| Member | Definition | Role |
|---|
| [(1S,2R,3S,4S,6R,7R,8R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate | | [(1S,2R,3S,4S,6R,7R,8R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate |
| 1-[1-(1,3-dioxo-2-indenylidene)ethyl]-4-piperidinecarboxylic acid ethyl ester | | 1-[1-(1,3-dioxo-2-indenylidene)ethyl]-4-piperidinecarboxylic acid ethyl ester |
| 1,5-anhydrofructose | | 1,5-anhydro-D-fructose |
| 2-(2-cyclohexylidenehydrazinyl)-1-cyclohepta-2,4,6-trienone | | 2-(2-cyclohexylidenehydrazinyl)-1-cyclohepta-2,4,6-trienone |
| 2-(thiophen-2-ylmethylidene)indene-1,3-dione | | 2-(thiophen-2-ylmethylidene)indene-1,3-dione |
| 2-[(1-ethyl-2,5-dimethyl-3-pyrrolyl)methylidene]indene-1,3-dione | | 2-[(1-ethyl-2,5-dimethyl-3-pyrrolyl)methylidene]indene-1,3-dione |
| 2-[(3-methyl-2-thiophenyl)methylidene]indene-1,3-dione | | 2-[(3-methyl-2-thiophenyl)methylidene]indene-1,3-dione |
| 2-amino-4-(3-cyclohexen-1-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydrochromene-3-carbonitrile | A member of the class of chromenes that is 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydrochromene carrying additional amino, cyano and 3-cyclohexen-1-yl substituents at positions 2, 3 and 4 respectively. | 2-amino-4-(3-cyclohexen-1-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydrochromene-3-carbonitrile |
| 2-dodecylcyclobutanone | | 2-Dodecylcyclobutanone |
| 2-tetradecylcyclobutanone | | 2-Tetradecylcyclobutanone |
| 2,2-bis(hydroxymethyl)-1-azabicyclo(2,2,2,)octan-3-one | | 2,2-bis(hydroxymethyl)-1-azabicyclo[2.2.2]octan-3-one |
| 2,2'-spirobi[3,6,7,8-tetrahydro-1H-cyclopenta[g]naphthalene]-5,5'-dione | A spiro compound that consists of two units of 1,2,3,6,7,8-hexahydro-5H-cyclopenta[b]naphthalen-5-one fused together at position 2. It is an inhibitor of Hepatitis C virus E2 protein that exhibits inhibitory activity against hepatitis C virus infections. | 2,2'-spirobi[3,6,7,8-tetrahydro-1H-cyclopenta[g]naphthalene]-5,5'-dione |
| 3-methyl-1,2-cyclopentanedione | | 3-Methyl-1,2-cyclopentanedione |
| 3,7-dihydroxytropolone | A cyclic ketone that is tropolone in which the hydrogens at positions 3 and 7 are substituted by hydroxy groups. It is isolated from the soil bacterium Streptomyces tropolofaciens strain K611-97. | 3,7-dihydroxytropolone |
| 4-hydroxy-2-ethyl-5-methyl-3(2h)-furanone | A member of the class of furans that is furan-3(2H)-one carrying additional ethyl, hydroxy and methyl substituents at positions 2, 4 and 5 respectively. A key aroma compound in soy sauce and fish sauce. | 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone |
| 4-hydroxy-5-methyl-3(2h)-furanone | A member of the class of furans that is 5-methyl-2,3-dihydrofuran with a hydroxy group at position 4 and a keto group at position 3. | 4-hydroxy-5-methyl-3-furanone |
| 4-oxoretinol | A retinoid that is all-trans-retinol in which the hydrogens at position 4 have been replaced by an oxo group. | all-trans-4-oxoretinol |
| 6-azathymine | A nucleobase analogue that is thymine in which the CH group at position 6 is replaced by nitrogen. | 6-azathymine |
| 8-isoprostaglandin e2 | A prostanoid that is prostaglandin E2 having inverted stereochemistry at the 8-position. | 8-epi-prostaglandin E2 |
| acridone | A member of the class of acridines that is 9,10-dihydroacridine substituted by an oxo group at position 9. | acridone |
| adefovir | A dimeric naphthopyran with formula C32H26O10, originally isolated from Aspergillus niger. | aurasperone A |
| adonixanthin | A carotenone that consists of beta,beta-caroten-4-one bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'R diastereomer). | adonixanthin |
| allocryptopine | | allocryptopine |
| alloin | A C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9S diastereoisomer). | aloin A |
| alpha bitter acid | An optically active cyclic ketone consisting of 3,5,6-trihydroxycyclohexa-2,4-dien-1-one bearing two 3-methylbut-2-en-1-yl substituents at positions 4 and 6 as well as a 3-methylbutanoyl group at the 2-position. | humulone |
| aromaticin | A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8 and a methylidene group at position 3. Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity. | aromaticin |
| 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 |
