1.0 2011-09-21 01:58:20 UTC 2015-07-21 06:59:46 UTC FDB029605 PGF2a ethanolamide PGF2a ethanolamide is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337, 12056855, 12560208, 11997249) [HMDB] N-(9S,11R,15S-trihydroxy-5Z,13E-prostadienoyl)-ethanolamine PGF2a EA PGF2alpha-EA Prostaglandin F2alpha-EA prostaglanding F2a ethanolamideN-(8Z,11Z,14Z-icosatrienoyl)-ethanolamide C22H39NO5 397.5488 397.282823363 (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(=O)NCCO InChI=1S/C22H39NO5/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/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4+,13-12+/t17-,18+,19+,20-,21+/m0/s1 XCVCLIRZZCGEMU-FPLRWIMGSA-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 Carbonyl compounds Cyclic alcohols and derivatives 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 Cyclopentanol Fatty amide Hydrocarbon derivative 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 2.09 ALOGPS logs -3.56 ALOGPS solubility 1.08e-01 g/l ALOGPS logp 1.34 ChemAxon pka_strongest_acidic 14.45 ChemAxon pka_strongest_basic -0.32 ChemAxon iupac (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide ChemAxon average_mass 397.5488 ChemAxon mono_mass 397.282823363 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(=O)NCCO ChemAxon formula C22H39NO5 ChemAxon inchi InChI=1S/C22H39NO5/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/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4+,13-12+/t17-,18+,19+,20-,21+/m0/s1 ChemAxon inchikey XCVCLIRZZCGEMU-FPLRWIMGSA-N ChemAxon polar_surface_area 110.02 ChemAxon refractivity 113.48 ChemAxon polarizability 47.34 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 5 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18261 Specdb::CMs 40139 Specdb::CMs 131091 Specdb::CMs 138825 Specdb::MsMs 306493 Specdb::MsMs 306494 Specdb::MsMs 306495 Specdb::MsMs 350155 Specdb::MsMs 350156 Specdb::MsMs 350157 Specdb::MsMs 2266992 Specdb::MsMs 2266993 Specdb::MsMs 2266994 Specdb::MsMs 3071220 Specdb::MsMs 3071221 Specdb::MsMs 3071222 HMDB13628 53081 #<Reference:0x000055ce3231dae8> #<Reference:0x000055ce3231d930> #<Reference:0x000055ce3231d750> #<Reference:0x000055ce3231d548>