An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
| Member | Definition | Role |
|---|
| (10)-shogaol | | [10]-Shogaol |
| (8)-shogaol | | [8]-Shogaol |
| 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butenone | An enone with a trimethylcyclohexenyl substituent at C-1. | 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enone |
| 1-pentene-3-one | An enone that is pent-1-ene substituted by an oxo group at position 3. | 1-penten-3-one |
| 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one | A diarylheptanoid that is 1,4,6-heptatrien-3-one substituted by 4-hydroxypheny group at positions 1 and 7 respectively. It has been isolated from the rhizomes of Curcuma domestica and Etlingera elatior. | 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one |
| 1,7-bis(4-hydroxyphenyl)hepta-4E-6E-dien-3-one | A diarylheptanoid that is 4E-6E-dien-3-one substituted by 4-hydroxyphenyl group at positions 1 and 7. It has been isolated from the rhizomes of Curcuma kwangsiensis. | 1,7-bis(4-hydroxyphenyl)hepta-4E-6E-dien-3-one |
| 16-dehydropregnenolone | A 3beta-hydroxy-Delta(5)-steroid that is pregnenolone with a double bond between positions 16 and 17. | 16,17-didehydropregnenolone |
| 16-dehydroprogesterone | | 16,17-didehydroprogesterone |
| 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 |
| 3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one | A member of the class of pyridines that is pyridine substituted by a 3-oxo-3-(pyridin-4-yl)prop-1-en-1-yl group at position 3. An inhibitor of PFKFB3 kinase, an enzyme with a key role in glycolysis. | 3PO |
| 3-buten-2-one | A methyl ketone that is butan-2-one with an unsaturation at position 3. | buten-2-one |
| 3'-hydroxyechinenone | A member of the class of carotenone that is echinenone carrying an additional hydroxy substituent at position 3'. Found in cyanobacteria. | 3'-hydroxyechinenone |
| 4-chromone | The simplest member of the class of chromones that is 4H-chromene with an oxo group at position 4. | chromone |
| 4-oxo-(e)-2-hexenal | The enal that is (E)-hex-2-enal substituted with an oxo group at C-4. | (E)-4-oxohex-2-enal |
| 4-oxo-2-nonenal | The enal that is (E)-non-2-enal substituted with an oxo group at C-4. | (E)-4-oxonon-2-enal |
| 4-oxoretinoic acid | A retinoid that consists of all-trans-retinoic acid bearing an oxo substituent at position 4 on the cyclohexenyl ring. | all-trans-4-oxoretinoic acid |
| 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 |
| 4'-epichaetoviridin A | An azaphilone that is the 4'-epimer of chaetoviridin A. It has been isolated from Chaetomium globosum. | 4'-epichaetoviridin A |
| 5-oxo-15-hydroxy-6,8,11,13-eicosatetraenoic acid | An icosanoid that is (6E,8Z,11Z,13E)-icosatetraenoic acid substituted at positions 5 and 15 by oxo and hydroxy groups respectively. | (6E,8Z,11Z,13E,15S)-15-hydroxy-5-oxoicosatetraenoic acid |
| 6-deacetylnimbin | A limonoid that is nimbin in which the acetyloxy group at position 6 is replaced by a hydroxy hroup. It has been isolated from Azadirachta indica. | 6-deacetylnimbin |
| 6-dehydrotestosterone | A 17beta-hydroxy steroid that is testosterone that contains an additional double bond between positions 6 and 7. | 6-dehydrotestosterone |
| 7-deacetylgedunin | A limonoid that is the 7-deacetyl derivative of gedunin. It has been isolated from Azadirachta indica. | 7-deacetylgedunin |
| 9-oxo-10,12-octadecadienoic acid | An oxooctadecadienoic acid that consists of 10E,12E-octadecadienoic acid with the oxo substituent located at position 9. | 9-oxo-10E,12E-ODE |
| albaflavenone | A carbotricyclic compound that is (+)-epi-isozizaene in which the hydrogens at position 5 have been replaced by an oxo group. | albaflavenone |
| alpha-ionone | | alpha-ionone |
| alpha-irone | A methyl ketone that is alpha-ionone in which a hydrogen at position 5 of the cyclohex-2-en-1-yl ring is substituted by a methyl group. | alpha-irone |
| antroquinonol d | An enone that is cyclohex-2-en-1-one substituted by a hydroxy group at position 4, methoxy groups at positions 2 and 3, a methyl group at position 6 and a (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl group at position 5 (the 4R,5R,6R stereoisomer). It is isolated from the solid-state fermented mycelium of the fungus Antrodia camphorata and has been found to exhibit potent cytotoxicity against a number of human cancer cell lines. However, a synthesis-enabled biological re-examination published in 2016, revealed minimal in vitro and in vivo antitumour activity in preclinical models. | antroquinonol |
| ar-turmerone | A sesquiterpenoid that is 2-methylhept-2-en-4-one substituted by a 4-methylphenyl group at position 6. It has been isolated from Peltophorum dasyrachis. | (+)-(S)-ar-turmerone |
