2.0 2012-05-31 13:00:27 -0600 2015-09-13 12:56:08 -0600 ECMDB00694 M2MDB000173 L-2-Hydroxyglutaric acid L-2-hydroxyglutaric acid is a member of the chemical class known as Short-chain Hydroxy Acids and Derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. L-2-Hydroxyglutaric acid (2-hydroxyglutaric acid) is an alpha hydroxy acid. In bacteria it is formed by a 2-hydroxyglutarate synthase (EC 2.3.3.11) and oxidized by 2-hydroxyglutarate oxidase. (Wikipedia, PMID 14491016) (2S)-2-hydroxypentanedioate (2S)-2-hydroxypentanedioic acid (<i>S</i>)-2-hydroxyglutaric acid (S)-2-Hydroxyglutarate (S)-2-Hydroxyglutaric acid (S)-a-Hydroxyglutarate (S)-a-Hydroxyglutaric acid (S)-alpha-Hydroxyglutarate (S)-alpha-Hydroxyglutaric acid (S)-α-Hydroxyglutarate (S)-α-Hydroxyglutaric acid 2-Hydroxy-(S)-Pentanedioate 2-Hydroxy-(S)-Pentanedioic acid 2-Hydroxy-L-Glutarate 2-Hydroxy-L-Glutaric acid L-2-Hydroxyglutarate L-2-hydroxyglutaric acid L-a-Hydroxyglutarate L-a-Hydroxyglutaric acid L-alpha-Hydroxyglutarate L-alpha-Hydroxyglutaric acid L-α-Hydroxyglutarate L-α-Hydroxyglutaric acid C5H8O5 148.114 148.037173366 (2S)-2-hydroxypentanedioic acid L-2-hydroxyglutaric acid 13095-48-2 [H][C@](O)(CCC(O)=O)C(O)=O InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m0/s1 HWXBTNAVRSUOJR-VKHMYHEASA-N Cytoplasm Periplasm logp -1.04 ALOGPS logs 0.03 ALOGPS solubility 1.57e+02 g/l ALOGPS logp -0.82 ChemAxon pka_strongest_acidic 3.28 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac (2S)-2-hydroxypentanedioic acid ChemAxon average_mass 148.114 ChemAxon mono_mass 148.037173366 ChemAxon smiles [H][C@](O)(CCC(O)=O)C(O)=O ChemAxon formula C5H8O5 ChemAxon inchi InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m0/s1 ChemAxon inchikey HWXBTNAVRSUOJR-VKHMYHEASA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 29.63 ChemAxon polarizability 12.97 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 132175 Specdb::CMs 139909 Specdb::CMs 1072465 Specdb::CMs 1072467 Specdb::CMs 1072469 Specdb::CMs 1072470 Specdb::CMs 1072472 Specdb::CMs 1072473 Specdb::CMs 1072475 Specdb::CMs 1072477 Specdb::CMs 1072479 Specdb::CMs 1072480 Specdb::CMs 1072482 Specdb::CMs 1072484 Specdb::CMs 1072486 Specdb::CMs 1072488 Specdb::NmrOneD 1482 Specdb::NmrOneD 144910 Specdb::NmrOneD 144911 Specdb::NmrOneD 144912 Specdb::NmrOneD 144913 Specdb::NmrOneD 144914 Specdb::NmrOneD 144915 Specdb::NmrOneD 144916 Specdb::NmrOneD 144917 Specdb::NmrOneD 144918 Specdb::NmrOneD 144919 Specdb::NmrOneD 144920 Specdb::NmrOneD 144921 Specdb::NmrOneD 144922 Specdb::NmrOneD 144923 Specdb::NmrOneD 144924 Specdb::NmrOneD 144925 Specdb::NmrOneD 144926 Specdb::NmrOneD 144927 Specdb::NmrOneD 144928 Specdb::NmrOneD 144929 Specdb::NmrOneD 166350 Specdb::NmrOneD 166553 Specdb::MsMs 964 Specdb::MsMs 965 Specdb::MsMs 1307377 Specdb::MsMs 1307378 Specdb::MsMs 1307379 Specdb::MsMs 1421887 Specdb::MsMs 1421888 Specdb::MsMs 1421889 Specdb::MsMs 2236993 Specdb::MsMs 2238538 Specdb::MsMs 2239057 Specdb::MsMs 2336557 Specdb::MsMs 2336558 Specdb::MsMs 2336559 Specdb::MsMs 2629961 Specdb::MsMs 2629962 Specdb::MsMs 2629963 Specdb::NmrTwoD 1428 HMDB00694 388969 C03196 16782 CPD-381 S2G 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 REEVES, H. C., AJL, S. J. (1962). "Alpha-hydroxyglutaric acid synthetase." J Bacteriol 84:186-187. 14491016 http://hmdb.ca/system/metabolites/msds/000/000/613/original/HMDB00694.pdf?1358462336 L-2-Hydroxyglutaric acid + Oxygen > Oxoglutaric acid + Hydrogen peroxide RXN0-5364