1.02011-09-21 01:58:17 UTC2015-07-21 06:59:46 UTCFDB029602Dihomo-gamma-Linolenoyl ethanolamideDihomo-gamma-Linolenoyl 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](8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide8,11,14-EicosatrienoylethanolamideAnandamide (20.3,n-6)DGLA EADihomo-gamma-linolenoylethanol amideHgleaHomo-g-linolenylethanolamideHomo-gamma-linolenylethanolamideHomo-γ-linolenylethanolamideN-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamideC22H39NO2349.5506349.298079497(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamidehglea150314-34-4CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCOInChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-ULQWKETUACYZLI-QNEBEIHSSA-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-acylethanolaminesOrganic compoundsOrganic nitrogen compoundsOrganonitrogen compoundsAminesAliphatic acyclic compoundsCarbonyl compoundsHydrocarbon derivativesN-acyl aminesOrganic oxidesOrganopnictogen compoundsPrimary alcoholsSecondary carboxylic acid amidesAlcoholAliphatic acyclic compoundCarbonyl groupCarboxamide groupCarboxylic acid derivativeFatty acylFatty amideHydrocarbon derivativeN-acyl-amineN-acylethanolamineOrganic oxideOrganic oxygen compoundOrganooxygen compoundOrganopnictogen compoundPrimary alcoholSecondary carboxylic acid amideN-(long-chain-acyl)ethanolamineN-(polyunsaturated fatty acyl)ethanolamineN-acyl ethanolamides (endocannabinoids)N-acyl ethanolamines (endocannabinoids)Solidlogp6.28logs-6.17solubility2.34e-04 g/llogp5.68pka_strongest_acidic15.45pka_strongest_basic-1.3iupac(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamideaverage_mass349.5506mono_mass349.298079497smilesCCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCOformulaC22H39NO2inchiInChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-inchikeyULQWKETUACYZLI-QNEBEIHSSA-Npolar_surface_area49.33refractivity111.85polarizability44.39rotatable_bond_count17acceptor_count2donor_count2physiological_charge0formal_charge0Specdb::CMs10925Specdb::CMs40136Specdb::CMs137162Specdb::CMs144896Specdb::MsMs290056Specdb::MsMs290057Specdb::MsMs290058Specdb::MsMs329659Specdb::MsMs329660Specdb::MsMs329661Specdb::MsMs2327316Specdb::MsMs2327317Specdb::MsMs2327318Specdb::MsMs2634410Specdb::MsMs2634411Specdb::MsMs2634412HMDB13625#<Reference:0x00005556758a86a0>#<Reference:0x00005556758a84e8>#<Reference:0x00005556758a8330>#<Reference:0x00005556758a8150>