1.0 2018-06-29 22:18:42 UTC 2020-06-04 21:25:57 UTC BMDB0062205 BMDB62205 Gadoleic acid 9Z-Eicosenoic acid, also known as cis-gadoleate or 9C-eicosensaeure, 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. 9Z-Eicosenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (Z)-Eicos-9-enoic acid 9C-Eicosensaeure C20:1C cis-9-Eicosenoic acid cis-Delta(9)-Eicosenoic acid Eicos-9C-enoic acid Eicos-9C-ensaeure (Z)-Eicos-9-enoate cis-9-Eicosenoate cis-delta(9)-Eicosenoate cis-Δ(9)-eicosenoate cis-Δ(9)-eicosenoic acid Eicos-9C-enoate 9Z-Eicosenoate Gadoleate Gadoleic acid FA(20:1(9Z)) cis-Gadoleate C20H38O2 310.522 310.287180464 (9Z)-icos-9-enoic acid gadoleic acid 29204-02-2 [H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11- LQJBNNIYVWPHFW-QXMHVHEDSA-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 Unsaturated fatty acids icosenoic acid logp 8.41 ALOGPS logs -6.80 ALOGPS logp 7.67 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9Z)-icos-9-enoic acid ChemAxon average_mass 310.522 ChemAxon mono_mass 310.287180464 ChemAxon smiles [H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O ChemAxon formula C20H38O2 ChemAxon inchi InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11- ChemAxon inchikey LQJBNNIYVWPHFW-QXMHVHEDSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 96.6 ChemAxon polarizability 41.32 ChemAxon rotatable_bond_count 17 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 34769 Specdb::CMs 48917 Specdb::CMs 131728 Specdb::CMs 139462 Specdb::MsMs 70611 Specdb::MsMs 70612 Specdb::MsMs 70613 Specdb::MsMs 129141 Specdb::MsMs 129142 Specdb::MsMs 129143 Specdb::MsMs 2375363 Specdb::MsMs 2375364 Specdb::MsMs 2375365 Specdb::MsMs 2559498 Specdb::MsMs 2559499 Specdb::MsMs 2559500 Adipose Tissue 3692.94 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 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 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 Adipose Tissue 2608.51 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 1449.17 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 1777.65 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 598.99 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 169.78 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 158.83 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 1829.24 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 2646.48 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 3707.98 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. Milk 96.612 uM Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 96.612 uM Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 96.612 uM Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1255.95 uM Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en 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 FDB003771 4445894 5282767 C00053190 32419 Gadoleic acid Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. 29570652 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en