| 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 |
| australifungin | A carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl group at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activity by interfering with the fungal lipid metabolism. | australifungin |
| beclomethasone dipropionate | A steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions. | beclomethasone dipropionate |
| beta-apo-13-carotenone | An apo carotenoid compound arising from oxidative degradation of the beta,beta-carotene skeleton at the 13-position. | 13-apo-beta-carotenone |
| beta-damascenone | A cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group. | beta-damascenone |
| biliatresone | A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted at positions 5 by a 2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl group and at positions 4 and 6 by methoxy groups. A very rare type of isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera (red crumbweed) and D. littoralis, the enone moiety is particularly reactive, undergoing ready Michael addition of water and methanol. Biliatresone has been found to cause extrahepatic biliary atresia (obliteration or discontinuity of the extrahepatic biliary system, resulting in obstruction to bile flow) in a zebrafish model. | biliatresone |
| bisdemethoxycurcumin | A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups. | bisdemethoxycurcumin |
| canthin-6-one | An indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6. | canthin-6-one |
| chaetoviridin a | An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. Isolated from Chaetomium globosum, it exhibits natifungal activity against plant pathogenic fungi. | chaetoviridin A |
| chaetoviridin E | An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a methyl group at position 6a, a 2-methylbut-2-enoyl group at position 9 and a 3-methylpent-1-en-1-yl group at position 3. It has been isolated from Chaetomium globosum. | chaetoviridin E |
| curcumin | A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa. | curcumin |
| cyclopentenone | An enone that is cyclopentanone having a C=C double bond at position 2. | 2-cyclopenten-1-one |
| demethoxycurcumin | A beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior. | demethoxycurcumin |
| 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 |
| drymaritin | An indole alkaloid that is canthin-6-one substituted by a methoxy group at position 4. Isolated from the whole plants of Drymaria diandra, it exhibits anti-HIV activity. | drymaritin |
| elloramycin | A member of the class of tetracenomycins that is 8-demethyltetracenomycin C in which the hydroxyl hydrogens at position 8 and 10 a are replaced by a 2,3,4-tri-O-methyl-alpha-L-rhamnosyl and methyl groups respectively. | elloramycin A |
| eurycomanone | A quassinoid isolated from Eurycoma longifolia and has been shown to exhibit antineoplastic and antimalarial activties. | eurycomanone |
| gedunin | A pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata. | gedunin |
| glycyrrhetyl 3-monoglucuronide | A triterpenoid saponin that is the 3-O-beta-glucuronide of glycyrrhetic acid. It is a metabolite of glycyrrhizin contained in licorice and potentially a causative agent in the pathogenesis of pseudoaldosteronism. | glycyrrhetic acid 3-O-glucuronide |
| glycyrrhizic acid | A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid. | glycyrrhizinic acid |
| hypothemycin | A macrolide that is isolated from the cultured broth of Hypomyces subiculosus and shows antifungal activity and inhibits the growth of some human cancer cells. | hypothemycin |
| INDY | A member of the class of benzothiazoles that is 2,3-dihydro-1,3-benzothiazole substituted by 2-oxopropylidene, ethyl, and hydroxy groups at positions 2, 3 and 5, respectively. It is an ATP-competitive inhibitor of Dyrk1A and Dyrk1B (IC50 of 0.24 muM and 0.23 muM, respectively). | INDY |
| integric acid | An eremophilane sesquiterpenoid with anti-HIV-1 activity. It is isolated from Xylaria sp. MF6254. | integric acid |
| 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 |
| lactucin | An azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 respectively (the 3aR,4S,9aS,9bR-diastereomer). Found in chicory. | lactucin |
| 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 2-cyano-3-(dimethylamino)acrylate | | Methyl 2-cyano-3-(dimethylamino)acrylate |
| methyltestosterone | A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position. | methyltestosterone |
| methymycin | A twelve-membered macrolide antibiotic that is biosynthesised by Streptomyces venezuelae. | methymycin |
| monascorubrin | | monascorubrin |
| monorden | An antifungal macrolactone antibiotic, obtained from Diheterospora chlamydosporia and Chaetomium chiversii that inhibits protein tyrosine kinase and heat shock protein 90 (Hsp90). | radicicol |
