1.0 2020-03-31 16:40:29 UTC 2020-06-04 21:13:30 UTC BMDB0109633 Dihomo-gamma-linolenic acid (8Z,11Z,14Z)-Icosatrienoic acid (Z,Z,Z)-8,11,14-Eicosatrienoic acid (Z,Z,Z)-8,11,14-Icosatrienoate (Z,Z,Z)-8,11,14-Icosatrienoic acid 20:3, N-6,9,12 all-cis 8,11,14-Eicosatrienoic acid 8C,11C,14C-Eicosatrienoic acid 8C,11C,14C-Eicosatriensaeure 8Z,11Z,14Z-Eicosatrienoic acid all-cis-8,11,14-Eicosatrienoic acid all-cis-8,11,14-Icosatrienoic acid all-cis-Eicosa-8,11,14-trienoic acid all-cis-Eicosa-8,11,14-triensaeure C20:3, N-6,9,12 all-cis cis,cis,cis-8,11,14-Eicosatrienoic acid DGLA Eicosa-8Z,11Z,14Z-trienoic acid gamma-Homolinolenic acid Homo-gamma-linolenic acid Homo-gamma-linolensaeure (Z,Z,Z)-8,11,14-Eicosatrienoate 8,11,14-Eicosatrienoate 8,11,14-Icosatrienoate (8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid (8Z,11Z,14Z)-Icosatrienoate 8C,11C,14C-Eicosatrienoate 8Z,11Z,14Z-Eicosatrienoate all-cis-8,11,14-Eicosatrienoate all-cis-8,11,14-Icosatrienoate all-cis-Eicosa-8,11,14-trienoate cis,cis,cis-8,11,14-Eicosatrienoate Eicosa-8Z,11Z,14Z-trienoate g-Homolinolenate g-Homolinolenic acid gamma-Homolinolenate Γ-homolinolenate Γ-homolinolenic acid Homo-g-linolenate Homo-g-linolenic acid Homo-gamma-linolenate Homo-γ-linolenate Homo-γ-linolenic acid Homo-g-linolensaeure Homo-γ-linolensaeure 8,11,14-Icosatrienoic acid (8Z,11Z,14Z)-Icosa-8,11,14-trienoate Dihomo-g-linolenate Dihomo-g-linolenic acid Dihomo-gamma-linolenate Dihomo-γ-linolenate Dihomo-γ-linolenic acid Dihomogammalinolenic acid Dihomo gamma linolenic acid Homo-gamma linolenic acid Homo gamma linolenic acid Linolenic acid, homo-gamma 8,11,14 Eicosatrienoic acid (Z,Z,Z)-Icosatri-8,11,14-enoate (Z,Z,Z)-Icosatri-8,11,14-enoic acid 8,11,14-all-cis-Eicosatrienoate 8,11,14-all-cis-Eicosatrienoic acid Bishomo-gamma-linolenate Bishomo-gamma-linolenic acid 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 Eicosatrienoate Eicosatrienoic acid Acid, dihomo-gamma-linolenic DHLA Acid, dihomogammalinolenic Acid, homo-gamma linolenic Dihomolinolenate Dihomolinolenic acid FA(20:3(8Z,11Z,14Z)) Dihomo-linolenate Dihomo-linolenic acid FA(20:3n6) dihomo-gamma-Linolenic acid C20H34O2 306.4828 306.255880332 (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid dihomo-gamma-linolenic acid 1783-84-2 CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(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)/b7-6-,10-9-,13-12- HOBAELRKJCKHQD-QNEBEIHSSA-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. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Long-chain fatty acids 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 Aliphatic acyclic compounds Polyunsaturated fatty acids Unsaturated fatty acids icosatrienoic acid long-chain fatty acid logp 7.24 ALOGPS logs -6.60 ALOGPS logp 6.95 ChemAxon pka_strongest_acidic 4.89 ChemAxon iupac (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid ChemAxon average_mass 306.4828 ChemAxon mono_mass 306.255880332 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(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)/b7-6-,10-9-,13-12- ChemAxon inchikey HOBAELRKJCKHQD-QNEBEIHSSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 98.84 ChemAxon polarizability 39.01 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 2166 Specdb::MsMs 2167 Specdb::MsMs 2168 Specdb::MsMs 244887 Specdb::MsMs 244888 Specdb::MsMs 244889 Specdb::MsMs 264834 Specdb::MsMs 264835 Specdb::MsMs 264836 Specdb::MsMs 439965 Specdb::MsMs 450254 Specdb::MsMs 450255 Specdb::MsMs 2252387 Specdb::MsMs 2254079 Specdb::MsMs 2254437 Specdb::MsMs 2383193 Specdb::MsMs 2383194 Specdb::MsMs 2383195 Specdb::MsMs 2582435 Specdb::MsMs 2582436 Specdb::MsMs 2582437 Specdb::NmrTwoD 1849 Specdb::CMs 6033 Specdb::CMs 38498 Specdb::CMs 137218 Specdb::CMs 144952 Specdb::NmrOneD 1914 Specdb::NmrOneD 328052 Specdb::NmrOneD 328053 Specdb::NmrOneD 328054 Specdb::NmrOneD 328055 Specdb::NmrOneD 328056 Specdb::NmrOneD 328057 Specdb::NmrOneD 328058 Specdb::NmrOneD 328059 Specdb::NmrOneD 328060 Specdb::NmrOneD 328061 Specdb::NmrOneD 328062 Specdb::NmrOneD 328063 Specdb::NmrOneD 328064 Specdb::NmrOneD 328065 Specdb::NmrOneD 328066 Specdb::NmrOneD 328067 Specdb::NmrOneD 328068 Specdb::NmrOneD 328069 Specdb::NmrOneD 328070 Specdb::NmrOneD 328071 Adipose Tissue 1468.27 nmol/g of tissue Fatty acid of subcutaneous fat. Calf-finished Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 1174.62 nmol/g of tissue Fatty acid of subcutaneous fat. With growth promoting implants Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 1500.9 nmol/g of tissue Fatty acid of subcutaneous fat. Without growth promoting implants Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 1213.77 nmol/g of tissue Fatty acid of subcutaneous fat. Yearling-finished Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 193.52 nmol/g of tissue Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 339.73 nmol/g of tissue Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue 308.89 nmol/g of tissue Perirenal (PF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 1787.57 nmol/g of tissue Perirenal (PF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 866.97 nmol/g of tissue Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 1603.55 nmol/g of tissue Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 DB00154 4444199 5280581 C03242 53486 FDB023082 41475 Dihomo-γ-linolenic acid 259