2.0 2012-05-31 14:08:24 -0600 2015-06-03 15:54:52 -0600 ECMDB06454 M2MDB000671 L-2-Amino-3-oxobutanoic acid L-2-Amino-3-oxobutanoic acid or L-2-amino acetic acid is involved in glycine/serine metabolism and is a breakdown product from glycine. It spontaneously decomposes to aminoacetone. Delta-aminolevuliinate synthase is the enzyme that catalyzes the interconversion between glycine and L-2-amino-3-oxobutanoic acid. Glycine C-acetyltransferase is also capable of catalyzing this reaction. &alpha;-amino-&beta;-ketobutyrate &alpha;-amino-&beta;-ketobutyric acid (2S)-2-amino-3-oxobutanoate (2S)-2-amino-3-oxobutanoic acid (S)-2-Amino-3-oxobutanoate (S)-2-Amino-3-oxobutanoic acid 2-Amino-3-ketobutyrate 2-Amino-3-ketobutyric acid 2-Amino-3-oxobutanoate 2-Amino-3-oxobutanoic acid 2-Amino-3-oxobutyrate 2-Amino-3-oxobutyric acid 2-Amino-acetoacetate 2-Amino-acetoacetic acid a-amino-b-Ketobutyrate a-amino-b-Ketobutyric acid Alpha-Amino-beta-ketobutyrate Alpha-Amino-beta-ketobutyric acid L-2-Amino acetate L-2-Amino acetic acid L-2-Amino-3-oxobutanoate L-2-Amino-3-oxobutanoic acid L-2-Amino-acetoacetate L-2-Amino-acetoacetic acid α-amino-β-Ketobutyrate α-amino-β-Ketobutyric acid C4H7NO3 117.1033 117.042593095 (2S)-2-amino-3-oxobutanoic acid 2-amino-3-ketobutyric acid CC(=O)[C@H](N)C(O)=O InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1 SAUCHDKDCUROAO-VKHMYHEASA-N Solid Cytosol logp -2.63 ALOGPS logs 0.25 ALOGPS solubility 2.06e+02 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 7.25 ChemAxon iupac (2S)-2-amino-3-oxobutanoic acid ChemAxon average_mass 117.1033 ChemAxon mono_mass 117.042593095 ChemAxon smiles CC(=O)[C@H](N)C(O)=O ChemAxon formula C4H7NO3 ChemAxon inchi InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1 ChemAxon inchikey SAUCHDKDCUROAO-VKHMYHEASA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 25.53 ChemAxon polarizability 10.47 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Pyrimidine metabolism The metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate. Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate. 1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate 4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate. PW000942 ec00240 Metabolic Glycine, serine and threonine metabolism ec00260 threonine biosynthesis The biosynthesis of threonine starts with oxalacetic acid interacting with an L-glutamic acid through an aspartate aminotransferase resulting in a oxoglutaric acid and an L-aspartic acid. The latter compound is then phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000817 Metabolic L-threonine degradation to methylglyoxal L-threonine is degrade into methylglyoxal (pyruvaldehyde) by first reacting with a NDA dependent threonine dehydrogenase resulting in the release of a hydrogen ion, an NADH and a 2-amino-3-oxobutanoate. The latter compound reacts spontaneously with a hydrogen ion resulting in the release of a carbon dioxide and a aminoacetone. The aminoacetone in turn reacts with an oxygen and a water molecule through an aminoacetone oxidase resulting in the release of a hydrogen peroxide, ammonium and a methylglyoxal which can then be incorporated in the methylglyoxal degradation pathways. PW002106 Metabolic threonine degradation III (to methylglyoxal) THRDLCTCAT-PWY threonine degradation II THREONINE-DEG2-PWY Specdb::CMs 3283 Specdb::CMs 39014 Specdb::CMs 147271 Specdb::NmrOneD 74432 Specdb::NmrOneD 74433 Specdb::NmrOneD 74434 Specdb::NmrOneD 74435 Specdb::NmrOneD 74436 Specdb::NmrOneD 74437 Specdb::NmrOneD 74438 Specdb::NmrOneD 74439 Specdb::NmrOneD 74440 Specdb::NmrOneD 74441 Specdb::NmrOneD 74442 Specdb::NmrOneD 74443 Specdb::NmrOneD 74444 Specdb::NmrOneD 74445 Specdb::NmrOneD 74446 Specdb::NmrOneD 74447 Specdb::NmrOneD 74448 Specdb::NmrOneD 74449 Specdb::NmrOneD 74450 Specdb::NmrOneD 74451 Specdb::MsMs 23675 Specdb::MsMs 23676 Specdb::MsMs 23677 Specdb::MsMs 30473 Specdb::MsMs 30474 Specdb::MsMs 30475 Specdb::MsMs 2273373 Specdb::MsMs 2273374 Specdb::MsMs 2273375 Specdb::MsMs 3069024 Specdb::MsMs 3069025 Specdb::MsMs 3069026 HMDB06454 5460100 389046 C03508 16944 AMINO-OXOBUT AKB Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 L-threonine 3-dehydrogenase P07913 TDH_ECOLI tdh http://ecmdb.ca/proteins/P07913.xml 2-amino-3-ketobutyrate coenzyme A ligase P0AB77 KBL_ECOLI kbl http://ecmdb.ca/proteins/P0AB77.xml NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG P39831 YDFG_ECOLI ydfG http://ecmdb.ca/proteins/P39831.xml L-Allothreonine + NADP <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADPH NAD + L-Threonine <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADH R01465 THREODEHYD-RXN Acetyl-CoA + Glycine <> L-2-Amino-3-oxobutanoic acid + Coenzyme A R00371 AKBLIG-RXN L-2-Amino-3-oxobutanoic acid + Hydrogen ion > Aminoacetone + Carbon dioxide THREOSPON-RXN Glycine + Acetyl-CoA <> Hydrogen ion + L-2-Amino-3-oxobutanoic acid + Coenzyme A AKBLIG-RXN L-Threonine + NAD > Hydrogen ion + L-2-Amino-3-oxobutanoic acid + NADH THREODEHYD-RXN Acetyl-CoA + Glycine > CoA + L-2-Amino-3-oxobutanoic acid L-Threonine + NAD > L-2-Amino-3-oxobutanoic acid + NADH L-Allothreonine + NADP + L-2-Amino-3-oxobutanoic acid <> Aminoacetone + Carbon dioxide + NADPH + Hydrogen ion R10852 L-Threonine + NAD + L-Threonine > Hydrogen ion + NADH + L-2-Amino-3-oxobutanoic acid PW_R005168 L-2-Amino-3-oxobutanoic acid + Coenzyme A > Acetyl-CoA + Glycine PW_R005169