituted at position 2 by a (3S,4S)-3-isopropenyl-4-methyl-4-vinylcyclohexyl group. | elemol |
| enasidenib | A 1,3,5-triazine which is substituted by (2-hydroxy-2-methylpropyl)nitrilo, 6-(trifluoromethyl)pyridin-2-yl and [2-(trifluoromethyl)pyridin-4-yl]nitrilo groups at positions 2,4 and 6, respectively. It is an isocitrate dehydrogenase-2 (IDH2) inhibitor which has been approved for the treatment of adults with relapsed or refractory acute myeloid leukaemia (AML). | enasidenib |
| ethisterone | A 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol. | ethisterone |
| ethylestrenol | A 17beta-hydroxy steroid that is estrane containing a double bond between positions 4 and 5 and substituted by an ethyl group and a hydroxy group at the 17alpha and 17beta positions, respectively. It is an anabolic steroid that has little androgenic effect and only slight progestational activity. It has been used to promote growth in boys with delayed bone growth. | ethylestrenol |
| eurycomanone | A quassinoid isolated from Eurycoma longifolia and has been shown to exhibit antineoplastic and antimalarial activties. | eurycomanone |
| fenarimol | A member of the class of pyrimidines that is pyrimidin-5-ylmethanol in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 2-chlorophenyl group while the other is replaced by a 4-chlorophenyl group. | (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol |
| fluconazole | A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis. | fluconazole |
| flutriafol | A tertiary alcohol that is ethanol in which one of the hydrogens at position 1 is replaced by an p-fluorophenyl group, the other hydrogen at position 1 is replaced by a p-fluorophenyl group, and one of the hydrogens at position 2 is replaced by a 1H-1,2,4-triazol-1-yl group. | 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol |
| gardenoside | A cyclopentapyran that is 7-deoxyloganin with a methyl and hydrogen replaced by hydroxy and hydroxymethyl groups at position 7. | gardenoside |
| gdc-0973 | A member of the class of N-acylazetidines obtained by selective formal condensation of the carboxy group of 3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoic acid with the secondary amino group from the azetidine ring of 3-[(2S)-piperidin-2-yl]azetidin-3-ol. An inhibitor of mitogen-activated protein kinase that is used (as its fumarate salt) in combination with vemurafenib for the treatment of patients with unresectable or metastatic melanoma. | cobimetinib |
| germacradienol | A germacrane sesquiterpenoid obtained from germacrane by hydroxylation at C(11) together with dehydrogenation across the C(1)-C(10) and C(5)-C(6) bonds. | (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol |
| grayanotoxin i | A tetracyclic diterpenoid that is grayanotoxane in which the pro-R hydrogen at position 14 is substituted by an acetoxy group and in which the 3beta-, 5-, 6beta-, 10-, and 16- positions are substituted by hydroxy groups. | grayanotoxin I |
| grayanotoxin ii | | Grayanotoxin II |
| gsk690693 | A member of the class of imidazopyridines that is 4-(1-ethylimidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol carrying additional 2-(4-amino-1,2,5-oxadiazol-3-yl and [(3S)-piperidin-3-yl]methoxy substituents at positions 4 and 7 respectively. | GSK690693 |
| haloperidol | A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety. | haloperidol |
| hematoxylin | An organic heterotetracyclic compound 7,11b-dihydroindeno[2,1-c]chromene carrying five hydroxy substituents at positions 3, 4, 6a, 9 and 10. The most important and most used dye in histology, histochemistry, histopathology and in cytology. | haematoxylin |
| heptaminol | | 6-amino-2-methyl-2-heptanol |
| hexaconazole | A member of the class of triazoles that is 1-hexyl-1H-1,2,4-triazole in which the hydrogens at position 2 of the hexyl chain are replaced by hydroxy and 2,4-dichlorophenyl groups. | 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol |
| homocamptothecin | An organic heteropentacyclic compound that is (5R)-5-ethyl-5-hydroxy-8-(quinolin-3-ylmethyl)-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine group has been joined to position 2 of the quinoline ring by a single bond. A semisynthetic analogue of camptothecin, it is an inhibitor of topoisomerase I. | (R)-homocamptothecin |
