2.0 2012-05-31 14:04:20 -0600 2015-06-03 15:54:42 -0600 ECMDB04080 M2MDB000598 2-Hydroxy-3-oxosuccinate 2-hydroxy-3-oxosuccinate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. 2-hydroxy-3-oxosuccinate is invovled in Glyoxylate and dicarboxylate metabolism. (KEGG) 2-Hydroxy-3-oxosuccinic acid Oxaloglycolate Oxaloglycolic acid C4H4O6 148.071 148.00078786 2-hydroxy-3-oxobutanedioic acid oxaloglycolate OC(C(O)=O)C(=O)C(O)=O InChI=1S/C4H4O6/c5-1(3(7)8)2(6)4(9)10/h1,5H,(H,7,8)(H,9,10) RMHHUKGVZFVHED-UHFFFAOYSA-N Cytoplasm Periplasm logp -0.84 ALOGPS logs -0.61 ALOGPS solubility 3.62e+01 g/l ALOGPS logp -0.76 ChemAxon pka_strongest_acidic 2.12 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2-hydroxy-3-oxobutanedioic acid ChemAxon average_mass 148.071 ChemAxon mono_mass 148.00078786 ChemAxon smiles OC(C(O)=O)C(=O)C(O)=O ChemAxon formula C4H4O6 ChemAxon inchi InChI=1S/C4H4O6/c5-1(3(7)8)2(6)4(9)10/h1,5H,(H,7,8)(H,9,10) ChemAxon inchikey RMHHUKGVZFVHED-UHFFFAOYSA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 25.67 ChemAxon polarizability 10.95 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Butanoate metabolism ec00650 Glyoxylate and dicarboxylate metabolism ec00630 glycolate and glyoxylate degradation II Oxaloglycolate (2-Hydroxy-3-oxosuccinate) interacts with a tartrate dehydrogenase resulting in a L-tartrate. L-tartrate then interacts with tartrate dehydrogenase resulting in a Oxaloacetate. Oxaloacetate and acetyl-coa interact to result in a citrate which is processed by a aconitate hydratase resulting in a cis-Aconitate and further more into a isocitrate which will eventually be procressed into a glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase. PW002021 Metabolic Specdb::CMs 99282 Specdb::NmrOneD 281959 Specdb::NmrOneD 281960 Specdb::NmrOneD 281961 Specdb::NmrOneD 281962 Specdb::NmrOneD 281963 Specdb::NmrOneD 281964 Specdb::NmrOneD 281965 Specdb::NmrOneD 281966 Specdb::NmrOneD 281967 Specdb::NmrOneD 281968 Specdb::NmrOneD 281969 Specdb::NmrOneD 281970 Specdb::NmrOneD 281971 Specdb::NmrOneD 281972 Specdb::NmrOneD 281973 Specdb::NmrOneD 281974 Specdb::NmrOneD 281975 Specdb::NmrOneD 281976 Specdb::NmrOneD 281977 Specdb::NmrOneD 281978 Specdb::MsMs 27338 Specdb::MsMs 27339 Specdb::MsMs 27340 Specdb::MsMs 33896 Specdb::MsMs 33897 Specdb::MsMs 33898 524 509 C03459 17778 CPD-66 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 D-malate dehydrogenase [decarboxylating] P76251 DMLA_ECOLI dmlA http://ecmdb.ca/proteins/P76251.xml Meso-Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion R02545 Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion R06180