| aurone | A simplest memebr of the class of aurones that is 1-benzofuran-3(2H)-one in which both hydrogens at position 2 are substituted by a benzylidene group (the Z-isomer). | aurone |
| benzobicyclon | A carbobicyclic compound that is bicyclo[3.2.1]oct-3-en-2-one which is substituted at positions 3 and 4 by 2-chloro-4-(methylsulfonyl)benzoyl and phenylthio groups, respectively. | 3-[2-chloro-4-(methylsulfonyl)benzoyl]-4-(phenylthio)bicyclo[3.2.1]oct-3-en-2-one |
| beta-dolabrin | | beta-Dolabrin |
| beta-thujaplicin | A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities. | beta-thujaplicin |
| bigelovin | A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity. | bigelovin |
| 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 |
| bromindione | | bromindione |
| ceratamine a | An organic heterobicyclic compound, which is imidazo[4,5-d]azepin-5(6H)-one substituted by a 3,5-dibromo-4-methoxybenzyl group at position 4, a methyl group at position 6 and a methylamino group at position 2. It is an antimitotic alkaloid isolated from the marine sponge Pseudoceratina. | ceratamine A |
| chlordecone | An organochlorine compound with insecticidal activity. | chlordecone |
| civetone | A macrocycle that is cycloheptadecanone with an unsaturation at position 9 (the 9Z-stereoisomer). It has been found in African Civets. | civetone |
| clorindione | | clorindione |
| colchiceine | | Colchiceine |
| colforsin | A labdane diterpenoid isolated from the Indian Coleus plant. | forskolin |
| colforsin daropate | A carboxylic ester resuting from the formal condensation of the carboxy group of N,N-dimethyl-beta-alanine with the 6-hydroxy group of forskolin. It is an adenylate cyclase activator. | colforsin daropate |
| confertin | A pseudoguaianolide that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by an oxo group at position 5, methyl groups at positions 4a and 8 and a methylidene group at position 3. It has been isolated from the aerial parts of Inula hupehensis. | confertin |
| cycloheximide | A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus. | cycloheximide |
| demethylzeylasteral | A carbopolycyclic compound with formula C29H36O6, originally isolated from Tripterygium wilfordii. | demethylzeylasteral |
| deoxynivalenol | A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination. | deoxynivalenol |
| ellagic acid | An organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. | ellagic acid |
| er-086526 | A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage | eribulin |
| ergolide | A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at position 4. It has been isolated from the aerial parts of Inula hupehensis. | ergolide |
| erythromycin | An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively. | erythromycin A |
| erythromycin ethylsuccinate | A erythromycin derivative that is erythromycin A in which the hydroxy group at position 3R is substituted by a (4-ethoxy-4-oxobutanoyl)oxy group. It is used for the treatment of a wide variety of bacterial infections. | erythromycin ethylsuccinate |
| everolimus | A macrocyclic lactone that is rapamycin in which the hydroxy group attached to the cyclohexyl moiety has been converted into the corresponding 2-hydroxyethyl ether. It is an immunosuppressant and antineoplastic agent. | everolimus |
| fluindione | | fluindione |
| fluorescite | A xanthene dye that is highly fluorescent and commonly used as a fluorescent tracer. | fluorescein (acid form) |
| flurithromycin | An erythromycin derivative that is erythromycin A in which the hydrogen attached to the carbon at position 8 (alpha to the ketone carbonyl group) has been replaced by a fluorine. It has been used (generally as the corresponding monoethyl succinate ester) as an antibacterial drug. | flurithromycin |
| fonsecinone a | A dimeric naphthopyran with formula C32H26O10, originally isolated from Aspergillus niger. | fonsecinone A |
| furaneol | A member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits. | 4-hydroxy-2,5-dimethylfuran-3-one |
| gamma-thujaplicin | | gamma-Thujaplicin |
| helenalin | A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). | helenalin |
| integric acid | An eremophilane sesquiterpenoid with anti-HIV-1 activity. It is isolated from Xylaria sp. MF6254. | integric acid |
