1.0 2011-09-21 01:52:49 UTC 2015-07-21 06:59:40 UTC FDB029263 Prostaglandin E2 ethanolamide prostaglandin E2 ethanolamide is the major prostanoid product derived from anandamide. Incubation of anandamide with lysates and the intact cell line expressing COX-2 but not that of COX-1 produced prostaglandin E2 ethanolamide. This reaction demonstrates the existence of a COX-2-mediated pathway for anandamide metabolism, and the metabolites formed represent a novel class of prostaglandins. 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] PGE2EA C22H37NO5 395.5329 395.267173299 (5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide (5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)NCCO InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-19,21,24-25,27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,21-/m0/s1 GKKWUSPPIQURFM-XXHBNTRVSA-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 Cyclic alcohols and derivatives Cyclic ketones Cyclopentanols Hydrocarbon derivatives N-acyl amines N-acylethanolamines Organic oxides Organopnictogen compounds Primary alcohols Secondary carboxylic acid amides Alcohol Aliphatic homomonocyclic compound Alkanolamine Carbonyl group Carboxamide group Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclopentanol Fatty amide Hydrocarbon derivative Ketone N-acyl-amine N-acylethanolamine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary alcohol Prostaglandin skeleton Secondary alcohol Secondary carboxylic acid amide Solid logp 2.62 ALOGPS logs -3.80 ALOGPS solubility 6.21e-02 g/l ALOGPS logp 1.95 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -0.32 ChemAxon iupac (5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide ChemAxon average_mass 395.5329 ChemAxon mono_mass 395.267173299 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)NCCO ChemAxon formula C22H37NO5 ChemAxon inchi InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-19,21,24-25,27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,21-/m0/s1 ChemAxon inchikey GKKWUSPPIQURFM-XXHBNTRVSA-N ChemAxon polar_surface_area 106.86 ChemAxon refractivity 112.45 ChemAxon polarizability 46.17 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17986 Specdb::CMs 40041 Specdb::CMs 159977 Specdb::MsMs 305845 Specdb::MsMs 305846 Specdb::MsMs 305847 Specdb::MsMs 349339 Specdb::MsMs 349340 Specdb::MsMs 349341 Specdb::MsMs 2687648 Specdb::MsMs 2687649 Specdb::MsMs 2687650 Specdb::MsMs 2993924 Specdb::MsMs 2993925 Specdb::MsMs 2993926 HMDB13038