1.0 2016-09-30 22:26:43 UTC 2020-06-04 20:52:18 UTC BMDB0000208 BMDB00208 Oxoglutaric acid Oxoglutaric acid, also known as oxoglutarate or alpha-ketoglutarate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Oxoglutaric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Oxoglutaric acid exists in all living species, ranging from bacteria to humans. Oxoglutaric acid is a potentially toxic compound. Oxoglutaric acid has been found to be associated with several diseases known as schizophrenia, eosinophilic esophagitis, amish lethal microcephaly, and anoxia; also oxoglutaric acid has been linked to the inborn metabolic disorders including d-2-hydroxyglutaric aciduria. 2-Ketoglutaric acid alpha-Ketoglutaric acid 2-Ketoglutarate a-Ketoglutarate a-Ketoglutaric acid alpha-Ketoglutarate Α-ketoglutarate Α-ketoglutaric acid Oxoglutarate 2-oxo-1,5-Pentanedioate 2-oxo-1,5-Pentanedioic acid 2-Oxoglutarate 2-Oxoglutaric acid 2-Oxopentanedioate 2-Oxopentanedioic acid alpha-Oxoglutarate Oxogluric acid 2 Oxoglutaric acid Ketoglutaric acid alpha Ketoglutaric acid 2 Ketoglutaric acid alpha Ketoglutarate alpha Oxoglutarate 2 Ketoglutarate 2 Oxoglutarate alpha-Oxoglutaric acid alpha-Oxopentanedioic acid alpha-Keto-glutaric acid Α-oxoglutaric acid Α-oxopentanedioic acid Α-keto-glutaric acid C5H6O5 146.0981 146.021523302 2-oxopentanedioic acid oxoglutarate 328-50-7 OC(=O)CCC(=O)C(O)=O InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) KPGXRSRHYNQIFN-UHFFFAOYSA-N belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Organic compounds Organic acids and derivatives Keto acids and derivatives Gamma-keto acids and derivatives Gamma-keto acids and derivatives Alpha-hydroxy ketones Alpha-keto acids and derivatives Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Short-chain keto acids and derivatives Aliphatic acyclic compound Alpha-hydroxy ketone Alpha-keto acid Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Gamma-keto acid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Short-chain keto acid Aliphatic acyclic compounds oxo dicarboxylic acid Solid melting_point 115.5 °C water_solubility 541.5 mg/mL logp -0.60 ALOGPS logs -0.44 ALOGPS logp -0.11 ChemAxon pka_strongest_acidic 2.66 ChemAxon pka_strongest_basic -9.7 ChemAxon iupac 2-oxopentanedioic acid ChemAxon average_mass 146.0981 ChemAxon mono_mass 146.021523302 ChemAxon smiles OC(=O)CCC(=O)C(O)=O ChemAxon formula C5H6O5 ChemAxon inchi InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) ChemAxon inchikey KPGXRSRHYNQIFN-UHFFFAOYSA-N ChemAxon polar_surface_area 91.67 ChemAxon refractivity 28.88 ChemAxon polarizability 12.17 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 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 Alanine Metabolism SMP0087164 Ammonia Recycling SMP0087177 Arginine and Proline Metabolism SMP0087178 Aspartate Metabolism SMP0087165 beta-Alanine Metabolism SMP0087180 Carnitine Synthesis SMP0087187 Citric Acid Cycle SMP0087163 Cysteine Metabolism SMP0087189 Gluconeogenesis SMP0087223 Glucose-Alanine Cycle SMP0087221 Glutamate Metabolism SMP0087169 Glycine and Serine Metabolism SMP0087245 Lysine Degradation SMP0087203 Malate-Aspartate Shuttle SMP0087204 Oxidation of Branched-Chain Fatty Acids SMP0087255 Phenylalanine and Tyrosine Metabolism SMP0087218 Phytanic Acid Peroxisomal Oxidation SMP0087217 Propanoate Metabolism SMP0087248 Succinate Signalling SMP0120941 Tryptophan Metabolism SMP0087237 Tyrosine Metabolism SMP0087235 Urea Cycle SMP0087224 Valine, Leucine, and Isoleucine Degradation SMP0087234 Warburg Effect SMP0087270 Specdb::CMs 464 Specdb::CMs 465 Specdb::CMs 466 Specdb::CMs 1231 Specdb::CMs 1263 Specdb::CMs 2723 Specdb::CMs 30238 Specdb::CMs 30479 Specdb::CMs 30912 Specdb::CMs 31073 Specdb::CMs 31074 Specdb::CMs 31910 Specdb::CMs 37357 Specdb::CMs 146405 Specdb::CMs 1054042 Specdb::CMs 1054043 Specdb::CMs 1054045 Specdb::CMs 1054047 Specdb::CMs 1054048 Specdb::CMs 1054050 Specdb::CMs 1054052 Specdb::CMs 1054054 Specdb::CMs 1054056 Specdb::CMs 1054058 Specdb::CMs 1054059 Specdb::EiMs 998 Specdb::MsIr 296 Specdb::MsIr 297 Specdb::MsIr 298 Specdb::NmrTwoD 1207 Specdb::MsMs 337 Specdb::MsMs 338 Specdb::MsMs 339 Specdb::MsMs 3615 Specdb::MsMs 3616 Specdb::MsMs 3617 Specdb::MsMs 3618 Specdb::MsMs 3619 Specdb::MsMs 3620 Specdb::MsMs 3621 Specdb::MsMs 3622 Specdb::MsMs 3623 Specdb::MsMs 3624 Specdb::MsMs 3625 Specdb::MsMs 3626 Specdb::MsMs 20237 Specdb::MsMs 20238 Specdb::MsMs 20239 Specdb::MsMs 20354 Specdb::MsMs 20355 Specdb::MsMs 20356 Specdb::MsMs 21788 Specdb::MsMs 21789 Specdb::MsMs 21790 Specdb::MsMs 21905 Specdb::NmrOneD 1192 Specdb::NmrOneD 1202 Specdb::NmrOneD 2337 Specdb::NmrOneD 3037 Specdb::NmrOneD 4779 Specdb::NmrOneD 142870 Specdb::NmrOneD 142871 Specdb::NmrOneD 142872 Specdb::NmrOneD 142873 Specdb::NmrOneD 142874 Specdb::NmrOneD 142875 Specdb::NmrOneD 142876 Specdb::NmrOneD 142877 Specdb::NmrOneD 142878 Specdb::NmrOneD 142879 Specdb::NmrOneD 142880 Specdb::NmrOneD 142881 Specdb::NmrOneD 142882 Specdb::NmrOneD 142883 Specdb::NmrOneD 142884 Specdb::NmrOneD 142885 Specdb::NmrOneD 142886 Specdb::NmrOneD 142887 Specdb::NmrOneD 142888 Specdb::NmrOneD 142889 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 117.93 +/- 17.22 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 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 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 104 +/- 7 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 277.1 uM Raw milk Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83. 