1.0 2016-09-30 22:18:51 UTC 2020-06-04 22:46:52 UTC BMDB0000042 BMDB00042 Acetic acid Acetic acid, also known as glacial acetate or vinegar, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Acetic acid is a drug which is used to treat infections in the ear canal. Acetic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetic acid exists in all living species, ranging from bacteria to humans. Acetic acid has been found to be associated with several diseases known as colorectal cancer, gout, and perillyl alcohol administration for cancer treatment; also acetic acid has been linked to several inborn metabolic disorders including celiac disease and phenylketonuria. Acide acetique AcOH CH3-COOH CH3CO2H e 260 e-260 e260 Essigsaeure Ethanoic acid Ethoic acid Ethylic acid HOAc INS no. 260 MeCO2h MeCOOH Methanecarboxylic acid Glacial acetic acid Acetasol Ethanoate Ethoate Ethylate Methanecarboxylate Glacial acetate Acetate Kyselina octova Vinegar Vinegar acid Acid, acetic Acetic acid glacial Acid glacial, acetic Acid, glacial acetic Acetic acid, glacial Glacial, acetic acid C2H4O2 60.052 60.021129372 acetic acid acetic acid 64-19-7 CC(O)=O InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) QTBSBXVTEAMEQO-UHFFFAOYSA-N belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acids Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Aliphatic acyclic compounds Saturated fatty acids Straight chain fatty acids Straight chain fatty acids monocarboxylic acid Liquid melting_point 16.6 °C water_solubility 1000.0 mg/mL logp -0.17 HANSCH,C ET AL. (1995) logp -0.12 ALOGPS logs 0.73 ALOGPS logp -0.22 ChemAxon pka_strongest_acidic 4.54 ChemAxon iupac acetic acid ChemAxon average_mass 60.052 ChemAxon mono_mass 60.021129372 ChemAxon smiles CC(O)=O ChemAxon formula C2H4O2 ChemAxon inchi InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) ChemAxon inchikey QTBSBXVTEAMEQO-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 12.64 ChemAxon polarizability 5.34 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Amino Sugar Metabolism SMP0087175 Aspartate Metabolism SMP0087165 Ethanol Degradation SMP0087192 Fatty Acid Biosynthesis SMP0087257 Pyruvate Metabolism SMP0087231 Specdb::CMs 3237 Specdb::CMs 29450 Specdb::CMs 37262 Specdb::CMs 99523 Specdb::CMs 134868 Specdb::CMs 142602 Specdb::CMs 1047402 Specdb::EiMs 1279 Specdb::NmrTwoD 939 Specdb::NmrTwoD 1106 Specdb::MsIr 118 Specdb::MsIr 119 Specdb::MsIr 120 Specdb::MsMs 69 Specdb::MsMs 70 Specdb::MsMs 71 Specdb::MsMs 2635 Specdb::MsMs 2636 Specdb::MsMs 2637 Specdb::MsMs 2638 Specdb::MsMs 2639 Specdb::MsMs 2640 Specdb::MsMs 179742 Specdb::MsMs 179743 Specdb::MsMs 179744 Specdb::MsMs 182076 Specdb::MsMs 182077 Specdb::MsMs 182078 Specdb::MsMs 437112 Specdb::MsMs 437113 Specdb::MsMs 437114 Specdb::MsMs 437115 Specdb::MsMs 437116 Specdb::MsMs 2268979 Specdb::MsMs 2268980 Specdb::MsMs 2268981 Specdb::MsMs 3072966 Specdb::MsMs 3072967 Specdb::NmrOneD 1048 Specdb::NmrOneD 1126 Specdb::NmrOneD 2560 Specdb::NmrOneD 3258 Specdb::NmrOneD 4746 Specdb::NmrOneD 5432 Specdb::NmrOneD 5433 Specdb::NmrOneD 5434 Specdb::NmrOneD 5435 Specdb::NmrOneD 5436 Specdb::NmrOneD 5437 Specdb::NmrOneD 5438 Specdb::NmrOneD 5439 Specdb::NmrOneD 5440 Specdb::NmrOneD 5441 Specdb::NmrOneD 5442 Specdb::NmrOneD 5443 Specdb::NmrOneD 5444 Specdb::NmrOneD 5445 Specdb::NmrOneD 5446 Specdb::NmrOneD 5447 Specdb::NmrOneD 5448 Specdb::NmrOneD 5449 Specdb::NmrOneD 5450 Specdb::NmrOneD 5451 Blood Detected by NMR in multiparous-early lactation Holstein cows. Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17. 24440255 Blood Jiyuan Li, Everestus C. Akanno, Tiago Valente, Mohammed Abo-Ismail, Brian Karisa, Zhiquan Wang, Graham S. Plastow. Genomic heritability and genome-wide association studies of plasma metabolites in crossbred beef cattle. (in preparation) Blood 403 +/- 199 uM By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Blood 1500-2400 uM By GC-MS Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999. 21524548 Blood 920-1040 uM Boehringer Mannheim F-kit for acetate Sato H, Matsumoto M, Hanasaka S: Relations between plasma acetate, 3-hydroxybutyrate, FFA, glucose levels and energy nutrition in lactating dairy cows. J Vet Med Sci. 1999 May;61(5):447-51. doi: 10.1292/jvms.61.447. 10379932 Blood Detected by NMR De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014. 25372282 Colostrum Detected by NMR Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15. 25637742 Kidney 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 Liver 201 +/- 91 nmol/g of tissue By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Longissimus Thoracis Muscle 188 +/- 31 nmol/g of tissue By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Milk 135.52 +/- 1.49 uM 3.5% Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990 Milk 108 - 701 uM Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. 20338431 Milk 38 +/- 1 uM Commercial skim milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 13 - 37 uM Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. 22098372 Milk 13 - 37 uM Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. 23497994 Milk 37 +/- 1 uM Commercial 1% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 46 +/- 1 uM Commercial 2% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 28 +/- 2 uM 1% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 30 +/- 2 uM 2% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 31 +/- 2 uM 3.25% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 33 +/- 3 uM Skim milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 43 +/- 1 uM Commercial 3.25% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 14 - 35 uM Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. 22098372 Milk 97.08 +/- 3.88 uM Whole milk Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990 Milk 41.47 +/- 10.17 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk Milk samples from 20 healthy Holstein Friesian dairy cows Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. 23738862 Milk Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436) Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. 