2.0 2012-05-31 13:55:25 -0600 2015-06-03 15:54:14 -0600 ECMDB02070 M2MDB000436 4-Hydroxy-2-oxoglutaric acid 4-hydroxy-2-oxoglutaric acid is a member of the chemical class known as Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 4-hydroxy-2-oxoglutaric acid is invovled in Glyoxylate and dicarboxylate metabolism. 2-Keto-4-hydroxyglutarate aldolase also plays a role in respiratory metabolic pathways, which suggests a mechanism for respiration resumption during the termination of the SOS response. (PMID 8524853) (+/-)-2-hydroxy-4-oxopentanedioate (+/-)-2-hydroxy-4-oxopentanedioic acid 2-Hydroxy-4-oxopentanedioate 2-Hydroxy-4-oxopentanedioic acid 2-k-4-OH-glutarate 2-k-4-OH-glutaric acid 2-Keto-4-hydroxyglutarate 2-Keto-4-hydroxyglutaric acid 2-Oxo-4-hydroxyglutarate 2-Oxo-4-hydroxyglutaric acid 4-Hydroxy-2-ketoglutarate 4-Hydroxy-2-ketoglutaric acid 4-Hydroxy-2-oxoglutarate 4-Hydroxy-2-oxoglutaric acid D-4-HYDROXY-2-KETO-GLUTARATE D-4-HYDROXY-2-keto-glutaric acid D-4-Hydroxy-2-ketoglutarate D-4-Hydroxy-2-ketoglutaric acid C5H6O6 162.0975 162.016437924 2-hydroxy-4-oxopentanedioic acid 4-hydroxy-2-oxoglutaric acid OC(CC(=O)C(O)=O)C(O)=O InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11) WXSKVKPSMAHCSG-UHFFFAOYSA-N Cytoplasm Periplasm logp -1.11 ALOGPS logs -0.37 ALOGPS solubility 6.98e+01 g/l ALOGPS logp -0.82 ChemAxon pka_strongest_acidic 2.45 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 2-hydroxy-4-oxopentanedioic acid ChemAxon average_mass 162.0975 ChemAxon mono_mass 162.016437924 ChemAxon smiles OC(CC(=O)C(O)=O)C(O)=O ChemAxon formula C5H6O6 ChemAxon inchi InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11) ChemAxon inchikey WXSKVKPSMAHCSG-UHFFFAOYSA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 30.22 ChemAxon polarizability 12.76 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Arginine and proline metabolism ec00330 Glyoxylate and dicarboxylate metabolism ec00630 Metabolic pathways eco01100 Specdb::CMs 2837 Specdb::CMs 38254 Specdb::CMs 146213 Specdb::NmrOneD 148900 Specdb::NmrOneD 148901 Specdb::NmrOneD 148902 Specdb::NmrOneD 148903 Specdb::NmrOneD 148904 Specdb::NmrOneD 148905 Specdb::NmrOneD 148906 Specdb::NmrOneD 148907 Specdb::NmrOneD 148908 Specdb::NmrOneD 148909 Specdb::NmrOneD 148910 Specdb::NmrOneD 148911 Specdb::NmrOneD 148912 Specdb::NmrOneD 148913 Specdb::NmrOneD 148914 Specdb::NmrOneD 148915 Specdb::NmrOneD 148916 Specdb::NmrOneD 148917 Specdb::NmrOneD 148918 Specdb::NmrOneD 148919 Specdb::MsMs 28196 Specdb::MsMs 28197 Specdb::MsMs 28198 Specdb::MsMs 34754 Specdb::MsMs 34755 Specdb::MsMs 34756 Specdb::MsMs 2691626 Specdb::MsMs 2691627 Specdb::MsMs 2691628 Specdb::MsMs 2991140 Specdb::MsMs 2991141 Specdb::MsMs 2991142 HMDB02070 579 C01127 30923 D-4-HYDROXY-2-KETO-GLUTARATE 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 Cayrol, C., Petit, C., Raynaud, B., Capdevielle, J., Guillemot, J. C., Defais, M. (1995). "Recovery of respiration following the SOS response of Escherichia coli requires RecA-mediated induction of 2-keto-4-hydroxyglutarate aldolase." Proc Natl Acad Sci U S A 92:11806-11809. 8524853 KHG/KDPG aldolase P0A955 ALKH_ECOLI eda http://ecmdb.ca/proteins/P0A955.xml 4-Hydroxy-2-oxoglutaric acid <> Pyruvic acid + Glyoxylic acid R00470 4OH2OXOGLUTARALDOL-RXN 4-Hydroxy-2-oxoglutaric acid Glyoxylic acid + Pyruvic acid 4OH2OXOGLUTARALDOL-RXN 4-Hydroxy-2-oxoglutaric acid > Pyruvic acid + Glyoxylic acid