1.0 2011-09-21 01:58:21 UTC 2025-11-19 02:57:57 UTC FDB029606 PGD2 ethanolamide PGD2 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] PGD2 EA Prostaglandin D2 ethanolamide prostaglanding D2 ethaolamide Prostamide D2 C22H37NO5 395.54 395.267173295 (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide PGD2-EA 398138-28-8 CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(=O)NCCO)[C@@H](O)CC1=O 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/h4,7,12-13,17-20,24-26H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,20-/m0/s1 KEYDJKSQFDUAGF-YIRKRNQHSA-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 N-acylethanolamine Prostaglandins monocarboxylic acid amide logp 2.62 ALOGPS logs -3.80 ALOGPS solubility 6.26e-02 g/l ALOGPS logp 1.95 ChemAxon pka_strongest_acidic 13.96 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide ChemAxon average_mass 395.54 ChemAxon mono_mass 395.267173295 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(=O)NCCO)[C@@H](O)CC1=O 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/h4,7,12-13,17-20,24-26H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,20-/m0/s1 ChemAxon inchikey KEYDJKSQFDUAGF-YIRKRNQHSA-N ChemAxon polar_surface_area 106.86 ChemAxon refractivity 112.45 ChemAxon polarizability 46.39 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 40140 Specdb::CMs 65323 Specdb::CMs 153056 Specdb::MsMs 1238302 Specdb::MsMs 1238303 Specdb::MsMs 1238304 Specdb::MsMs 1353751 Specdb::MsMs 1353752 Specdb::MsMs 1353753 Specdb::MsMs 2761153 Specdb::MsMs 2761154 Specdb::MsMs 2761155 Specdb::MsMs 2945304 Specdb::MsMs 2945305 Specdb::MsMs 2945306 HMDB13629