1.0 2016-09-30 22:35:03 UTC 2020-06-04 21:42:04 UTC BMDB0000696 BMDB00696 L-Methionine L-Methionine, also known as liquimeth or pedameth, belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Methionine is a drug which is used for protein synthesis including the formation of same, l-homocysteine, l-cysteine, taurine, and sulfate. L-Methionine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Methionine exists in all living species, ranging from bacteria to humans. L-Methionine is a potentially toxic compound. (2S)-2-Amino-4-(methylsulfanyl)butanoic acid (S)-2-Amino-4-(methylthio)butanoic acid (S)-2-Amino-4-(methylthio)butyric acid (S)-Methionine L-(-)-Methionine L-alpha-Amino-gamma-methylmercaptobutyric acid L-Methionin M Met METHIONINE L-2-Amino-4methylthiobutyric acid L-Methionine Z (2S)-2-Amino-4-(methylsulfanyl)butanoate (2S)-2-Amino-4-(methylsulphanyl)butanoate (2S)-2-Amino-4-(methylsulphanyl)butanoic acid (S)-2-Amino-4-(methylthio)butanoate (S)-2-Amino-4-(methylthio)butyrate L-a-Amino-g-methylmercaptobutyrate L-a-Amino-g-methylmercaptobutyric acid L-alpha-Amino-gamma-methylmercaptobutyrate L-Α-amino-γ-methylmercaptobutyrate L-Α-amino-γ-methylmercaptobutyric acid L-2-Amino-4methylthiobutyrate (L)-Methionine (S)-(+)-Methionine (S)-2-Amino-4-(methylthio)-butanoate (S)-2-Amino-4-(methylthio)-butanoic acid 2-Amino-4-(methylthio)butyrate 2-Amino-4-(methylthio)butyric acid 2-Amino-4-methylthiobutanoate 2-Amino-4-methylthiobutanoic acid a-Amino-g-methylmercaptobutyrate a-Amino-g-methylmercaptobutyric acid Acimethin alpha-Amino-alpha-aminobutyric acid alpha-Amino-gamma-methylmercaptobutyrate alpha-Amino-gamma-methylmercaptobutyric acid Cymethion g-Methylthio-a-aminobutyrate g-Methylthio-a-aminobutyric acid gamma-Methylthio-alpha-aminobutyrate gamma-Methylthio-alpha-aminobutyric acid H-Met-H H-Met-OH L(-)-Amino-alpha-amino-alpha-aminobutyric acid L(-)-Amino-gamma-methylthiobutyric acid L-2-Amino-4-(methylthio)butyric acid L-2-Amino-4-methylthiobutyric acid L-a-Amino-g-methylthiobutyrate L-a-Amino-g-methylthiobutyric acid L-alpha-Amino-gamma-methylthiobutyrate L-alpha-Amino-gamma-methylthiobutyric acid L-gamma-Methylthio-alpha-aminobutyric acid L-Methioninum Liquimeth Mepron Methilanin Methioninum Metionina Neo-methidin Poly-L-methionine Polymethionine S-Methionine S-Methyl-L-homocysteine Toxin war L-Isomer methionine Methionine, L-isomer Pedameth Methionine, L isomer (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol Bo-xan e 161b Xanthophyll (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol C5H11NO2S 149.211 149.051049291 (2S)-2-amino-4-(methylsulfanyl)butanoic acid L-methionine 63-68-3 CSCC[C@H](N)C(O)=O InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 FFEARJCKVFRZRR-BYPYZUCNSA-N belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine 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 Methionine and derivatives Amino acids Carbonyl compounds Carboxylic acids Dialkylthioethers Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Sulfenyl compounds Thia fatty acids Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Dialkylthioether Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Methionine or derivatives Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Sulfenyl compound Thia fatty acid Thioether Aliphatic acyclic compounds Common amino acids L-alpha-amino acid aspartate family amino acid methionine proteinogenic amino acid Solid melting_point 284 °C water_solubility 56.6 mg/mL YALKOWSKY,SH & DANNENFELSER,RM (1992) logp -1.87 HANSCH,C ET AL. (1995) logp -1.85 ALOGPS logs -0.80 ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 2.53 ChemAxon pka_strongest_basic 9.5 ChemAxon iupac (2S)-2-amino-4-(methylsulfanyl)butanoic acid ChemAxon average_mass 149.211 ChemAxon mono_mass 149.051049291 ChemAxon smiles CSCC[C@H](N)C(O)=O ChemAxon formula C5H11NO2S ChemAxon inchi InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 ChemAxon inchikey FFEARJCKVFRZRR-BYPYZUCNSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 37.59 ChemAxon polarizability 15.5 ChemAxon rotatable_bond_count 4 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 Betaine Metabolism SMP0087182 Glycine and Serine Metabolism SMP0087245 Methionine Metabolism SMP0087249 Protein Synthesis: Methionine SMP0119405 Spermidine and Spermine Biosynthesis SMP0087213 Specdb::MsIr 751 Specdb::MsIr 752 Specdb::MsIr 753 Specdb::NmrTwoD 1031 Specdb::NmrTwoD 1430 Specdb::CMs 615 Specdb::CMs 616 Specdb::CMs 617 Specdb::CMs 1109 Specdb::CMs 1204 Specdb::CMs 2922 Specdb::CMs 30046 Specdb::CMs 30208 Specdb::CMs 30604 Specdb::CMs 30730 Specdb::CMs 30770 Specdb::CMs 31197 Specdb::CMs 31198 Specdb::CMs 37701 Specdb::CMs 170485 Specdb::CMs 1072495 Specdb::CMs 1072497 Specdb::CMs 1072499 Specdb::MsMs 969 Specdb::MsMs 970 Specdb::MsMs 971 Specdb::MsMs 4441 Specdb::MsMs 4442 Specdb::MsMs 4443 Specdb::MsMs 4444 Specdb::MsMs 4445 Specdb::MsMs 4446 Specdb::MsMs 4447 Specdb::MsMs 4448 Specdb::MsMs 4449 Specdb::MsMs 4450 Specdb::MsMs 4451 Specdb::MsMs 4452 Specdb::MsMs 4453 Specdb::MsMs 4454 Specdb::MsMs 4455 Specdb::MsMs 4456 Specdb::MsMs 4457 Specdb::MsMs 4458 Specdb::MsMs 4462 Specdb::MsMs 4463 Specdb::MsMs 179109 Specdb::MsMs 179110 Specdb::NmrOneD 1254 Specdb::NmrOneD 1484 Specdb::NmrOneD 4840 Specdb::NmrOneD 20602 Specdb::NmrOneD 20603 Specdb::NmrOneD 20604 Specdb::NmrOneD 20605 Specdb::NmrOneD 20606 Specdb::NmrOneD 20607 Specdb::NmrOneD 20608 Specdb::NmrOneD 20609 Specdb::NmrOneD 20610 Specdb::NmrOneD 20611 Specdb::NmrOneD 20612 Specdb::NmrOneD 20613 Specdb::NmrOneD 20614 Specdb::NmrOneD 20615 Specdb::NmrOneD 20616 Specdb::NmrOneD 20617 Specdb::NmrOneD 20618 Specdb::NmrOneD 20619 Specdb::NmrOneD 20620 Specdb::NmrOneD 20621 Specdb::NmrOneD 166452 Blood 20.8 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 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 22-29 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 27.9 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 46-52 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 34 +/- 4 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 18-29 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 Blood Detected by DFI-MS/MS (P180) in periparturient Holstein cows. Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13. 24630653 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 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 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 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 54 +/- 16 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 Longissimus Thoracis Muscle 34 +/- 10 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 1.0 +/- 0.1 uM Commercial 1% milk by LC-HRMS 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 0.9 +/- 0.1 uM Commercial 2% milk by LC-HRMS 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 1.0 +/- 0.1 uM Commercial 3.25% milk by LC-HRMS 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 1.0 +/- 0.1 uM Commercial skim milk by LC-HRMS 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 Milk samples collected from 456 Danish Holstein cows 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 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 5897.689 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 5897.689 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 5897.689 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 5897.689 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 5763.65 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 5763.65 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 5763.65 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Muscle 148.53 +/- 22.45 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 151.61 +/- 8.67 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 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 168.81 +/- 20.31 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 262.51 +/- 12.18 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 126-275 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 560 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 990 +/- 140 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 1080 +/- 190 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 790 +/- 100 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 850 +/- 140 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 40-395 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 Pancreas 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 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 24.6 uM By GC-MS. 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 34.6 uM By GC-MS. 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 47.1 uM By GC-MS. 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 Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Ruminal Fluid 20.6 uM By GC-MS. 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 22-53 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 44.0 (27 - 61) uM This concentration measured after 1 hour of feeding.; The three amino acids (AA), threonine, methionine and Lysine were administered intraruminally in mixtures at dosages of 100, 200, 300, and 400 mmol of each,together with polyethylene glycol (PEG) as a liquid marker. Volden H, Velle W, Harstad OM, Aulie A, Sjaastad OV: Apparent ruminal degradation and rumen escape of lysine, methionine, and threonine administered intraruminally in mixtures to high-yielding cows. J Anim Sci. 1998 Apr;76(4):1232-40. 9581948 Ruminal Fluid 22 +/- 8 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 32 +/- 10 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 47 +/- 19 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 19 +/- 10 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 19 +/- 10 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS 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 268 +/- 102 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 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 Semimembranosus Muscle 37 +/- 11 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 Spleen 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 Testis 26 +/- 6 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 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 C00073 DB00134 FDB012683 5907 16643 6137 MET C00001379 Methionine 33753 5664 Boy, Matthias; Klein, Daniela; Schroeder, Hartwig. Method for the production and recovery of methionine. PCT Int. Appl. (2005), 34 pp. 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 BMDBP00174 S-adenosylmethionine synthase A7E3T7 MAT2A Enzyme BMDBP00396 Lipoyl synthase, mitochondrial Q5BIP7 LIAS Enzyme BMDBP00403 S-adenosylmethionine synthase isoform type-1 Q2KJC6 MAT1A Enzyme BMDBP00414 Methionine synthase Q4JIJ3 MTR Enzyme BMDBP00547 Methionine-R-sulfoxide reductase B1 Q3MHL9 MSRB1 Enzyme BMDBP00795 Methionine aminopeptidase 1 A6QLA4 METAP1 Enzyme BMDBP00797 Methionine aminopeptidase 2 Q3ZC89 METAP2 Enzyme BMDBP01057 Betaine--homocysteine S-methyltransferase 1 Q5I597 BHMT Enzyme BMDBP01249 Mitochondrial peptide methionine sulfoxide reductase P54149 MSRA Enzyme BMDBP01250 Methionine--tRNA ligase, mitochondrial A6H7E1 MARS2 Enzyme BMDBP01251 Methionine--tRNA ligase, cytoplasmic Q2T9L8 MARS1 Enzyme BMDBP01585 S-adenosylmethionine mitochondrial carrier protein A6QR09 SLC25A26 Enzyme BMDBP02843 Methionine adenosyltransferase 2 subunit beta Q29RI9 MAT2B Enzyme BMDBP02848 Interleukin 4 induced 1 F1N191 IL4I1 Enzyme BMDBP02980 Peptide-methionine (R)-S-oxide reductase E1BMD3 MSRB3 Enzyme