1.0 2016-09-30 22:20:20 UTC 2020-06-04 21:58:33 UTC BMDB0000159 BMDB00159 L-Phenylalanine L-Phenylalanine, also known as F or endorphenyl, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Phenylalanine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Phenylalanine exists in all living species, ranging from bacteria to humans. L-Phenylalanine is a potentially toxic compound. (S)-2-Amino-3-phenylpropionic acid (S)-alpha-Amino-beta-phenylpropionic acid 3-Phenyl-L-alanine beta-Phenyl-L-alanine F Phe PHENYLALANINE (S)-2-Amino-3-phenylpropionate (S)-a-Amino-b-phenylpropionate (S)-a-Amino-b-phenylpropionic acid (S)-alpha-Amino-beta-phenylpropionate (S)-Α-amino-β-phenylpropionate (S)-Α-amino-β-phenylpropionic acid b-Phenyl-L-alanine Β-phenyl-L-alanine (-)-beta-Phenylalanine (L)-Phenylalanine (S)-(-)-Phenylalanine (S)-2-Amino-3-phenylpropanoate (S)-2-Amino-3-phenylpropanoic acid (S)-alpha-Amino-benzenepropanoate (S)-alpha-Amino-benzenepropanoic acid (S)-alpha-Aminobenzenepropanoate (S)-alpha-Aminobenzenepropanoic acid (S)-alpha-Aminohydrocinnamate (S)-alpha-Aminohydrocinnamic acid (S)-Phenylalanine alpha-Aminohydrocinnamate alpha-Aminohydrocinnamic acid beta-Phenyl-alpha-alanine beta-Phenylalanine L-2-Amino-3-phenylpropionate L-2-Amino-3-phenylpropionic acid Phenyl-alanine Phenylalamine L-Isomer phenylalanine Phenylalanine, L isomer Phenylalanine, L-isomer Endorphenyl (6S)-Tetrahydrofolate (6S)-Tetrahydrofolic acid (6S)-THFA 5,6,7,8-Tetrahydrofolate Tetrahydrofolate THF 5,6,7,8-Tetrahydrofolic acid C9H11NO2 165.1891 165.078978601 (2S)-2-amino-3-phenylpropanoic acid L-phenylalanine 63-91-2 N[C@@H](CC1=CC=CC=C1)C(O)=O InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1 COLNVLDHVKWLRT-QMMMGPOBSA-N belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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 Phenylalanine and derivatives Amino acids Amphetamines and derivatives Aralkylamines Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Phenylpropanoic acids 3-phenylpropanoic-acid Alpha-amino acid Amine Amino acid Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalanine or derivatives Primary aliphatic amine Primary amine Aromatic homomonocyclic compounds Common amino acids L-alpha-amino acid erythrose 4-phosphate/phosphoenolpyruvate family amino acid phenylalanine proteinogenic amino acid Solid melting_point 283 °C water_solubility 26.9 mg/mL logp -1.38 AVDEEF,A (1997) logp -1.35 ALOGPS logs -1.60 ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 2.47 ChemAxon pka_strongest_basic 9.45 ChemAxon iupac (2S)-2-amino-3-phenylpropanoic acid ChemAxon average_mass 165.1891 ChemAxon mono_mass 165.078978601 ChemAxon smiles N[C@@H](CC1=CC=CC=C1)C(O)=O ChemAxon formula C9H11NO2 ChemAxon inchi InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1 ChemAxon inchikey COLNVLDHVKWLRT-QMMMGPOBSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 45.12 ChemAxon polarizability 17.03 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 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Phenylalanine and Tyrosine Metabolism SMP0087218 Protein Synthesis: Phenylalanine SMP0119406 Specdb::EiMs 1975 Specdb::MsIr 8 Specdb::MsIr 25 Specdb::MsIr 243 Specdb::MsIr 244 Specdb::MsIr 245 Specdb::NmrOneD 1118 Specdb::NmrOneD 1177 Specdb::NmrOneD 142590 Specdb::NmrOneD 142591 Specdb::NmrOneD 142592 Specdb::NmrOneD 142593 Specdb::NmrOneD 142594 Specdb::NmrOneD 142595 Specdb::NmrOneD 142596 Specdb::NmrOneD 142597 Specdb::NmrOneD 142598 Specdb::NmrOneD 142599 Specdb::NmrOneD 142600 Specdb::NmrOneD 142601 Specdb::NmrOneD 142602 Specdb::NmrOneD 142603 Specdb::NmrOneD 142604 Specdb::NmrOneD 142605 Specdb::NmrOneD 142606 Specdb::NmrOneD 142607 Specdb::NmrOneD 142608 Specdb::NmrOneD 142609 Specdb::NmrOneD 166451 Specdb::MsMs 248 Specdb::MsMs 249 Specdb::MsMs 250 Specdb::MsMs 3191 Specdb::MsMs 3192 Specdb::MsMs 3193 Specdb::MsMs 3194 Specdb::MsMs 3195 Specdb::MsMs 3196 Specdb::MsMs 3197 Specdb::MsMs 3198 Specdb::MsMs 3199 Specdb::MsMs 3200 Specdb::MsMs 3201 Specdb::MsMs 3202 Specdb::MsMs 3203 Specdb::MsMs 3204 Specdb::MsMs 3205 Specdb::MsMs 3206 Specdb::MsMs 3207 Specdb::MsMs 3208 Specdb::MsMs 3209 Specdb::MsMs 3210 Specdb::MsMs 3211 Specdb::MsMs 3212 Specdb::CMs 389 Specdb::CMs 390 Specdb::CMs 391 Specdb::CMs 1252 Specdb::CMs 1304 Specdb::CMs 2830 Specdb::CMs 30069 Specdb::CMs 30210 Specdb::CMs 30607 Specdb::CMs 30732 Specdb::CMs 30771 Specdb::CMs 31032 Specdb::CMs 31033 Specdb::CMs 37329 Specdb::CMs 138002 Specdb::CMs 145736 Specdb::CMs 1051754 Specdb::CMs 1051755 Specdb::CMs 1051757 Specdb::NmrTwoD 975 Specdb::NmrTwoD 1177 All Tissues 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 47.3 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 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 50.7 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 65-75 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 44-58 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 71 +/- 7 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 45-48 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 Blood Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years. Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047 doi: 10.1007/s11306-013-0520-2 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 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 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 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 138 +/- 22 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 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 Longissimus Thoracis Muscle 55 +/- 12 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 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 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 Milk 10896.603 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 10896.603 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 10896.603 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 10896.603 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 10291.236 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 10291.236 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 10291.236 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 2 - 10 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 1.7 +/- 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 1.9 +/- 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 1.9 +/- 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 1.99 +/- 0.01 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 3.4 +/- 0.3 uM Raw milk from Simmental cows during late lactation Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug 23. 23931703 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 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 105.7 +/- 18.05 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 242.58 +/- 15.65 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 51-258 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 54.02 +/- 3.36 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 240 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 Detected by NMR in beef muscle (longissimus dorsi). 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 80.81 +/- 10.96 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 36-48 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 103-496 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 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 36 +/- 13 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 64 +/- 17 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 65 +/- 20 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 34 +/- 17 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 34 +/- 17 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, 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 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 31-80 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 35.7 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 64.5 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 77.7 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 28.9 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 17 - 29 uM Wadud S, Onodera R, Or-Rashid MM, Amin MR: Determination of histidine and related compounds in rumen fluid by liquid chromatography. J AOAC Int. 2000 Jan-Feb;83(1):8-15. 10692998 Ruminal Fluid 310 +/- 129 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 35.37 +/- 13.73 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. 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 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 58 +/- 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 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. 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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 BMDBP00389 Phenylalanine-4-hydroxylase Q2KIH7 PAH Enzyme BMDBP00567 Aspartate aminotransferase, cytoplasmic P33097 GOT1 Enzyme BMDBP00859 Tyrosine aminotransferase Q58CZ9 TAT Enzyme BMDBP01278 GTP cyclohydrolase 1 feedback regulatory protein Q32L41 GCHFR Enzyme BMDBP02160 Blood-brain barrier large neutral amino acid transporter Q9TU26 SLC7A5 Enzyme BMDBP02848 Interleukin 4 induced 1 F1N191 IL4I1 Enzyme