23182357 Milk 407 Milk samples from Swedish Red cows Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. 25087032 Milk 47.88 +/- 12.36 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 6.8 (2.6 - 7.7) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 5.7 (2.8 - 7.6) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 9.6 (2.6 - 23) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 71.81 +/- 41.67 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 95 (11 - 199) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Muscle Detected by NMR Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15. 25637742 Muscle 111.28 +/- 14.21 uM Detected by NMR in Australian commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 5170 +/- 1070 nmol/g of tissue Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days. S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404 doi: 10.1007/s11306-010-0206-y Muscle 7290 +/- 1470 nmol/g of tissue Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days. S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404 doi: 10.1007/s11306-010-0206-y Muscle 3190 +/- 750 nmol/g of tissue Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days. S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404 doi: 10.1007/s11306-010-0206-y Muscle 4440 +/- 950 nmol/g of tissue Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days. S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404 doi: 10.1007/s11306-010-0206-y Muscle 252.43 +/- 27.85 uM Detected by NMR in US commercial beef sirloin Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 261.32 +/- 30.52 uM Detected by NMR in Korean commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 274.35 +/- 13.29 uM Detected by NMR in New Zealand commercial beef sirloin. Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 97-291 nmol/g of tissue By NMR Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t. 20831251 Muscle 97-133 nmol/g of tissue By NMR Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8. 28465593 Ruminal Fluid 41000-81000 uM By NMR Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid 48146-62076 uM By NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Ruminal Fluid 43800 uM By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 41400 uM By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 56500 uM By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 47600 uM By NMR. Primiparous Holstein cows, no barley grains in diet. Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid Detected by NMR in mid-lactating primiparous Holstein cows. Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr 4. 24617926 Ruminal Fluid 37264 +/- 7582 uM By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in male Holstein cows. Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, Søren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134 doi: 10.1016/j.livsci.2008.05.001 Ruminal Fluid 60087.08 +/- 5781.35 uM Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 56300 uM By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 54600 uM By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 64270 uM By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 60100 uM By NMR. No barley grains in diet (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 56350 +/- 7280 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 54620 +/- 7940 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 64280 +/- 6040 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 60100 +/- 5800 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Semen Identified in bull spermatozoa by GC-MS Menezes EB, Velho ALC, Santos F, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Uncovering sperm metabolome to discover biomarkers for bull fertility. BMC Genomics. 2019 Sep 18;20(1):714. doi: 10.1186/s12864-019-6074-6. 31533629 Semen Identified in bull spermatozoa by GC-MS Menezes EB, Velho ALC, Santos F, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Uncovering sperm metabolome to discover biomarkers for bull fertility. BMC Genomics. 2019 Sep 18;20(1):714. doi: 10.1186/s12864-019-6074-6. 31533629 Semimembranosus Muscle 219 +/- 52 nmol/g of tissue By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Testis 88 +/- 19 nmol/g of tissue By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Urine Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein. Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17. 22059599 DB03166 C00033 171 176 FDB019725 15366 C00001176 ACET Acetic_acid 33590 3206 Law, David John. Process for the preparation of carboxylic acids and/or derivatives thereof. PCT Int. Appl. (2007), 14pp. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. 20338431 Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. 22098372 Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. 23182357 Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. 25087032 Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. 23497994 Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. 23738862 O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00151 Acylphosphatase-1 P41500 ACYP1 Enzyme BMDBP00367 Acyl-CoA synthetase short-chain family member 3, mitochondrial A7MB45 ACSS3 Enzyme BMDBP00368 Fatty acid synthase Q71SP7 FASN Enzyme BMDBP00529 Acetylcholinesterase P23795 ACHE Enzyme BMDBP00562 Aspartoacylase P46446 ASPA Enzyme BMDBP00938 N-acetylglucosamine-6-phosphate deacetylase A7MBC0 AMDHD2 Enzyme BMDBP00943 Platelet-activating factor acetylhydrolase 2, cytoplasmic P79106 PAFAH2 Enzyme BMDBP00944 Platelet-activating factor acetylhydrolase Q28017 PLA2G7 Enzyme BMDBP00945 Platelet-activating factor acetylhydrolase IB subunit gamma Q29460 PAFAH1B3 Enzyme BMDBP00946 Serum paraoxonase/arylesterase 2 Q58DS7 PON2 Enzyme BMDBP00947 Platelet-activating factor acetylhydrolase IB subunit beta P68401 PAFAH1B2 Enzyme BMDBP00948 N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase A6QQ24 PIGL Enzyme BMDBP02881 ACSS2 protein A7YWF1 ACSS2 Enzyme BMDBP02919 Acyl-CoA thioesterase 12 E1BNW7 ACOT12 Enzyme BMDBP02978 Acetyl-coenzyme A synthetase Q9BEA3 AceCS2 Enzyme