Natural and synthetic compounds containing alternating carbonyl and methylene groups ('beta-polyketones'), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations, etc. Considered by many to be synonymous with the less frequently used terms acetogenins and ketides.
| Member | Definition | Role |
|---|
| 6-[(3E,5E,7S)-5,7-dimethyl-2-oxonona-3,5-dienyl]-2,4-dihydroxy-3-methylbenzaldehyde | | 6-[(3E,5E,7S)-5,7-dimethyl-2-oxonona-3,5-dienyl]-2,4-dihydroxy-3-methylbenzaldehyde |
| 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 |
| aclarubicin | An anthracycline antibiotic that is produced by Streptomyces galilaeus and also has potent antineoplastic activity. | aclacinomycin A zwitterion; aclacinomycin A |
| annomontacin | | Annomutacin |
| aspalathin | A member of the class of dihydrochalcones that is the 2-C-beta-D-glucopyranide of phloroglucinol and which is substituted at position 4 by a 3-(3,4-dihydroxyphenyl)propanoyl group. A metabolite of red bush, Aspalathus linearis (and present in the herbal tea made from the leaves), aspalathin exhibits significant hypoglycemic activity. | aspalathin |
| 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 |
| averufin | An organic heteropentacyclic compound that is 3,4,5,6-tetrahydro-2H-2,6-epoxyanthra[2,3-b]oxocine-8,13-dione substituted at position 2 by a methyl group and at positions 7, 9 and 11 by hydroxy groups (the S,S-diastereomer) | (1'S,5'S)-averufin |
| bacillaene | A polyene antibiotic obtained from Bacillus subtilis 168 that is active against a broad spectrum of bacteria. It is notoriously unstable. | bacillaene |
| benanomicin b | A member of the class of pradimicins that is isolated from the cultured broth of Actinomadura hibisca No. P157-2 (ATCC 53557). | pradimicin C |
| cannabidiolic acid | A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a 3-p-mentha-1,8-dien-3-yl (limonene) group. | cannabidiolic acid |
| cannabigerolic acid | A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. | cannabigerolic acid |
| cefadroxil | | Uvaricin |
| colibactin | A member of the class of 1,3-thiazoles that comprises of two units of 2-[(2-{6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl}acetamido)methyl]-1,3-thiazole-4-carboxylic acid linked together via the formal condensation of the carboxy groups. It is a secondary metabolite produced by certain strains of bacteria found in the human gut such as Escherichia coli. It has the ability to bind covalently to DNA and is strongly associated with colorectal cancer. | colibactin |
| delta(9)-tetrahydrocannabinolic acid | A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. | Delta(9)-tetrahydrocannabinolic acid |
| depudecin | A polyketide obtained from the fungus Alternaria brassicicola and having a highly unusual structure of an 11-carbon chain containing two epoxides and six stereogenic centres. It is an inhibitor of histone deacetylase (HDAC) both in vivo and in vitro and also exhibits anti-angiogenic activity. | depudecin |
| dronabinol | A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy. | Delta(9)-tetrahydrocannabinol |
| fostriecin | A structurally unique, naturally-occurring phosphate monoester isolated from the soil bacterium Streptomyces pulveraceus. It inhibits DNA topoisomerase II as well as several protein phosphatase including PP2A and PPA4, and exhibits potent antitumor activity against several cancer cell lines. | fostriecin |
| fr 900848 | A polyketide that is 5'-amino-5'-deoxy-3,4,5,6-tetrahydrouridine in which one of the hydrogens of the amino group is substituted by a (1E,3E)-1-[(1R,1'R,1''R,1'''R,2S,2'R,2''R,2'''S)-2'''-{(E)-2-[(1R,2R)-2-methylcyclopropyl]ethenyl}[1,1':2',1'':2'',1'''-quater(cyclopropan)]-2-yl]-5-oxopenta-1,3-dien-5-yl group. It is a metabolite isolated from the bacterium, Streptoverticillium fervens and targets the catalytic subunit of the fungal UDP-glycosyltransferase, the first step in the biosynthesis of glycosylphosphatidylinositol (GPI) anchors. It exhibits broad spectrum antifungal activity against several pathogenic fungi including Mucorales. | jawsamycin |
