1.0 2016-09-30 23:23:02 UTC 2020-06-04 21:15:45 UTC BMDB0006528 BMDB06528 Clupanodonic acid Docosapentaenoic acid (22N-3), also known as DPA or docosapentaenoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosapentaenoic acid (22N-3) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Docosapentaenoic acid (22N-3) participates in a number of enzymatic reactions, within cattle. In particular, Docosapentaenoic acid (22N-3) can be biosynthesized from eicosapentaenoic acid through its interaction with the enzyme elongation OF very long chain fatty acids protein 5. In addition, Docosapentaenoic acid (22N-3) can be converted into tetracosapentaenoic acid (24:5N-3); which is catalyzed by the enzyme elongation OF very long chain fatty acids protein 4. In cattle, docosapentaenoic acid (22N-3) is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. Docosapentaenoic acid (22N-3) has been found to be associated with the diseases known as colorectal cancer; also docosapentaenoic acid (22n-3) has been linked to the inborn metabolic disorders including isovaleric acidemia. (7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid (all Z)-7,10,13,16,19-Docosapentaenoic acid all-cis-7,10,13,16,19-Docosapentaenoic acid cis-7,10,13,16,19-Docosapentaenoic acid Clupanodonic acid Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid Docosapentaenoic acid DPA DPAn-3 7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid (7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoate (all Z)-7,10,13,16,19-Docosapentaenoate all-cis-7,10,13,16,19-Docosapentaenoate cis-7,10,13,16,19-Docosapentaenoate Clupanodonate Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoate Docosapentaenoate 7Z,10Z,13Z,16Z,19Z-Docosapentaenoate Docosapentaenoate (22N-3) 7,10,13,16,19-Docosapentaenoic acid, (all-Z)-isomer Docosapentaenoic acid (C22:5 N3) Osbond acid (all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acid 7,10,13,16,19-Docosapentaenoic acid Docosapentaenoic acid, (all Z)-isomer (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoate (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acid 7,10,13,16,19-Docosapentaenoate FA(22:5(7Z,10Z,13Z,16Z,19Z)) (7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-Docosapentaenoic acid (all-Z)-7,10,13,16,19-Docosapentaenoic acid FA(22:5n3) delta7,10,13,16,19-Docosapentaenoic acid omega3-Docosapentaenoic acid Δ7,10,13,16,19-Docosapentaenoic acid ω3-Docosapentaenoic acid C22H34O2 330.5042 330.255880332 (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid clupanodonic acid 24880-45-3 CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15- YUFFSWGQGVEMMI-JLNKQSITSA-N belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Very 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 Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Very long-chain fatty acid Aliphatic acyclic compounds Docosanoids Docosanoids Polyunsaturated fatty acids docosapentaenoic acid omega-3 fatty acid Solid logp 7.08 ALOGPS logs -6.45 ALOGPS logp 7.11 ChemAxon pka_strongest_acidic 4.96 ChemAxon iupac (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid ChemAxon average_mass 330.5042 ChemAxon mono_mass 330.255880332 ChemAxon smiles CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O ChemAxon formula C22H34O2 ChemAxon inchi InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15- ChemAxon inchikey YUFFSWGQGVEMMI-JLNKQSITSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 110.27 ChemAxon polarizability 40.1 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 Alpha Linolenic Acid and Linoleic Acid Metabolism SMP0087171 Specdb::CMs 9590 Specdb::CMs 39033 Specdb::CMs 158747 Specdb::MsMs 287158 Specdb::MsMs 287159 Specdb::MsMs 287160 Specdb::MsMs 325921 Specdb::MsMs 325922 Specdb::MsMs 325923 Specdb::MsMs 438641 Specdb::MsMs 439966 Specdb::MsMs 450256 Specdb::MsMs 2317094 Specdb::MsMs 2317095 Specdb::MsMs 2317096 Specdb::MsMs 2622302 Specdb::MsMs 2622303 Specdb::MsMs 2622304 Specdb::NmrOneD 299185 Specdb::NmrOneD 299186 Specdb::NmrOneD 299187 Specdb::NmrOneD 299188 Specdb::NmrOneD 299189 Specdb::NmrOneD 299190 Specdb::NmrOneD 299191 Specdb::NmrOneD 299192 Specdb::NmrOneD 299193 Specdb::NmrOneD 299194 Specdb::NmrOneD 299195 Specdb::NmrOneD 299196 Specdb::NmrOneD 299197 Specdb::NmrOneD 299198 Specdb::NmrOneD 299199 Specdb::NmrOneD 299200 Specdb::NmrOneD 299201 Specdb::NmrOneD 299202 Specdb::NmrOneD 299203 Specdb::NmrOneD 299204 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 478.54 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 431.0989 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 1145.76 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 1381.37 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 1607.91 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 1982.67 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 Milk 1028.732 +/- 423.595 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 877.448 +/- 302.568 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 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 FDB021831 C16513 C00052249 4593750 5497182 53488 CPD-13792 2218032 Docosapentaenoic acid 194 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 BMDBP02859 Elongation of very long chain fatty acids protein 5 Q2KJD9 ELOVL5 Enzyme