1.0 2010-04-08 22:04:58 UTC 2025-11-18 22:31:13 UTC FDB001433 3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid, also known as opc-8:0, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid is considered to be an octadecanoid lipid molecule. 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid can be found in common wheat, corn, eggplant, and flaxseed, which makes 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid a potential biomarker for the consumption of these food products. OPC-8:0 C18H30O3 294.429 294.219494826 8-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]octanoic acid 8-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]octanoic acid 204135-86-4 CC\C=C/C[C@H]1[C@@H](CCCCCCCC(O)=O)CCC1=O InChI=1S/C18H30O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,15-16H,2,4-6,8-14H2,1H3,(H,20,21)/b7-3-/t15-,16-/m0/s1 BZXZFDKIRZBJEP-JMTMCXQRSA-N belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Prostaglandins and related compounds Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic homomonocyclic compounds Carboxylic acids Cyclic ketones Hydrocarbon derivatives Medium-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic ketone Hydrocarbon derivative Ketone Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton 12-oxophytodienoic acid metabolites logp 5.20 ALOGPS logs -5.04 ALOGPS solubility 2.69e-03 g/l ALOGPS logp 5.08 ChemAxon pka_strongest_acidic 4.72 ChemAxon pka_strongest_basic -7.4 ChemAxon iupac 8-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]octanoic acid ChemAxon average_mass 294.429 ChemAxon mono_mass 294.219494826 ChemAxon smiles CC\C=C/C[C@H]1[C@@H](CCCCCCCC(O)=O)CCC1=O ChemAxon formula C18H30O3 ChemAxon inchi InChI=1S/C18H30O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,15-16H,2,4-6,8-14H2,1H3,(H,20,21)/b7-3-/t15-,16-/m0/s1 ChemAxon inchikey BZXZFDKIRZBJEP-JMTMCXQRSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 86.16 ChemAxon polarizability 35.91 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1086906 Specdb::EiMs 3421 Specdb::NmrOneD 270978 Specdb::NmrOneD 270979 Specdb::NmrOneD 270980 Specdb::NmrOneD 270981 Specdb::NmrOneD 270982 Specdb::NmrOneD 270983 Specdb::NmrOneD 270984 Specdb::NmrOneD 270985 Specdb::NmrOneD 270986 Specdb::NmrOneD 270987 Specdb::NmrOneD 270988 Specdb::NmrOneD 270989 Specdb::NmrOneD 270990 Specdb::NmrOneD 270991 Specdb::NmrOneD 270992 Specdb::NmrOneD 270993 Specdb::NmrOneD 270994 Specdb::NmrOneD 270995 Specdb::NmrOneD 270996 Specdb::NmrOneD 270997 Specdb::MsMs 63270 Specdb::MsMs 63271 Specdb::MsMs 63272 Specdb::MsMs 120201 Specdb::MsMs 120202 Specdb::MsMs 120203 Specdb::MsMs 3597355 Specdb::MsMs 3597356 Specdb::MsMs 3597357 Specdb::MsMs 3598274 Specdb::MsMs 3598275 Specdb::MsMs 3598276 Common wheat Type 1 specific Triticum aestivum 4565 Corn Type 1 specific Zea mays 4577 Eggplant Type 1 specific Solanum melongena 4111 Flaxseed Type 1 specific Linum usitatissimum 4006