1.0 2011-09-21 01:58:36 UTC 2015-07-21 06:59:47 UTC FDB029623 Prostaglandin D2-1-glyceryl ester 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.1,2 Incubation of 2-AG with cyclooxygenase-2 (COX-2) and specific prostaglandin H2 (PGH2) isomerases in cell cultures and isolated enzyme preparations results in prostaglandin glycerol ester formation.3 The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. In RAW 264.7 cells, PGD2-2-glyceryl ester is the main COX metabolite.3 The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 mixture of the 1- and 2-glyceryl esters in typical aqueous media. While the stability and metabolism of these PG products have been investigated, little is known about their intrinsic biological activity. [HMDB] PGD2-1-glyceryl ester C23H38O7 426.5436 426.26175357 2,3-dihydroxypropyl (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoate 2,3-dihydroxypropyl (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoate CCCCC[C@@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(=O)OCC(O)CO)[C@@H](O)CC1=O InChI=1S/C23H38O7/c1-2-3-6-9-17(25)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-16-18(26)15-24/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,18?,19-,20-,21+/m1/s1 AWSHXGOINMVSGP-CDCWMRKJSA-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 1-monoacylglycerols Carboxylic acid esters Cyclic alcohols and derivatives Cyclic ketones Cyclopentanols Fatty acid esters Fatty alcohols Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Primary alcohols 1-acyl-sn-glycerol Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Cyclic ketone Cyclopentanol Fatty acid ester Fatty alcohol Glycerolipid Hydrocarbon derivative Ketone Monoacylglycerol Monocarboxylic acid or derivatives Monoradylglycerol Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Prostaglandin skeleton Secondary alcohol Solid logp 2.31 ALOGPS logs -3.47 ALOGPS solubility 1.46e-01 g/l ALOGPS logp 2.05 ChemAxon pka_strongest_acidic 13.46 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 2,3-dihydroxypropyl (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoate ChemAxon average_mass 426.5436 ChemAxon mono_mass 426.26175357 ChemAxon smiles CCCCC[C@@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(=O)OCC(O)CO)[C@@H](O)CC1=O ChemAxon formula C23H38O7 ChemAxon inchi InChI=1S/C23H38O7/c1-2-3-6-9-17(25)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-16-18(26)15-24/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,18?,19-,20-,21+/m1/s1 ChemAxon inchikey AWSHXGOINMVSGP-CDCWMRKJSA-N ChemAxon polar_surface_area 124.29 ChemAxon refractivity 116.46 ChemAxon polarizability 48.72 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 40154 Specdb::CMs 136414 Specdb::CMs 144148 Specdb::MsMs 632137 Specdb::MsMs 632138 Specdb::MsMs 632139 Specdb::MsMs 2463063 Specdb::MsMs 2463064 Specdb::MsMs 2463065 Specdb::MsMs 2499371 Specdb::MsMs 2499372 Specdb::MsMs 2499373 Specdb::MsMs 2620742 Specdb::MsMs 2620743 Specdb::MsMs 2620744 Specdb::MsMs 2910161 Specdb::MsMs 2910162 Specdb::MsMs 2910163 HMDB13653