| mycaminosyltylonolide | A macrolide antibiotic that is tylonolide having a beta-D-mycaminosyl residue attached at position 5. | 5-O-mycaminosyltylonolide |
| narbomycin | A macrolide antibiotic that is narbonolide having a 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residue attached at position 6. It is biosynthesised by Streptomyces venezuelae. | narbomycin |
| neomethymycin | A twelve-membered macrolide antibiotic that is biosynthesised by Streptomyces venezuelae. | neomethymycin |
| nimbin | A limonoid found in Azadirachta indica. | nimbin |
| nootkatone | A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer). | (+)-nootkatone |
| oridonin | An organic heteropentacyclic compound and ent-kaurane diterpenoid with formula C20H28O6 isolated from the leaves of the medicinal herb Rabdosia rubescens. | oridonin |
| 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 |
| petasin | An enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-ol. | petasin |
| pf-06687252 | An azabicycloalkane that is (1R,4R)-2,5-diazabicyclo[2.2.1]heptane which is substituted at position 2 by a 3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl group and at position 5 by a pyridin-2-yl group. It is a potent and selective inhibitor of polybromo 1 (Kd = 48 nM), SMARCA2 and SMARCA4 (Kd = 89 nM) bromodomains. | PFI-3 |
| 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 |
| physalin b | A physalin with antimalarial, antitumour and antimicrobial activities isolated from Physalis angulata. | physalin B |
| physalin d | A physalin with antimalarial and antimycobacterial activities isolated from Physalis angulata. | physalin D |
| physalin f | A physalin with antimalarial and antitumour activities isolated from Physalis angulata. | physalin F |
| physalin g | A physalin with antimalarial activity isolated from Physalis angulata. | physalin G |
| picromycin | A macrolide antibiotic that is biosynthesised by Streptomyces venezuelae. | pikromycin |
| pramanicin | | Pramanicin |
| protylonolide | A 16-membererd macrolide that is the aglycone of the antibiotic 5-O-beta-D-mycaminosyltylactone. | tylactone |
| resiniferatoxin | A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1). | resiniferatoxin |
| rosaramicin | A macrolide antibiotic with activity against Neisseria gonorrhoeae, Chlamydia trachomatis, Ureaplasma urealyticum and Mycoplasma hominis. | rosaramicin |
| rottlerin | A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis. | rottlerin |
| sch 642305 | A macrocyclic lactone isolated from the fermentation broth of the fungal culture Penicillium verrucosum and has been shown to exhibit inhibitory activity against bacterial DNA primase enzyme. | sch 642305 |
| scytonemin | A ring assembly obtained by 1,1'-coupling of two molecules of (3E)-3-[(4-hydroxyphenyl)methylidene]cyclopenta[b]indol-2(3H)-one. A UV-screening molecule produced by many strains of cyanobacteria. | scytonemin |
| shogaol | | [6]-Shogaol |
| simalikalactone D | A quassinoid isolated from Quassia amara and Quassia africana. It has been shown to exhibit antimalarial, cytotoxic and antiviral activities. | simalikalactone D |
| testosterone 17-glucosiduronate | A steroid glucosiduronic that is testosterone carrying a glucosiduronic acid residue at position 17. | testosterone 17-glucosiduronic acid |
| tetrahydroxycurcumin | A beta-diketone that is curcumin in which the two methoxy groups have been replaced by hydroxy groups. It is a metabolite of curcumin. | tetrahydroxycurcumin |
| tilmicosin | A macrolide antibiotic with formula C46H80N2O13. It is used for the treatment of respiratory disease in cattle at high risk of developing bovine respiratory disease associated with Mannheimia haemolytica. | tilmicosin |
| tubocapsanolide a | A withanolide that is 5beta,6beta:16alpha,17alpha-diepoxywitha-2,24-dienolide substituted by a hydroxy group at position 4 and an oxo group at position 1. Isolated from Tubocapsicum anomalum, it exhibits cytotoxic activity. | tubocapsanolide A |
| tylosin | A macrolide antibiotic that is tylonolide having mono- and diglycosyl moieties attached to two of its hydroxy groups. It is found naturally as a fermentation product of Streptomyces fradiae. | tylosin |
| 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 |
| 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 |
| withaferin a | A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity. | withaferin A |
| 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 |
| xenovulene a | A sesquiterpenoid based on a humulene skeleton. It is isolated from Sarocladium strictum and has been shown to exhibit inhibitory activity against GABA receptor. | xenovulene A |