| 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 |
| l 154819 | A polyketide obtained by hydrolysis of the pyranone ring of lovastatin. | mevinolinic acid |
| lovastatin | A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). | lovastatin |
| 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 |
| mevastatin | A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals. | mevastatin |
| ml 236a | A carbobicyclic compound that is ML-236C substituted by a hydroxy group at position 8S. It is a fungal metabolite isolated from Penicillium citrinum and exhibits anticholesteremic activity. | compactin diol lactone |
| monacolin j | A polyketide that is monacolin L bearing an additional hydroxy substituent at position 8. | monacolin J |
| monacolin l | A polyketide that is 1-ethyl-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalene in which one of the methyl hydrogens from the ethyl group is replaced by a 4-hydroxy-6-ketopyran-2-yl group. | monacolin L |
| monascin | An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours. | monascin |
| monascorubrin | | monascorubrin |
| mucocin | | Mucocin |
| murisolin | | Murisolin |
| norsolorinic acid | A polyketide that is anthraquinone bearing four hydroxy substituents at positions 1, 3, 6 and 8 as well as a hexanoyl substituent at position 2. | norsolorinic acid |
| olivetolic acid | A member of the class of benzoic acids that is salicylic acid in which the hydrogens ortho- and para- to the carboxy group are replaced by a pentyl and a hydroxy group, respectively. | olivetolic acid |
| pederin | A polyketide and carboxamide produced by a (Pseudomonas) bacterial endosymbiont of certain rove beetles (genus Paederus). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent. | pederin |
| pradimicin b | A member of the class of prodimicins that is isolated from the cultured broth of Actinomadura hibisca No. P157-2 (ATCC 53557). | pradimicin B |
| pyoluteorin | A member of the class of resorcinols that is resorcinol in which the hydrogen at position 2 is replaced by a 4,5-dichloro-1H-pyrrole-2-carbonyl group. It is a natural product found in Pseudomonas fluorescens which exhibits antibacterial properties and is a strong inducer of caspase-3-dependent apoptosis. | pyoluteorin |
| rubrofusarin | A member of the class of benzochromenones that is benzo[g]chromen-4-one carrying two additional hydroxy substituents at positions 5 and 6 as well as methyl and methoxy substituents at positions 2 and 8 respectively. An orange polyketide pigment that is a common intermediate in many different fungal biosynthetic pathways. | rubrofusarin |
| rubrofusarin B | A benzochromenone that is rubrofusarin in which the hydroxy group at position 6 has been converted to the corresponding methyl ether. | rubrofusarin B |
| salinomycin | | Salinomycin |
| squalestatin 1 | A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. | zaragozic acid A |
| squamocin | | Squamocin |
| trilobacin | A polyketide isolated from the bark of Asimina triloba. It has been shown to exhibit cytotoxicity in the NCI human tumor cell line screen. | trilobacin |
| troleandomycin | A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug. | troleandomycin |
| uvaretin | A member of the class of dihydrochalcones that is 1,3-diphenylpropan-1-one in which the phenyl group that is bonded to the carbonyl group is substituted by hydroxy groups at positions 2 and 4, an o-hydroxybenzyl group at position 3, and a methoxy group at position 6. A cytotoxic natural product found particularly in Uvaria acuminata and Uvaria chamae. | uvaretin |
| visnagin | A furanochromone that is furo[3,2-g]chromen-5-one which is substituted at positions 4 and 7 by methoxy and methyl groups, respectively. Found in the toothpick-plant, Ammi visnaga. | visnagin |
| zaragozic acid c | A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. | zaragozic acid C |