1.0 2011-09-21 01:52:53 UTC 2017-04-03 04:56:44 UTC FDB029268 Prostaglandin PGE2 glyceryl ester GE2 glycerol ester is a COX-2 oxidative metabolite of 2-arachidonoyl glycerol, modulates inhibitory synaptic transmission in mouse hippocampal neurons 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain,1 and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.2 Incubation of 2-AG with 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. The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 2:1-glyceryl ester mixture in typical aqueous media. While the stability and metabolism of these prostaglandin products has been investigated,4 little is known about their intrinsic biological activity. Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB] 2-PGE(,2)-G PGE(,2) glyceryl ester PGE(,2)-G Prostaglandin PGE(,2)-2-glyceryl ester C23H38O7 426.5436 426.26175357 1,3-dihydroxypropan-2-yl (5Z)-7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoate 1,3-dihydroxypropan-2-yl (5Z)-7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoate 122-60-1 CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](O)CC(=O)[C@H]1C\C=C/CCCC(=O)OC(CO)CO InChI=1S/C23H38O7/c1-2-3-6-9-17(26)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-18(15-24)16-25/h4,7,12-13,17-20,22,24-26,28H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,19-,20-,22-/m0/s1 HJWDPZIOTMUWRW-KSGZNQJUSA-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 2-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 2-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 2.24 ALOGPS logs -3.41 ALOGPS solubility 1.66e-01 g/l ALOGPS logp 2.05 ChemAxon pka_strongest_acidic 14.13 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 1,3-dihydroxypropan-2-yl (5Z)-7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-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](O)CC(=O)[C@H]1C\C=C/CCCC(=O)OC(CO)CO ChemAxon formula C23H38O7 ChemAxon inchi InChI=1S/C23H38O7/c1-2-3-6-9-17(26)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-18(15-24)16-25/h4,7,12-13,17-20,22,24-26,28H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,19-,20-,22-/m0/s1 ChemAxon inchikey HJWDPZIOTMUWRW-KSGZNQJUSA-N ChemAxon polar_surface_area 124.29 ChemAxon refractivity 116.46 ChemAxon polarizability 48.39 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 40046 Specdb::CMs 146809 Specdb::MsMs 655675 Specdb::MsMs 655676 Specdb::MsMs 655677 Specdb::MsMs 2302317 Specdb::MsMs 2302318 Specdb::MsMs 2302319 Specdb::MsMs 2701780 Specdb::MsMs 2701781 Specdb::MsMs 2701782 Specdb::MsMs 3066440 Specdb::MsMs 3066441 Specdb::MsMs 3066442 Specdb::MsMs 3109986 Specdb::MsMs 3109987 Specdb::MsMs 3109988 HMDB13045