| homoharringtonine | A cephalotaxine-derived alkaloid ester obtained from Cephalotaxus harringtonia; used for the treatment of chronic or accelerated phase chronic myeloid leukaemia. | omacetaxine mepesuccinate |
| hydroxycitronellal | The tertiary alcohol arising from addition of water across the C=C double bond of citronellal. | hydroxycitronellal |
| hydroxyibuprofen | A hydroxy monocarboxylic acid that is ibuprofen in which the methine proton on the isobutyl group has been replaced by a hydroxy group. | 2-hydroxyibuprofen |
| inuviscolide | A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity. | inuviscolide |
| irinotecan | A member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active. | irinotecan |
| isavuconazole | A 1,3-thiazole that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,5-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively. It is an antifungal drug used for the treatment of invasive aspergillosis and invasive mucormycosis. | isavuconazole |
| josamycin | A macrolide antibiotic produced by certain strains of Streptomyces narbonensis var. josamyceticus. | josamycin |
| kahweol | A diterpenoid with formula C20H26O3, isolated from the beans of Coffea arabica. It exhibits antioxidant, anti-inflammatory, anti-angiogenesis and anti-proliferative properties. | kahweol |
| kt 5720 | An organic heterooctacyclic compound that is 1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of hexyl (3S)-3-hydroxy-2-methyltetrahydrofuran-3-carboxylate (the 2R,3S,5S product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1,5-dihydro-2H-pyrrol-2-one. | KT 5720 |
| kt 5926 | An organic heterooctacyclic compound that is 5-propoxy-1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of methyl (3R)-3-hydroxy-2-methyltetrahydrofuran-3-carboxylate (the 2S,3R,5R product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1,5-dihydro-2H-pyrrol-2-one. | KT 5926 |
| lasalocid | A polyether antibiotic used for prevention and treatment of coccidiosis in poultry. | lasalocid |
| linalool | A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum. | linalool |
| loperamide | A synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease. | loperamide |
| manool | A labdane diterpenoid in which the labdane skeleton has double bonds at positions 8(17) and 14 and carries an R-hydroxy group at position 13. | manool |
| manumycin | A polyketide with formula C31H38N2O7 initially isolated from Streptomyces parvulus as a result of a random screening program for farnesyl transferase (FTase) inhibitors. It is a natural product that exhibits anticancer and antibiotic properties. | manumycin A |
| megestrol acetate | A sesquiterpene lactone with formula C15H20O8. It is a neurotoxic natural product found in plants of the family Illiciaceae. | anisatin |
| meglutol | A dicarboxylic acid that is glutaric acid in which one of the two hydrogens at position 3 is substituted by a hydroxy group, while the other is substituted by a methyl group. It has been found to accumulate in urine of patients suffering from HMG-CoA lyase (3-hydroxy-3-methylglutaryl-CoA lyase, EC 4.1.3.4) deficiency. It occurs as a plant metabolite in Crotalaria dura. | 3-hydroxy-3-methylglutaric acid |
| metconazole | A member of the class of cyclopentanols carrying 1,2,4-triazol-1-ylmethyl and 4-chlorobenzyl and geminal dimethyl substituents at positions 1, 2 and 5 respectively. Used to control a range of fungal infections including alternaria, rusts, fusarium and septoria diseases. | metconazole |
| methampicillin | A member of the class of triazoles that is butan-2-ol which is substituted at positions 2, 3, and 4 by phenyl, 1H-1,2,4-triazol-1-yl and p-chlorophenyl groups, respectively. An inhibitor of brassinosteroid biosynthesis. | brassinazole |
| myrocin a | | Myrocin A |
| n-demethylloperamide | A monocarboxylic acid amide that is the methylamide of 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanoic acid. | desmethyl loperamide |
| naloxegol | An organic heteropentacyclic compound that is naloxone in which the keto group is replaced by a PEG moiety. Used for treatment of opioid-induced constipation. | naloxegol |
| naloxone | A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose. | naloxone |
| norethindrone | A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen. | norethisterone |
| ophiobolin a | A sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo groups at positions 5 and 25, double bonds at positions 7-8 and 19-20, and an oxygen link between positions 14 and 18. | ophiobolin A |
