1.0 2011-09-21 01:58:21 UTC 2018-05-28 18:38:34 UTC FDB029607 20-HETE ethanolamide 20-HETE 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] 20-HETE EA 20-HETE-EA 20-HETE-ethanolamine 20-hydroxy AEA 20-hydroxy arachidonoyl ethanolamide 20-hydroxyepoxyeicosatrienoate 20-hydroxyepoxyeicosatrienoic acid 20-hydroxyepoxyeicosatrienoic acid ethanolamide C22H37NO3 363.5341 363.277344055 (5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide 20-hete-EA 942069-11-6 OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO InChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10- QRMZDMUHHZLRMH-DTLRTWKJSA-N belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. N-acylethanolamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives N-acyl amines Organic oxides Organopnictogen compounds Primary alcohols Secondary carboxylic acid amides Alcohol Aliphatic acyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty amide Hydrocarbon derivative N-acyl-amine N-acylethanolamine Organic oxide Organic oxygen compound Organooxygen compound Organopnictogen compound Primary alcohol Secondary carboxylic acid amide N-acyl ethanolamines (endocannabinoids) Solid logp 4.88 ALOGPS logs -5.11 ALOGPS solubility 2.81e-03 g/l ALOGPS logp 3.88 ChemAxon pka_strongest_acidic 15.44 ChemAxon pka_strongest_basic -1.2 ChemAxon iupac (5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide ChemAxon average_mass 363.5341 ChemAxon mono_mass 363.277344055 ChemAxon smiles OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO ChemAxon formula C22H37NO3 ChemAxon inchi InChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10- ChemAxon inchikey QRMZDMUHHZLRMH-DTLRTWKJSA-N ChemAxon polar_surface_area 69.56 ChemAxon refractivity 114.89 ChemAxon polarizability 44.19 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 13073 Specdb::CMs 40141 Specdb::CMs 147563 Specdb::MsMs 294727 Specdb::MsMs 294728 Specdb::MsMs 294729 Specdb::MsMs 335527 Specdb::MsMs 335528 Specdb::MsMs 335529 Specdb::MsMs 2720877 Specdb::MsMs 2720878 Specdb::MsMs 2720879 Specdb::MsMs 2958474 Specdb::MsMs 2958475 Specdb::MsMs 2958476 HMDB13630 #<Reference:0x000055ce316fe438> #<Reference:0x000055ce316fe1e0> #<Reference:0x000055ce316fdfd8> #<Reference:0x000055ce316fde20>