1.0 2011-09-21 00:24:24 UTC 2019-11-26 03:21:07 UTC FDB023082 8,11,14-Eicosatrienoic acid 8,11,14-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 acid 20:3, N-6,9,12 all-cis 8,11,14-all-cis-Eicosatrienoate 8,11,14-all-cis-Eicosatrienoic acid 8,11,14-Eicosatrienoate 8,11,14-Eicosatrienoic acid 8,11,14-Icosatrienoate 8,11,14-Icosatrienoic acid 8c,11c,14c-Eicosatrienoate 8c,11c,14c-Eicosatrienoic acid 8c,11c,14c-Eicosatriensaeure 8Z,11Z,14Z-eicosatrienoate 8Z,11Z,14Z-eicosatrienoic acid all-cis-8,11,14-Eicosatrienoate all-cis-8,11,14-Eicosatrienoic acid all-cis-8,11,14-Icosatrienoate all-cis-8,11,14-Icosatrienoic acid all-cis-Eicosa-8,11,14-trienoate all-cis-Eicosa-8,11,14-trienoic acid all-cis-Eicosa-8,11,14-triensaeure Bishomo-gamma-linolenate Bishomo-gamma-linolenic acid C20:3, N-6,9,12 all-cis cis-8,11,14-Eicosatrienoate cis-8,11,14-Eicosatrienoic acid cis-8,cis-11,cis-14-Eicosatrienoate cis-8,cis-11,cis-14-Eicosatrienoic acid cis,cis,cis-8,11,14-Eicosatrienoate cis,cis,cis-8,11,14-Eicosatrienoic acid DGLA Dihomo-g-linolenate Dihomo-g-linolenic acid Dihomo-gamma-linolenate Dihomo-gamma-linolenic acid Dihomo-γ-linolenate Dihomo-γ-linolenic acid Eicosa-8Z,11Z,14Z-trienoate Eicosa-8Z,11Z,14Z-trienoic acid Eicosatrienoate Eicosatrienoic acid g-Homolinolenate g-Homolinolenic acid gamma-Homolinolenate gamma-Homolinolenic acid Homo-g-linolenate Homo-g-linolenic acid Homo-g-linolensaeure Homo-gamma-linolenate Homo-gamma-linolenic acid Homo-gamma-linolensaeure Homo-γ-linolenate Homo-γ-linolenic acid Homo-γ-linolensaeure γ-homolinolenate γ-homolinolenic acid C20H34O2 306.4828 306.255880332 icosa-8,11,14-trienoic acid dihomo-gamma-linolenic acid 1783-84-2 CCCCCC=CCC=CCC=CCCCCCCC(O)=O InChI=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 acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Solid logp 7.24 ALOGPS logs -6.60 ALOGPS solubility 7.71e-05 g/l ALOGPS logp 6.95 ChemAxon pka_strongest_acidic 4.89 ChemAxon iupac icosa-8,11,14-trienoic acid ChemAxon average_mass 306.4828 ChemAxon mono_mass 306.255880332 ChemAxon smiles CCCCCC=CCC=CCC=CCCCCCCC(O)=O ChemAxon formula C20H34O2 ChemAxon inchi InChI=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) ChemAxon inchikey HOBAELRKJCKHQD-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 98.84 ChemAxon polarizability 38.63 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Alpha Linolenic Acid and Linoleic Acid Metabolism SMP00018 map00592 Specdb::CMs 115071 Specdb::CMs 129319 Specdb::CMs 831029 Specdb::CMs 831030 Specdb::MsMs 3410327 Specdb::MsMs 3410328 Specdb::MsMs 3410329 Specdb::MsMs 3411128 Specdb::MsMs 3411129 Specdb::MsMs 3411130 HMDB02925 LAX #<Reference:0x000055ce31c70538> #<Reference:0x000055ce31c702b8> #<Reference:0x000055ce31c70060> #<Reference:0x000055ce31c6fe58> #<Reference:0x000055ce31c6fca0> #<Reference:0x000055ce31c6fae8> Milk (Cow) Type 2 specific 2512.3745 2577.631 2447.118 uM Acyl-coenzyme A thioesterase 1 Q86TX2 ACOT1 Acyl-coenzyme A thioesterase 2, mitochondrial P49753 ACOT2 Acyl-coenzyme A thioesterase 4 Q8N9L9 ACOT4 Acyl-coenzyme A thioesterase 8 O14734 ACOT8 Bile acid-CoA:amino acid N-acyltransferase Q14032 BAAT Cytosolic acyl coenzyme A thioester hydrolase O00154 ACOT7