1.0 2016-09-30 22:26:31 UTC 2020-06-04 22:23:45 UTC BMDB0000191 BMDB00191 L-Aspartic acid L-Aspartic acid, also known as Asp or D, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Aspartic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Aspartic acid exists in all living species, ranging from bacteria to humans. L-Aspartic acid has been found to be associated with several diseases known as frontotemporal dementia, pancreatic cancer, cirrhosis, and perillyl alcohol administration for cancer treatment; also l-aspartic acid has been linked to the inborn metabolic disorders including growth hormone deficiency. (S)-2-Aminobutanedioic acid (S)-2-Aminosuccinic acid 2-Aminosuccinic acid Asp ASPARTIC ACID D L-Asparaginsaeure L-Asp (S)-2-Aminobutanedioate (S)-2-Aminosuccinate 2-Aminosuccinate ASPARTate L-Aspartate (+)-Aspartate (+)-Aspartic acid (2S)-Aspartate (2S)-Aspartic acid (L)-Aspartate (L)-Aspartic acid (R)-2-Aminosuccinate (S)-(+)-Aspartate (S)-(+)-Aspartic acid (S)-Amino-butanedioate (S)-Amino-butanedioic acid (S)-Aminobutanedioate (S)-Aminobutanedioic acid (S)-Aspartate (S)-Aspartic acid 2-Amino-3-methylsuccinate 2-Amino-3-methylsuccinic acid alpha-Aminosuccinate alpha-Aminosuccinic acid Aminosuccinate Asparagate Asparagic acid Asparaginate Asparaginic acid Asparatate H-Asp-OH L-(+)-Aspartate L-(+)-Aspartic acid L-Aminosuccinate L-Aminosuccinic acid L-Asparagate L-Asparagic acid L-Asparaginate L-Asparaginic acid (+-)-Aspartic acid (R,S)-Aspartic acid Aspartate, disodium Aspartate, magnesium Aspartate, monopotassium Aspartic acid, dipotassium salt Aspartic acid, hydrobromide Aspartic acid, monopotassium salt Aspartic acid, monosodium salt Aspartic acid, potassium salt L Aspartate MG5Longoral Potassium aspartate Polysuccinimide Ammonium aspartate Aspartate, ammonium Aspartate, calcium Aspartate, monosodium Aspartic acid, calcium salt Aspartic acid, disodium salt Aspartic acid, magnesium (1:1) salt, hydrochloride, trihydrate Dipotassium aspartate Disodium aspartate Hydrochloride, aspartate magnesium Monopotassium aspartate Sodium aspartate Aspartate, dipotassium Aspartic acid, magnesium (2:1) salt Aspartic acid, sodium salt Hydrobromide aspartic acid Magnesium aspartate MG 5 Longoral Monosodium aspartate Aspartate magnesium hydrochloride Aspartate, potassium Aspartate, sodium Aspartic acid, ammonium salt Aspartic acid, hydrochloride Aspartic acid, magnesium-potassium (2:1:2) salt Calcium aspartate Hydrochloride aspartic acid L Aspartic acid Magnesiocard MG-5-Longoral Poly-DL-succinimide C4H7NO4 133.1027 133.037507717 (2S)-2-aminobutanedioic acid L-aspartic acid 56-84-8 N[C@@H](CC(O)=O)C(O)=O InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1 CKLJMWTZIZZHCS-REOHCLBHSA-N belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid 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 Aspartic acid and derivatives Amino acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Fatty acids and conjugates Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Aspartic acid or derivatives Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative L-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds Amino acids Common amino acids L-alpha-amino acid aspartate family amino acid aspartic acid proteinogenic amino acid Solid melting_point 270 °C water_solubility 5.39 mg/mL YALKOWSKY,SH & DANNENFELSER,RM (1992) logp -3.89 CHMELIK,J ET AL. (1991) logp -3.52 ALOGPS logs 0.03 ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 1.7 ChemAxon pka_strongest_basic 9.61 ChemAxon iupac (2S)-2-aminobutanedioic acid ChemAxon average_mass 133.1027 ChemAxon mono_mass 133.037507717 ChemAxon smiles N[C@@H](CC(O)=O)C(O)=O ChemAxon formula C4H7NO4 ChemAxon inchi InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1 ChemAxon inchikey CKLJMWTZIZZHCS-REOHCLBHSA-N ChemAxon polar_surface_area 100.62 ChemAxon refractivity 26.53 ChemAxon polarizability 11.28 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 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 Ammonia Recycling SMP0087177 Arginine and Proline Metabolism SMP0087178 Aspartate Metabolism SMP0087165 beta-Alanine Metabolism SMP0087180 Glutamate Metabolism SMP0087169 Malate-Aspartate Shuttle SMP0087204 Protein Synthesis: Aspartic Acid SMP0119386 Purine Metabolism SMP0087239 Tyrosine Metabolism SMP0087235 Urea Cycle SMP0087224 Specdb::NmrTwoD 990 Specdb::NmrTwoD 1196 Specdb::MsIr 279 Specdb::MsIr 280 Specdb::MsIr 281 Specdb::NmrOneD 1164 Specdb::NmrOneD 1199 Specdb::NmrOneD 4995 Specdb::NmrOneD 6092 Specdb::NmrOneD 6093 Specdb::NmrOneD 6094 Specdb::NmrOneD 6095 Specdb::NmrOneD 6096 Specdb::NmrOneD 6097 Specdb::NmrOneD 6098 Specdb::NmrOneD 6099 Specdb::NmrOneD 6100 Specdb::NmrOneD 6101 Specdb::NmrOneD 6102 Specdb::NmrOneD 6103 Specdb::NmrOneD 6104 Specdb::NmrOneD 6105 Specdb::NmrOneD 6106 Specdb::NmrOneD 6107 Specdb::NmrOneD 6108 Specdb::NmrOneD 6109 Specdb::NmrOneD 6110 Specdb::NmrOneD 6111 Specdb::NmrOneD 166470 Specdb::CMs 435 Specdb::CMs 436 Specdb::CMs 437 Specdb::CMs 438 Specdb::CMs 439 Specdb::CMs 440 Specdb::CMs 1130 Specdb::CMs 1205 Specdb::CMs 1395 Specdb::CMs 2688 Specdb::CMs 30054 Specdb::CMs 30200 Specdb::CMs 30303 Specdb::CMs 30304 Specdb::CMs 30305 Specdb::CMs 30484 Specdb::CMs 30733 Specdb::CMs 30883 Specdb::CMs 31058 Specdb::CMs 31059 Specdb::CMs 31060 Specdb::CMs 37347 Specdb::CMs 173357 Specdb::CMs 1053849 Specdb::CMs 1053850 Specdb::MsMs 304 Specdb::MsMs 305 Specdb::MsMs 306 Specdb::MsMs 3473 Specdb::MsMs 3474 Specdb::MsMs 3475 Specdb::MsMs 3476 Specdb::MsMs 3477 Specdb::MsMs 3478 Specdb::MsMs 3479 Specdb::MsMs 3480 Specdb::MsMs 3481 Specdb::MsMs 3482 Specdb::MsMs 3483 Specdb::MsMs 3484 Specdb::MsMs 3485 Specdb::MsMs 3486 Specdb::MsMs 3487 Specdb::MsMs 3488 Specdb::MsMs 3489 Specdb::MsMs 3490 Specdb::MsMs 3491 Specdb::MsMs 3492 Specdb::MsMs 3493 Specdb::MsMs 3494 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 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 