| isobarbaloin | A C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9R diastereoisomer). | aloin B |
| isophorone | A cyclic ketone, the structure of which is that of cyclohex-2-en-1-one substituted by methyl groups at positions 3, 5 and 5. | isophorone |
| Jasmone | | Jasmone |
| ketotifen | An organic heterotricyclic compound that is 4,9-dihydro-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one which is substituted at position 4 by a 1-methylpiperidin-4-ylidene group. A blocker of histamine H1 receptors with a stabilising action on mast cells, it is used (usually as its hydrogen fumarate salt) for the treatment of asthma, where it may take several weeks to exert its full effect. | ketotifen |
| levobunolol | A cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective beta-adrenergic antagonist used (as its hydrochloride salt) for treatment of glaucoma. | levobunolol |
| liriodenine | An oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities. | liriodenine |
| lycojapodine a | An alkaloid isolated from the club moss Lycopodium japonicum and has been shown to exhibit acetylcholinesterase inhibitory and anti-HIV-1 activity. | lycojapodine A |
| mcb-613 | A cyclic ketone that is 4-ethylcyclohexanone which is substituted by pyridin-3-ylmethylene groups at positions 2 and 6. It is a potent small molecule stimulator of steroid receptor coactivators (SRCs). MCB-613 increases SRCs' interactions with other coactivators and markedly induces ER stress coupled to the generation of reactive oxygen species. Since cancer cells overexpress SRCs and rely on them for growth, MCB-613 can be used to selectively induce excessive stress in cancer cells. | MCB-613 |
| methyl brevifolincarboxylate | An organic heterotricyclic compound that is 1,2,3,5-tetrahydrocyclopenta[c]isochromene substituted by hydroxy groups at positions 7, 8 and 9, oxo groups at positions 3 and 5 and a methoxycarbonyl group at position 1. Isolated from Phyllanthus urinaria and Phyllanthus niruri, it exhibits vasorelaxant activity. | methyl brevifolincarboxylate |
| metribuzin | A member of the class of 1,2,4-triazines that is 1,2,4-triazin-5(4H)-one substituted by an amino group at position 4, tert-butyl group at position 6 and a methylsulfanyl group at position 3. | metribuzin |
| monorden | An antifungal macrolactone antibiotic, obtained from Diheterospora chlamydosporia and Chaetomium chiversii that inhibits protein tyrosine kinase and heat shock protein 90 (Hsp90). | radicicol |
| myricanone | A cyclic ketone isolated from the bark of Morella species and has been shown to exhibit cytotoxic activity against cancer cells. | Myricanone |
| n-deacetyl-n-formylcolchicine | | Gloriosine |
| nile red | An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group. | nile red |
| novofumigatonin | | novofumigatonin |
| 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 |
| oxcarbazepine | A dibenzoazepine derivative, having a carbamoyl group at the ring nitrogen, substituted with an oxo group at C-4 of the azepeine ring which is also hydrogenated at C-4 and C-5. It is a anticholinergic anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy. | oxcarbazepine |
| phencyclone | | 1,3-diphenylcyclopenta[l]phenanthren-2-one |
| 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 |
| platencin | A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the polycyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase. | platencin |
| platensimycin | A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the oxatetracyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase. | platensimycin |
| pronuciferine | An isoquinoline alkaloid isolated from Berberis coletioides. | (+)-pronuciferine |
| pyranonigrin a | A member of the class of pyranopyrroles that is 2-[(1E)-prop-1-en-1-yl]-6,7-dihydropyrano[2,3-c]pyrrole-4,5-dione carrying two additional hydroxy substituents at positions 3 and 7. Originally isolated from Aspergillus niger. | pyranonigrin A |
| pyrazolanthrone | A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase. | anthra[1,9-cd]pyrazol-6(2H)-one |
| retapamulin | | Retapamulin |
