1.0 2016-10-03 18:40:48 UTC 2020-06-04 20:34:00 UTC BMDB0003073 BMDB03073 Gamma-Linolenic acid Gamma-Linolenic acid, also known as 18:3 (N-6) or GLA, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Gamma-Linolenic acid exists in all living organisms, ranging from bacteria to humans. Gamma-Linolenic acid participates in a number of enzymatic reactions, within cattle. In particular, Gamma-Linolenic acid can be biosynthesized from linoleic acid; which is mediated by the enzyme fatty acid desaturase 2. In addition, Gamma-Linolenic acid can be converted into 8,11,14-eicosatrienoic acid; which is mediated by the enzyme elongation OF very long chain fatty acids protein 5. In cattle, Gamma-linolenic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. Gamma-Linolenic acid has been found to be associated with several diseases known as colorectal cancer and lung cancer; also gamma-linolenic acid has been linked to the inborn metabolic disorders including isovaleric acidemia. (6,9,12)-Linolenic acid (6Z,9Z,12Z)-Octadecatrienoic acid (Z,Z,Z)-6,9,12-Octadecatrienoic acid 18:3 (N-6) 6,9,12-Octadecatrienoic acid 6-cis,9-cis,12-cis-Octadecatrienoic acid all-cis-6,9,12-Octadecatrienoic acid C18:3 (N-6) C18:3, N-6,9,12 all-cis cis-Delta(6,9,12)-Octadecatrienoic acid gamma-Linolensaeure Gamoleic acid Gamolenic acid GLA Octadeca-6,9,12-triensaeure (6,9,12)-Linolenate (6Z,9Z,12Z)-Octadecatrienoate (Z,Z,Z)-6,9,12-Octadecatrienoate 6,9,12-Octadecatrienoate 6-cis,9-cis,12-cis-Octadecatrienoate all-cis-6,9,12-Octadecatrienoate cis-delta(6,9,12)-Octadecatrienoate cis-Δ(6,9,12)-octadecatrienoate cis-Δ(6,9,12)-octadecatrienoic acid g-Linolensaeure Γ-linolensaeure Gamoleate Gamolenate g-Linolenate g-Linolenic acid gamma-Linolenate Γ-linolenate Γ-linolenic acid 6(Z),9(Z),12(Z)-Octadecatrienoate 6(Z),9(Z),12(Z)-Octadecatrienoic acid 6,9,12-all-cis-Octadecatrienoate 6,9,12-all-cis-Octadecatrienoic acid 6Z,9Z,12Z-Octadecatrienoate 6Z,9Z,12Z-Octadecatrienoic acid gamma-Llnolenic acid Ligla Acid, gamma-linolenic Acid, gamolenic gamma Linolenic acid FA(18:3(6Z,9Z,12Z)) FA(18:3n6) Linolenate gamma-Linolenic acid (6Z,9Z,12Z)-6,9,12-Octadecatrienoic acid (Z,Z,Z)-6,9,12-Octatrienoic acid cis,cis,cis-6,9,12-Octadecatrienoic acid cis-6,cis-9,cis-12-Octadecatrienoic acid C18H30O2 278.4296 278.224580204 (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid gamma linolenic acid 506-26-3 CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- VZCCETWTMQHEPK-QNEBEIHSSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Lineolic acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Aliphatic acyclic compounds Polyunsaturated fatty acids Unsaturated fatty acids Unsaturated fatty acids linolenic acid omega-6 fatty acid Liquid logp 6.59 ALOGPS logs -6.04 ALOGPS logp 6.06 ChemAxon pka_strongest_acidic 4.92 ChemAxon iupac (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid ChemAxon average_mass 278.4296 ChemAxon mono_mass 278.224580204 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O ChemAxon formula C18H30O2 ChemAxon inchi InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- ChemAxon inchikey VZCCETWTMQHEPK-QNEBEIHSSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 89.64 ChemAxon polarizability 33.8 ChemAxon rotatable_bond_count 13 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::CMs 1862 Specdb::CMs 25150 Specdb::CMs 30905 Specdb::CMs 31440 Specdb::CMs 38520 Specdb::CMs 130350 Specdb::CMs 138084 Specdb::EiMs 1876 Specdb::NmrOneD 332658 Specdb::NmrOneD 332659 Specdb::NmrOneD 332660 Specdb::NmrOneD 332661 Specdb::NmrOneD 332662 Specdb::NmrOneD 332663 Specdb::NmrOneD 332664 Specdb::NmrOneD 332665 Specdb::NmrOneD 332666 Specdb::NmrOneD 332667 Specdb::NmrOneD 332668 Specdb::NmrOneD 332669 Specdb::NmrOneD 332670 Specdb::NmrOneD 332671 Specdb::NmrOneD 332672 Specdb::NmrOneD 332673 Specdb::NmrOneD 332674 Specdb::NmrOneD 332675 Specdb::NmrOneD 332676 Specdb::NmrOneD 332677 Specdb::MsMs 107205 Specdb::MsMs 107206 Specdb::MsMs 107207 Specdb::MsMs 174114 Specdb::MsMs 174115 Specdb::MsMs 174116 Specdb::MsMs 285956 Specdb::MsMs 285957 Specdb::MsMs 285958 Specdb::MsMs 285959 Specdb::MsMs 373980 Specdb::MsMs 373981 Specdb::MsMs 373982 Specdb::MsMs 373983 Specdb::MsMs 373984 Specdb::MsMs 439127 Specdb::MsMs 440460 Specdb::MsMs 440461 Specdb::MsMs 440462 Specdb::MsMs 1470916 Specdb::MsMs 1470917 Specdb::MsMs 1470918 Specdb::MsMs 2227000 Specdb::MsMs 2227217 Specdb::MsMs 2227698 Adipose Tissue 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 Epidermis 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 Milk Whole milk Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Milk 2837.338 +/- 682.398 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Milk 2693.675 +/- 574.651 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Oocyte Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries. McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70. 10793638 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 Platelet 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 C06426 DB13854 4444436 FDB002943 5280933 28661 CPD-8117 C00001226 48234 Gamma-Linolenic_acid 386 Gema H; Kavadia A; Dimou D; Tsagou V; Komaitis M; Aggelis G Production of gamma-linolenic acid by Cunninghamella echinulata cultivated on glucose and orange peel. Applied microbiology and biotechnology (2002), 58(3), 303-7. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. 1779072 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 BMDBP00001 Acyl-CoA 6-desaturase A4FV48 FADS2 Enzyme BMDBP02859 Elongation of very long chain fatty acids protein 5 Q2KJD9 ELOVL5 Enzyme