1.0 2016-09-30 23:15:08 UTC 2020-06-04 20:33:30 UTC BMDB0005060 BMDB05060 Eicosadienoic acid Eicosadienoic acid, also known as 11,14-eicosadienoate or delta11,14-20:2, 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. Eicosadienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Eicosadienoic acid has been found to be associated with the diseases known as colorectal cancer; also eicosadienoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia. (11Z,14Z)-Eicosa-11,14-dienoic acid (11Z,14Z)-Eicosadienoic acid (11Z,14Z)-Icosa-11,14-dienoic acid 11,14-Eicosadienoic acid 11,14-Icosadienoic acid (11Z,14Z)-Eicosa-11,14-dienoate (11Z,14Z)-Eicosadienoate (11Z,14Z)-Icosa-11,14-dienoate 11,14-Eicosadienoate 11,14-Icosadienoate Eicosadienoate 11, 14-Icosadienoate 11, 14-Icosadienoic acid 11,14-trans-Eicosadienoic acid delta11,14-20:2 Eicosa-11,14-dienoic acid Eicosa-11,14-dienoic acid, (Z,Z)-isomer N-6 Eicosadienoic acid Dihomolinoleate (11Z,14Z)-Icosadienoate (11Z,14Z)-11,14-Eicosadienate (11Z,14Z)-11,14-Eicosadienic acid (11Z,14Z)-11,14-Eicosadienoate (11Z,14Z)-11,14-Eicosadienoic acid 11,14-all-cis-Eicosadienoate 11,14-all-cis-Eicosadienoic acid 11-cis,14-cis-Eicosadienoate 11-cis,14-cis-Eicosadienoic acid Bishomolinoleate Bishomolinoleic acid Dihomo-linoleate (20:2n6) Dihomo-linoleic acid (20:2n6) FA(20:2(11Z,14Z)) Homo-gamma-linoleate Homo-gamma-linoleic acid Homo-γ-linoleate Homo-γ-linoleic acid all-cis-11,14-Eicosadienoate all-cis-11,14-Eicosadienoic acid cis,cis-Eicosa-11,14-dienoate cis,cis-Eicosa-11,14-dienoic acid cis,cis-delta11,14-Eicosadienoate cis,cis-delta11,14-Eicosadienoic acid cis,cis-Δ11,14-eicosadienoate cis,cis-Δ11,14-eicosadienoic acid cis-11,cis-14-Eicosadienoate cis-11,cis-14-Eicosadienoic acid delta11,14-Eicosadienoate delta11,14-Eicosadienoic acid Δ11,14-eicosadienoate Δ11,14-eicosadienoic acid FA(20:2n6) Eicosadienoic acid C20H36O2 308.4986 308.271530396 (11Z,14Z)-icosa-11,14-dienoic acid eicosadienoic acid 5598-38-9 CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9- XSXIVVZCUAHUJO-HZJYTTRNSA-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 icosadienoic acid Solid logp 6.251 logp 7.83 ALOGPS logs -6.75 ALOGPS logp 7.31 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac (11Z,14Z)-icosa-11,14-dienoic acid ChemAxon average_mass 308.4986 ChemAxon mono_mass 308.271530396 ChemAxon smiles CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O ChemAxon formula C20H36O2 ChemAxon inchi InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9- ChemAxon inchikey XSXIVVZCUAHUJO-HZJYTTRNSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 97.72 ChemAxon polarizability 39.94 ChemAxon rotatable_bond_count 16 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 22192 Specdb::CMs 38849 Specdb::CMs 132811 Specdb::CMs 140545 Specdb::MsMs 315265 Specdb::MsMs 315266 Specdb::MsMs 315267 Specdb::MsMs 361201 Specdb::MsMs 361202 Specdb::MsMs 361203 Specdb::MsMs 438682 Specdb::MsMs 1476277 Specdb::MsMs 1476278 Specdb::MsMs 1476279 Specdb::MsMs 1476280 Specdb::MsMs 1476281 Specdb::MsMs 1476282 Specdb::MsMs 1476283 Specdb::MsMs 1476308 Specdb::MsMs 1476309 Specdb::MsMs 1476310 Specdb::MsMs 1476311 Specdb::MsMs 1476312 Specdb::MsMs 1476313 Specdb::MsMs 1476314 Specdb::MsMs 1476315 Specdb::MsMs 1476316 Specdb::MsMs 1476317 Specdb::MsMs 1476318 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 Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk 2560.786 +/- 615.885 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 2431.126 +/- 518.640 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 4944228 C16525 73731 6439848 FDB012619 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 Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. 19038946 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