1.0 2016-09-30 22:34:54 UTC 2020-06-04 22:32:44 UTC BMDB0000687 BMDB00687 L-Leucine L-Leucine, also known as (S)-leucine or L-leucin, belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Leucine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Leucine exists in all living species, ranging from bacteria to humans. L-Leucine can be converted into L-leucine through its interaction with the enzyme large neutral amino acids transporter small subunit 1. In cattle, L-leucine is involved in the metabolic pathway called the leucine stimulation ON insulin signaling pathway. L-Leucine is a potentially toxic compound. (2S)-2-Amino-4-methylpentanoic acid (2S)-alpha-2-Amino-4-methylvaleric acid (2S)-alpha-Leucine (S)-(+)-Leucine (S)-Leucine 2-Amino-4-methylvaleric acid L L-Leucin L-Leuzin Leu LEUCINE (2S)-2-Amino-4-methylpentanoate (2S)-a-2-Amino-4-methylvalerate (2S)-a-2-Amino-4-methylvaleric acid (2S)-alpha-2-Amino-4-methylvalerate (2S)-Α-2-amino-4-methylvalerate (2S)-Α-2-amino-4-methylvaleric acid (2S)-a-Leucine (2S)-Α-leucine 2-Amino-4-methylvalerate (S)-2-Amino-4-methylpentanoate (S)-2-Amino-4-methylpentanoic acid (S)-2-Amino-4-methylvalerate (S)-2-Amino-4-methylvaleric acid 4-Methyl-L-norvaline L-(+)-Leucine L-a-Aminoisocaproate L-a-Aminoisocaproic acid L-alpha-Aminoisocaproate L-alpha-Aminoisocaproic acid Leucine, L-isomer L-Isomer leucine Leucine, L isomer C6H13NO2 131.1729 131.094628665 (2S)-2-amino-4-methylpentanoic acid L-leucine 61-90-5 CC(C)C[C@H](N)C(O)=O InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 ROHFNLRQFUQHCH-YFKPBYRVSA-N belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Leucine and derivatives Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Methyl-branched fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Branched fatty acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Leucine or derivatives Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds Common amino acids L-alpha-amino acid leucine proteinogenic amino acid pyruvate family amino acid Solid melting_point 268 - 288 °C water_solubility 21.5 mg/mL logp -1.52 HANSCH,C ET AL. (1995) logp -1.82 ALOGPS logs -0.27 ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 2.79 ChemAxon pka_strongest_basic 9.52 ChemAxon iupac (2S)-2-amino-4-methylpentanoic acid ChemAxon average_mass 131.1729 ChemAxon mono_mass 131.094628665 ChemAxon smiles CC(C)C[C@H](N)C(O)=O ChemAxon formula C6H13NO2 ChemAxon inchi InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 ChemAxon inchikey ROHFNLRQFUQHCH-YFKPBYRVSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 34.17 ChemAxon polarizability 14.16 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 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 Leucine Stimulation on Insulin Signaling SMP0108000 Protein Synthesis: Leucine SMP0119403 Valine, Leucine, and Isoleucine Degradation SMP0087234 Specdb::NmrTwoD 1423 Specdb::EiMs 1983 Specdb::MsIr 19 Specdb::MsIr 739 Specdb::MsIr 740 Specdb::MsIr 741 Specdb::CMs 604 Specdb::CMs 605 Specdb::CMs 606 Specdb::CMs 607 Specdb::CMs 608 Specdb::CMs 2748 Specdb::CMs 28003 Specdb::CMs 30023 Specdb::CMs 30207 Specdb::CMs 30312 Specdb::CMs 30313 Specdb::CMs 30594 Specdb::CMs 30726 Specdb::CMs 30769 Specdb::CMs 37697 Specdb::CMs 131297 Specdb::CMs 139031 Specdb::CMs 1072453 Specdb::CMs 1072455 Specdb::CMs 1072456 Specdb::MsMs 951 Specdb::MsMs 952 Specdb::MsMs 953 Specdb::MsMs 4393 Specdb::MsMs 4394 Specdb::MsMs 4395 Specdb::MsMs 4396 Specdb::MsMs 4397 Specdb::MsMs 4398 Specdb::MsMs 4399 Specdb::MsMs 4400 Specdb::MsMs 4401 Specdb::MsMs 4402 Specdb::MsMs 4403 Specdb::MsMs 4404 Specdb::MsMs 4405 Specdb::MsMs 4406 Specdb::MsMs 4407 Specdb::MsMs 4408 Specdb::MsMs 4409 Specdb::MsMs 4410 Specdb::MsMs 4416 Specdb::MsMs 4417 Specdb::MsMs 4418 Specdb::MsMs 178782 Specdb::NmrOneD 1251 Specdb::NmrOneD 1477 Specdb::NmrOneD 4877 Specdb::NmrOneD 144830 Specdb::NmrOneD 144831 Specdb::NmrOneD 144832 Specdb::NmrOneD 144833 Specdb::NmrOneD 144834 Specdb::NmrOneD 144835 Specdb::NmrOneD 144836 Specdb::NmrOneD 144837 Specdb::NmrOneD 144838 Specdb::NmrOneD 144839 Specdb::NmrOneD 144840 Specdb::NmrOneD 144841 Specdb::NmrOneD 144842 Specdb::NmrOneD 144843 Specdb::NmrOneD 144844 Specdb::NmrOneD 144845 Specdb::NmrOneD 144846 Specdb::NmrOneD 144847 Specdb::NmrOneD 144848 Specdb::NmrOneD 144849 Specdb::NmrOneD 166492 Adipose Tissue 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 Adrenal Medulla 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 Bladder 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 Blood Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles. Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28. 22370585 Blood 107.2 uM Detected by GC/MS Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan 2. 17197001 Blood Detected by NMR Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22. 25913299 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 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 Blood 205-264 uM Ion exchange chromatography with fluorometric detection Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x. 11204708 Blood 132.6 uM Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73. 9374324 Blood 90-117 uM Chromatography with spectrophotometric detection Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7. 3535614 Blood 212 +/- 24 uM By LC-MS/MS & 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 67-1877 uM By LC-MS/MS Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017. 28453535 Blood 152-162 uM By HPLC Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010. 28036059 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 Colostrum Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle. D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub 2012 Feb 21. 