1.0 2011-09-21 01:53:16 UTC 2017-03-11 23:01:02 UTC FDB029286 Stearoylethanolamide Stearoylethanolamide 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] Stearic acid monoethanolamide Stearoyl ethanolamide C20H41NO2 327.545 327.313729561 N-(2-hydroxyethyl)octadecanamide stearoyl-ethanolamine 111-57-9 CCCCCCCCCCCCCCCCCC(=O)NCCO InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23) OTGQIQQTPXJQRG-UHFFFAOYSA-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-(long-chain-acyl)ethanolamine N-(saturated fatty acyl)ethanolamine N-acyl ethanolamines (endocannabinoids) Solid logp 6.67 ALOGPS logs -5.97 ALOGPS solubility 3.54e-04 g/l ALOGPS logp 5.87 ChemAxon pka_strongest_acidic 15.46 ChemAxon pka_strongest_basic -0.33 ChemAxon iupac N-(2-hydroxyethyl)octadecanamide ChemAxon average_mass 327.545 ChemAxon mono_mass 327.313729561 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)NCCO ChemAxon formula C20H41NO2 ChemAxon inchi InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23) ChemAxon inchikey OTGQIQQTPXJQRG-UHFFFAOYSA-N ChemAxon polar_surface_area 49.33 ChemAxon refractivity 99.3 ChemAxon polarizability 44.34 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15495 Specdb::CMs 40052 Specdb::CMs 170864 Specdb::MsMs 73863 Specdb::MsMs 73864 Specdb::MsMs 73865 Specdb::MsMs 133113 Specdb::MsMs 133114 Specdb::MsMs 133115 Specdb::MsMs 2355909 Specdb::MsMs 2355910 Specdb::MsMs 2355911 Specdb::MsMs 2607228 Specdb::MsMs 2607229 Specdb::MsMs 2607230 Specdb::NmrOneD 261108 Specdb::NmrOneD 261109 Specdb::NmrOneD 261110 Specdb::NmrOneD 261111 Specdb::NmrOneD 261112 Specdb::NmrOneD 261113 Specdb::NmrOneD 261114 Specdb::NmrOneD 261115 Specdb::NmrOneD 261116 Specdb::NmrOneD 261117 Specdb::NmrOneD 261118 Specdb::NmrOneD 261119 Specdb::NmrOneD 261120 Specdb::NmrOneD 261121 Specdb::NmrOneD 261122 Specdb::NmrOneD 261123 Specdb::NmrOneD 261124 Specdb::NmrOneD 261125 Specdb::NmrOneD 261126 Specdb::NmrOneD 261127 HMDB13078 #<Reference:0x000055ce31eff768> #<Reference:0x000055ce31eff5b0> #<Reference:0x000055ce31eff3f8> #<Reference:0x000055ce31eff240>