2760296 Milk 112 +/- 7 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 103 +/- 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 109 +/- 6 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 37 - 156 uM Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. 22098372 Milk 70 - 156 uM Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. 22098372 Milk 240 uM Raw milk Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6. 9891269 Milk 90 uM Raw milk Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2. 11132867 Milk 102 uM Raw milk Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2. 11132867 Milk 116.48 +/- 18.59 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 111.39 +/- 15.62 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 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 Ruminal Fluid 40 +/- 24 uM By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 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 C00026 FDB003361 DB08845 50 30915 51 C00000769 2-KETOGLUTARATE 33565 Alpha-Ketoglutaric_acid 5218 Tanaka, Katsunobu; kimura, Kazu; Yamaguchi, Ken. Fermentative production of a-oxoglutaric acid. U.S. (1973), 4 pp. Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83. 2760296 Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6. 9891269 Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2. 11132867 Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. 22098372 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 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 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 Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. 27236769 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) 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 BMDBP00239 Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q5E9N4 AADAT Enzyme BMDBP00357 L-2-hydroxyglutarate dehydrogenase, mitochondrial A7MBI3 L2HGDH Enzyme BMDBP00448 Isocitrate dehydrogenase [NADP], mitochondrial Q04467 IDH2 Enzyme BMDBP00454 Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial Q58CP0 IDH3G Enzyme BMDBP00471 Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial O77784 IDH3B Enzyme BMDBP00516 Isocitrate dehydrogenase [NADP] cytoplasmic Q9XSG3 IDH1 Enzyme BMDBP00521 Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial P41563 IDH3A Enzyme BMDBP00567 Aspartate aminotransferase, cytoplasmic P33097 GOT1 Enzyme BMDBP00568 Aspartyl/asparaginyl beta-hydroxylase Q28056 ASPH Enzyme BMDBP00569 Aspartate aminotransferase, mitochondrial P12344 GOT2 Enzyme BMDBP00571 Putative aspartate aminotransferase, cytoplasmic 2 Q2T9S8 GOT1L1 Enzyme BMDBP00595 Hydroxyacid-oxoacid transhydrogenase, mitochondrial A6QP15 ADHFE1 Enzyme BMDBP00596 4-aminobutyrate aminotransferase, mitochondrial Q9BGI0 ABAT Enzyme BMDBP00622 Trimethyllysine dioxygenase, mitochondrial Q0VC74 TMLHE Enzyme BMDBP00631 Alpha-aminoadipic semialdehyde synthase, mitochondrial A8E657 AASS Enzyme BMDBP00668 Prolyl 4-hydroxylase subunit alpha-1 Q1RMU3 P4HA1 Enzyme BMDBP00682 Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1 O77588 PLOD1 Enzyme BMDBP00688 Phytanoyl-CoA dioxygenase, peroxisomal O18778 PHYH Enzyme BMDBP00691 Prolyl 4-hydroxylase subunit alpha-3 Q75UG4 P4HA3 Enzyme BMDBP00800 D-2-hydroxyglutarate dehydrogenase, mitochondrial Q1JPD3 D2HGDH Enzyme BMDBP00855 Phosphoserine aminotransferase A6QR28 PSAT1 Enzyme BMDBP00856 Glutamate dehydrogenase 1, mitochondrial P00366 GLUD1 Enzyme BMDBP00858 Alanine aminotransferase 1 A4IFH5 GPT Enzyme BMDBP00859 Tyrosine aminotransferase Q58CZ9 TAT Enzyme BMDBP00861 Kynurenine--oxoglutarate transaminase 3 Q0P5G4 KYAT3 Enzyme BMDBP01072 D-3-phosphoglycerate dehydrogenase Q5EAD2 PHGDH Enzyme BMDBP01073 2-oxoglutarate dehydrogenase, mitochondrial Q148N0 OGDH Enzyme BMDBP01327 Ornithine aminotransferase, mitochondrial Q3ZCF5 OAT Enzyme BMDBP01814 Mitochondrial 2-oxoglutarate/malate carrier protein P22292 SLC25A11 Enzyme BMDBP02540 Solute carrier family 25 (Mitochondrial carrier; oxoglutarate carrier), member 11 A5D954 SLC25A11 Enzyme BMDBP02858 Glutamyl-tRNA synthetase 2, mitochondrial G3N260 EARS2 Enzyme