22361340 Epidermis 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 Fibroblasts 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 Intestine 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 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 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 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 Liver 426 +/- 117 nmol/g of tissue By LC-MS/MS & 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 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Longissimus Thoracis Muscle 154 +/- 37 nmol/g of tissue By LC-MS/MS & 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 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 4.64 +/- 1.55 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 2 - 22 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 25919.988 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 25919.988 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 25919.988 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 25919.988 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 25157.635 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 25157.635 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 25157.635 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 3.80 +/- 1.31 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 6.8 +/- 0.5 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 4.9 +/- 0.4 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 5.5 +/- 0.5 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 6.3 +/- 1.4 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 3.81 +/- 0.83 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 Muscle Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle. D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub 2012 Feb 21. 22361340 Muscle 138.21 +/- 19.52 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 150.85 +/- 24.51 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 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 80-424 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 390.39 +/- 33.32 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 770 nmol/g of tissue By NMR Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep 26. 26437054 Muscle 7100 +/- 1140 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 8630 +/- 1800 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 1860 +/- 400 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 4030 +/- 990 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 86.05 +/- 6.13 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 180-256 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 Muscle 238-960 nmol/g of tissue By CE-TOFMS Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648. Epub 2019 Jan 4. 30744349 Neuron 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 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 Platelet 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 Prostate Tissue 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 Ruminal Fluid 119.2 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 182.8 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 191.3 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 125.8 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 125.79 +/- 5.98 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 76-571 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 70-159 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 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 119 +/- 17 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 183 +/- 76 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 191 +/- 44 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 146 +/- 46 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. Ruminal Fluid 145 +/- 46 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and DFI-MS/MS. 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 603 +/- 119 uM By LC-MS/MS & 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 99.2 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 164 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 155 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 109 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 Semen From 5 bulls Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x. 5096119 Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was authenticated by external standard reference(s). Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 Semimembranosus Muscle 158 +/- 33 nmol/g of tissue By LC-MS/MS & 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 40 nmol/g of tissue By chromatography with spectrophotometric detection Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x. 5096119 Testis 138 +/- 23 nmol/g of tissue By LC-MS/MS & 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 DB00149 FDB000899 C00123 5880 15603 6106 LEU C00001377 33942 Leucine 24 Leuchtenberger, Wolfgang; Karrenbauer, Michael; Ploecker, Ulf. Scale-up of an enzyme membrane reactor process for the manufacture of L-enantiomeric compounds. Annals of the New York Academy of Sciences (1984), 434(Enzyme Eng.), 78-86. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en BMDBP00226 Branched-chain-amino-acid aminotransferase A4IFQ7 BCAT1 Enzyme BMDBP00227 Branched-chain-amino-acid aminotransferase, mitochondrial Q5EA40 BCAT2 Enzyme BMDBP00228 Branched-chain-amino-acid aminotransferase Q0V8J6 BCAT2 Enzyme BMDBP00229 Branched-chain-amino-acid aminotransferase Q5E9U7 BCAT2 Enzyme BMDBP01993 Cyclic AMP-dependent transcription factor ATF-4 Q3ZCH6 ATF4 Enzyme BMDBP02160 Blood-brain barrier large neutral amino acid transporter Q9TU26 SLC7A5 Enzyme