1.02011-09-21 00:24:24 UTC2019-11-26 03:21:07 UTCFDB0230828,11,14-Eicosatrienoic acid8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids [HMDB](8Z,11Z,14Z)-Icosatrienoate(8Z,11Z,14Z)-Icosatrienoic acid(Z,Z,Z)-8,11,14-Eicosatrienoate(Z,Z,Z)-8,11,14-Eicosatrienoic acid(Z,Z,Z)-8,11,14-Icosatrienoate(Z,Z,Z)-8,11,14-Icosatrienoic acid(Z,Z,Z)-icosatri-8,11,14-enoate(Z,Z,Z)-icosatri-8,11,14-enoic acid20:3, N-6,9,12 all-cis8,11,14-all-cis-Eicosatrienoate8,11,14-all-cis-Eicosatrienoic acid8,11,14-Eicosatrienoate8,11,14-Eicosatrienoic acid8,11,14-Icosatrienoate8,11,14-Icosatrienoic acid8c,11c,14c-Eicosatrienoate8c,11c,14c-Eicosatrienoic acid8c,11c,14c-Eicosatriensaeure8Z,11Z,14Z-eicosatrienoate8Z,11Z,14Z-eicosatrienoic acidall-cis-8,11,14-Eicosatrienoateall-cis-8,11,14-Eicosatrienoic acidall-cis-8,11,14-Icosatrienoateall-cis-8,11,14-Icosatrienoic acidall-cis-Eicosa-8,11,14-trienoateall-cis-Eicosa-8,11,14-trienoic acidall-cis-Eicosa-8,11,14-triensaeureBishomo-gamma-linolenateBishomo-gamma-linolenic acidC20:3, N-6,9,12 all-ciscis-8,11,14-Eicosatrienoatecis-8,11,14-Eicosatrienoic acidcis-8,cis-11,cis-14-Eicosatrienoatecis-8,cis-11,cis-14-Eicosatrienoic acidcis,cis,cis-8,11,14-Eicosatrienoatecis,cis,cis-8,11,14-Eicosatrienoic acidDGLADihomo-g-linolenateDihomo-g-linolenic acidDihomo-gamma-linolenateDihomo-gamma-linolenic acidDihomo-γ-linolenateDihomo-γ-linolenic acidEicosa-8Z,11Z,14Z-trienoateEicosa-8Z,11Z,14Z-trienoic acidEicosatrienoateEicosatrienoic acidg-Homolinolenateg-Homolinolenic acidgamma-Homolinolenategamma-Homolinolenic acidHomo-g-linolenateHomo-g-linolenic acidHomo-g-linolensaeureHomo-gamma-linolenateHomo-gamma-linolenic acidHomo-gamma-linolensaeureHomo-γ-linolenateHomo-γ-linolenic acidHomo-γ-linolensaeureγ-homolinolenateγ-homolinolenic acidC20H34O2306.4828306.255880332icosa-8,11,14-trienoic aciddihomo-gamma-linolenic acid1783-84-2CCCCCC=CCC=CCC=CCCCCCCC(O)=OInChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)HOBAELRKJCKHQD-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.Long-chain fatty acidsOrganic compoundsLipids and lipid-like moleculesFatty AcylsFatty acids and conjugatesAliphatic acyclic compoundsCarbonyl compoundsCarboxylic acidsHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesStraight chain fatty acidsUnsaturated fatty acidsAliphatic acyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeHydrocarbon derivativeLong-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundStraight chain fatty acidUnsaturated fatty acidSolidlogp7.24logs-6.60solubility7.71e-05 g/llogp6.95pka_strongest_acidic4.89iupacicosa-8,11,14-trienoic acidaverage_mass306.4828mono_mass306.255880332smilesCCCCCC=CCC=CCC=CCCCCCCC(O)=OformulaC20H34O2inchiInChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)inchikeyHOBAELRKJCKHQD-UHFFFAOYSA-Npolar_surface_area37.3refractivity98.84polarizability38.63rotatable_bond_count15acceptor_count2donor_count1physiological_charge-1formal_charge0Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592Specdb::CMs115071Specdb::CMs129319Specdb::CMs831029Specdb::CMs831030Specdb::MsMs3410327Specdb::MsMs3410328Specdb::MsMs3410329Specdb::MsMs3411128Specdb::MsMs3411129Specdb::MsMs3411130HMDB02925LAX#<Reference:0x00005556740e2bd8>#<Reference:0x00005556740e2a20>#<Reference:0x00005556740e2868>#<Reference:0x00005556740e2660>#<Reference:0x00005556740e2480>#<Reference:0x00005556740e22c8>Milk (Cow)Type 2specific2512.37452577.6312447.118uMAcyl-coenzyme A thioesterase 1Q86TX2ACOT1Acyl-coenzyme A thioesterase 2, mitochondrialP49753ACOT2Acyl-coenzyme A thioesterase 4Q8N9L9ACOT4Acyl-coenzyme A thioesterase 8O14734ACOT8Bile acid-CoA:amino acid N-acyltransferaseQ14032BAATCytosolic acyl coenzyme A thioester hydrolaseO00154ACOT7