| shamixanthone | A pyranoxanthene that is 2,3-dihydropyrano[3,2-a]xanthen-12(1H)-one bearing hydroxy substituents at positions 1 and 11 as well as a prop-1-en-2-yl group at position 2, a methyl substituent at position 5 and a 3,3-dimethylallyl group at position 8. A secondary metabolite produced by Aspergillus nidulans. | shamixanthone |
| sirolimus | A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent. | sirolimus |
| solavetivone | A cyclic ketone derived from spiro[4.5]dec-6-en-8-one by substitution of hydrogens by methyl groups at positions 6 and 10, and by an isopropenyl group at position 2 (the (2R,5S,10R)-diastereoisomer). | solavetivone |
| spectinomycin | A pyranobenzodioxin and antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis. | spectinomycin |
| spiculoic acid a | A carbobicyclic compound that is 2,3,3a,4,5,7a-hexahydro-1H-indene substituted by ethyl groups at positions 3, 4, 5 and 7, a methyl group at position 1, an oxo group at position 2, a 2-phenylethenyl group at position 5 and a carboxy group at position 4 (the 1R,3R,3aS,4S,5R,7aS stereoisomer). Isolated from Plakortis angulospiculatus, it exhibits cytotoxicity against human breast cancer MCF-7 cells. | spiculoic acid A |
| 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 |
| squaric acid dibutyl ester | A cyclic ketone and diether that is a dibutyl ether derivative of squaric acid. | squaric acid dibutyl ester |
| streptogramin a | A macrolide that is (together with pristinamycin IA) a component of pristinamycin, an oral streptogramin antibiotic produced by Streptomyces pristinaespiralis. Pristinamycin exhibits bactericidal activity against Gram positive organisms including methicillin-resistant Staphylococcus aureus. | pristinamycin IIA |
| tembotrione | An aromatic ketone that is 2-benzoylcyclohexane-1,3-dione in which the phenyl group is substituted at positions 2, 3, and 4 by chlorine, (2,2,2-trifluoroethoxy)methyl, and methylsulfonyl groups, respectively. It is a post-emergence herbicide used (particularly in conjunction with the herbicide safener cyprosulfamide) for the control of a wide range of broad-leaved and grassy weeds in corn and other crops. | tembotrione |
| tephrosin | A member of the class of rotenones that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted with geminal methyl groups at position 3, hydroxy group at position 7a and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). It is isolated from the leaves and twigs of Antheroporum pierrei and exhibits antineoplastic and pesticidal activities. | tephrosin |
| tetrabenazine | A benzoquinolizine that is 1,2,3,4,4a,9,10,10a-octahydrophenanthrene in which the carbon at position 10a is replaced by a nitrogen and which is substituted by an isobutyl group at position 2, an oxo group at position 3, and methoxy groups at positions 6 and 7. | 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one |
| tiamulin | A carbotricyclic compound that is pleuromutilin in which the hydroxyacetate group is replaced by a 2-{[2-(diethylamino)ethyl]sulfanyl}acetate group. An antibacterial drug, tiamulin is used in veterinary medicine (generally as its hydrogen fumarate salt) for the treatment of swine dysentery caused by Serpulina hyodysenteriae. | tiamulin |
| tiamulin fumarate (1:1), (3as-(3aalpha,4beta,5alpha,6alpha,8beta,9alpha,9abeta,10s*))-isomer | | Tiamulin fumarate |
| trimethylcolchicinic acid | | 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one |
| triptonide | A diterpene triepoxide that is triptobenzene K in which the acylhydroquinone moiety has undergone oxidation to the corresponding triepoxyketone derivative. It has been isolated from the roots of Tripterygium wilfordii. | triptonide |
| tropodithietic acid | A monocarboxylic acid that is 8,9-dithiabicyclo[5.2.0]nona-1,3,6-triene substituted by a carboxy group at position 2 and an oxo group at position 3. It is a broad spectrum antibiotic produced by the marine bacterium Phaeobacter inhibens that also acts as a signalling molecule at lower concentrations. | tropodithietic acid |
| tropolone | A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii. | tropolone |
| valnemulin | | Valnemulin |
| verbenone | A carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4. | 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one |
| wortmannin | | wortmannin |
| zerumbone | A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia. | zerumbone |