14.5-16 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 31.9 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 31-36 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 4.2-4.8 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 24 +/- 11 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 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 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 384 +/- 165 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 70 +/- 28 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 Milk 21787.687 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 21787.687 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 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 Milk 21787.687 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 21787.687 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 28.86 +/- 11.37 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 21036.388 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 21036.388 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 21036.388 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 10 - 77 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 19 +/- 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 20 +/- 2 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 20 +/- 1 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 19 +/- 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 19 +/- 3 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 21 +/- 2 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 19 +/- 3 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 21 +/- 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 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 Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk 28.63 +/- 13.11 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 20.35 +/- 7.08 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 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 26560 +/- 2480 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 26530 +/- 2600 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 24230 +/- 2800 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 25930 +/- 2200 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 14-54 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 153-925 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 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 122 +/- 35 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 185 +/- 50 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 180 +/- 69 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 115 +/- 47 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 115 +/- 47 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 68-228 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 164 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 201 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 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 123 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 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 157 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 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 132.7 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 196.4 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 179.6 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 126 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 124.71 +/- 40.5 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 566 +/- 204 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 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 57 +/- 28 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 310-550 nmol/g of tissue By paper chromatography with spectrophotometric detection Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415. 4429492 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 Testis 597 +/- 215 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 C00049 FDB012567 DB00128 5960 5745 17053 C00001342 L-ASPARTATE Aspartic acid 33663 5206 Pamfil, Maria; Lupescu, Irina; Savoiu, Valeria Gabriela. L-aspartic acid production from fumarate using Escherichia coli whole cells. Rom. (2005), 3pp. 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 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 Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 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 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 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 BMDBP00237 Argininosuccinate synthase P14568 ASS1 Enzyme BMDBP00495 Adenylosuccinate synthetase isozyme 1 A5PJR4 ADSS1 Enzyme BMDBP00525 Adenylosuccinate synthetase isozyme 2 A7MBG0 ADSS2 Enzyme BMDBP00562 Aspartoacylase P46446 ASPA Enzyme BMDBP00563 Asparagine synthetase [glutamine-hydrolyzing] Q1LZA3 ASNS Enzyme BMDBP00564 Aspartate--tRNA ligase, cytoplasmic Q3SYZ4 DARS1 Enzyme BMDBP00565 Isoaspartyl peptidase/L-asparaginase Q32LE5 ASRGL1 Enzyme BMDBP00566 Aspartyl aminopeptidase Q2HJH1 DNPEP Enzyme BMDBP00567 Aspartate aminotransferase, cytoplasmic P33097 GOT1 Enzyme BMDBP00568 Aspartyl/asparaginyl beta-hydroxylase Q28056 ASPH Enzyme BMDBP00569 Aspartate aminotransferase, mitochondrial P12344 GOT2 Enzyme BMDBP00570 Aspartate--tRNA ligase, mitochondrial A6QPU5 DARS2 Enzyme BMDBP00571 Putative aspartate aminotransferase, cytoplasmic 2 Q2T9S8 GOT1L1 Enzyme BMDBP00572 Glutamyl aminopeptidase Q32LQ0 ENPEP Enzyme BMDBP00862 Glutamate decarboxylase 1 Q0VCA1 GAD1 Enzyme BMDBP01814 Mitochondrial 2-oxoglutarate/malate carrier protein P22292 SLC25A11 Enzyme BMDBP02848 Interleukin 4 induced 1 F1N191 IL4I1 Enzyme BMDBP02849 Carbamoyl-phosphate synthetase 2, aspartate transcarbamylase, and dihydroorotase F1MVC0 CAD Enzyme BMDBP02938 Phosphoribosylaminoimidazole carboxylase, phosphoribosylaminoimidazole succinocarboxamide synthetase Q2HJ26 PAICS Enzyme