1.0 2016-10-03 18:41:27 UTC 2020-06-04 21:03:00 UTC BMDB0060039 BMDB60039 11,14,17-Eicosatrienoic acid 11,14,17-Eicosatrienoic acid, also known as 20:3, N-3,6,9 all-cis or ETA, 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. 11,14,17-Eicosatrienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acid (11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid (Z,Z,Z)-11,14,17-Eicosatrienoic acid 11,14,17-Eicosatrienoic acid 11,14,17-Icosatrienoic acid 11C,14C,17C-Eicosatrienoic acid 11C,14C,17C-Eicosatriensaeure 20:3, N-3,6,9 all-cis all-cis-11,14,17-Eicosatrienoic acid all-cis-Eicosa-11,14,17-trienoic acid all-cis-Eicosa-11,14,17-triensaeure C20:3, N-3,6,9 all-cis cis,cis,cis-11,14,17-Eicosatrienoic acid Eicosa-11Z,14Z,17Z-trienoic acid Eicosatrienoic acid ETA ETE (11Z,14Z,17Z)-Eicosa-11,14,17-trienoate (11Z,14Z,17Z)-Icosa-11,14,17-trienoate (Z,Z,Z)-11,14,17-Eicosatrienoate 11,14,17-Eicosatrienoate 11,14,17-Icosatrienoate 11C,14C,17C-Eicosatrienoate all-cis-11,14,17-Eicosatrienoate all-cis-Eicosa-11,14,17-trienoate cis,cis,cis-11,14,17-Eicosatrienoate Eicosa-11Z,14Z,17Z-trienoate Eicosatrienoate Dihomo-a-linolenate Dihomo-a-linolenic acid Dihomo-alpha-linolenate Dihomo-α-linolenate Dihomo-α-linolenic acid Dihomolinolenate 11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomer Bishomo-a-linolenate Bishomo-a-linolenic acid Bishomo-alpha-linolenate Bishomo-α-linolenate Bishomo-α-linolenic acid Bishomo-alpha-linolenic acid Dihomo-linolenate Dihomo-linolenic acid Dihomolinolenic acid FA(20:3(11Z,14Z,17Z)) FA(20:3n3) Homo-alpha-linolenic acid Homo-α-linolenic acid Dihomo-alpha-linolenic acid C20H34O2 306.4828 306.255880332 (11Z,14Z,17Z)-icosa-11,14,17-trienoic acid eicosatrienoic acid 17046-59-2 CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(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/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9- AHANXAKGNAKFSK-PDBXOOCHSA-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 omega-3 fatty acid logp 7.24 ALOGPS logs -6.60 ALOGPS logp 6.95 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac (11Z,14Z,17Z)-icosa-11,14,17-trienoic acid ChemAxon average_mass 306.4828 ChemAxon mono_mass 306.255880332 ChemAxon smiles CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(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/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9- ChemAxon inchikey AHANXAKGNAKFSK-PDBXOOCHSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 98.84 ChemAxon polarizability 38.73 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 82533 Specdb::MsMs 82534 Specdb::MsMs 82535 Specdb::MsMs 143922 Specdb::MsMs 143923 Specdb::MsMs 143924 Specdb::MsMs 438674 Specdb::MsMs 3224362 Specdb::MsMs 3224363 Specdb::MsMs 3224364 Specdb::MsMs 3224365 Specdb::MsMs 3224366 Specdb::MsMs 3224367 Specdb::CMs 36684 Specdb::CMs 48025 Specdb::CMs 157333 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 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 64.51 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 53.64 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 926.68 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 595.86 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 801.77 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 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 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Milk 1109.360 +/- 456.795 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 946.219 +/- 326.282 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 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 This is a duplicate concentration of concentration_id 8153, unpexported by An Chi on Aug 20, 2018 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 Muscle Samples have been collected from Heifer cows. Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub 2013 Jun 5. 23871026 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 FDB006293 4471954 5312529 C16522 53460 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