| oplodiol | A carbobicyclic compound that is 1,2,3,4,4a,5,8,8a-octahydronaphthalene which is substituted by hydroxy groups at positions 1 and 4, an isoopropyl group at position 7, and by methyl groups at positions 1 and 4a (the 1S,4R,4aR,8aR isomer). A sesquiterpenoid plant metabolite. | oplodiol |
| ossamycin | A macrolide antibiotic that was originally isolated from the culture broths of Streptomyces hygroscopicus var. ossamyceticus. | ossamycin |
| Ovalicine subst. | | Ovalicine subst. |
| oxybutynin | A carboxylic ester resulting from the formal condensation of the carboxy group of cyclohexyl(hydroxy)phenylacetic acid with the hydroxy group of 4-(diethylamino)but-2-yn-1-ol. | 4-(diethylamino)but-2-yn-1-ol; oxybutynin |
| papuamide b | A cyclodepsipeptide that is isolated from Papua New Guinea collections of the marine sponges Theonella mirabilis and Theonella swinhoei. It exhbits anti-HIV-1 activity and cytotoxicity against some human cancer cell lines. | papuamide B |
| paxilline | An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels. | paxilline |
| phorbol | A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions. | phorbol |
| picrotin | An organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. | picrotin |
| picrotoxinin | A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin. | picrotoxinin |
| praliciguat | A member of the class of pyrazoles that is 5-fluoro-2-(1H-pyrazol-3-yl)pyrimidine which is substituted by a 2-fluorobenzyl group at position 1, 1,2-oxazol-3-yl group at position 5, and by a [3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]nitrilo group at position 4. It is a soluble guanylate cyclase stimulator under clinical development for the treatment of heart failure with preserved ejection fraction. | praliciguat |
| pridinol | A piperidine substituted at position 1 by a 3-hydroxy-3,3-diphenylpropyl group. | pridinol |
| procyclidine | A tertiary alcohol that consists of propan-1-ol substituted by a cyclohexyl and a phenyl group at position 1 and a pyrrolidin-1-yl group at position 3. | procyclidine |
| prothioconazole | A member of the class of triazoles that is 1,2,4-triazole-3-thione substituted at position 2 by a 2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl group. | 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione |
| ravuconazole | A member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14alpha demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4) | ravuconazole |
| rhodopin | A carotenol having the structure of 1,2-dihydro-psi,psi-carotene with a hydroxy function at C-1. | rhodopin |
| riddelliine n-oxide | A pyrrolizine alkaloid that is 13,19-didehydrosenecionane bearing two additional hydroxy substituents at positions 12 and 18, two additional oxo groups at positions 11 and 16 and an N-oxido substituent. | riddelliine N-oxide |
| rubitecan | A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin. | rubitecan |
| senecionine | A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio. | senecionine |
| sn 38 | A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself. | SN-38 |
| spathulenol | A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. | spathulenol |
| sporidesmin | An organic heteropentacyclic compound that has formula C18H20ClN3O6S2, produced by the saprophyte fungus Pithomyces chartarum. It is a mycotoxin responsible for the hepatogenous photosensitisation disease facial eczema in ruminants. | sporidesmin A |
| squalestatin 1 | A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. | zaragozic acid A |
| stanozolol | An organic heteropentacyclic compound resulting from the formal condensation of the 3-keto-aldehyde moiety of oxymetholone with hydrazine. Like oxymetholone, it is a synthetic anabolic steroid. It has both anabolic and androgenic properties, and has been used to treat hereditary angioedema and various vascular disorders. It has also been widely abused by professional athletes. | stanozolol |
| staphyloferrin a | A D-ornithine derivative obtained by formal condensation of the terminal carboxy groups of two citric acid units with the two amino groups of D-ornithine. | staphyloferrin A |
| staphyloferrin b | A siderophore composed from L-2,3-diaminopropionic acid, citric acid, 1,2-diaminoethane and alpha-ketoglutaric acid units. | staphyloferrin B |
| t-cadinol | A cadinane sesquiterpenoid that is cadin-4-ene carrying a hydroxy substituent at position 10. | tau-cadinol |
| t-muurolol | A cadinane sesquiterpenoid that consists of 4-isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene having a hydroxy substituent at position 1 and (1S,4S,4aR,8aS)-configuration. | (-)-Tau-muurolol |
| tebuconazole | A tertiary alcohol that is pentan-3-ol substituted by a 4-chlorophenyl, methyl, methyl, and a 1H-1,2,4-triazol-1-ylmethyl at positions 1, 4, 4 and 3 respectively. | 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol |
| tert-amyl alcohol | A tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups. | 2-methylbutan-2-ol |
| tert-butyl alcohol | A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2. | tert-butanol |
| theogallin | A gallate ester resulting from the formal condensation of gallic acid with the (5R)-hydroxy group of (-)-quinic acid (i.e. the hydroxy group on the same side of the cyclohexane ring as the carboxy group). | theogallin |
| threo-alpha-methylisocitrate | A tricarboxylic acid that is butan-2-ol in which a hydrogen from each of positions 2, 3, and 4 has been replaced by carboxy groups. | 3-hydroxybutane-1,2,3-tricarboxylic acid |
| tmc-95a | A 17-membered macrocyclic lactam that incorporates a phenol and a substituted indole moiety. It includes a R-hydroxy group at position 11 and a (3-methyl-2-oxopentanoyl)amino group at position at position 18 with a S-methyl group. It acts as a proteasome inhibitor and is obtained from Apiospora montagnei Sacc. TC 1093, isolated from a soil sample. | TMC-95A |
| tmc-95b | A 17-membered macrocyclic lactam that incorporates a phenol and a substituted indole moiety. A stereoisomer of TMC-95A, it has a [(3R)-3-methyl-2-oxopentanoyl]amino group at position 18. It acts as a proteasome inhibitor and is isolated from Apiospora montagnei Sacc. TC 1093, isolated from a soil sample. | TMC-95B |
| tridihexethyl | | tridihexethyl |
| ultram | A tertiary alcohol that is cyclohexanol substituted at positions 1 and 2 by 3-methoxyphenyl and dimethylaminomethyl groups respectively. | 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol |
| venlafaxine | A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-methoxyphenyl group. | venlafaxine |
| vibrioferrin | A tricarboxylic acid that is citric acid in which the pro-R carboxy group has been esterified with the primary hydroxy group of 2-hydroxy-1-{(2S)-1-[(2-hydroxyethyl)amino]-1-oxopropan-2-yl}-5-oxoproline. It is a siderophore isolated from bacteria closely associated or symbiotic with toxic, bloom-forming dinoflagellates. | vibrioferrin |
| vibsanin b | A vibsane diterpenoid that is (2Z,6E,10E)-cycloundeca-2,6,10-trien-1-one which is substituted at positions 2, 5, 5, 8, 9, and 9 by hydroxymethyl, methyl, 2-methylpent-2-en-5-yl, 3-methylbut-2-enoyloxy, hydroxy, and methyl groups, respectively (the 5S,8R,9R stereoisomer). It has been found to inhibit root growth in rice seedlings (IC50 0.14 mM). | vibsanin B |
| vincaleukoblastine | | vincaleukoblastine |
| vincristine | A vinca alkaloid with formula C46H56N4O10 found in the Madagascar periwinkle, Catharanthus roseus. It is used (commonly as the corresponding sulfate salt)as a chemotherapy drug for the treatment of leukaemia, lymphoma, myeloma, breast cancer and head and neck cancer. | vincristine |
| vindesine | | vindesine |
| viridiflorol | A carbotricyclic compound that is (1aS,4aR,7aR,7bR)-decahydro-1H-cyclopropa[e]azulene carrying four methyl substituents at positions 1, 1, 4 and 7 as well as a hydroxy substituent at position 4. It is a sesquiterpenoid isolated from several plant species and is a strong feeding deterrent for the melaleuca weevil that retards larval development. | viridiflorol |
| voriconazole | A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4. | voriconazole |
| warburganal | | Warburganal |
| withanolide d | A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 22 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Tubocapsicum anomalum and Withania somnifera, it exhibits cytotoxic activity. | withanolide D |
| yunaconitine | A diterpene alkaloid with formula C35H49NO11 that is isolated from several Aconitum species. | yunaconitine |
| yw 3548 | A terpene lactone that is obtained from Codinea simplex and acts as an inhibitor of glycerophosphoinositol biosynthesis. | YW3548 |
| zaragozic acid c | A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. | zaragozic acid C |