2.0 2012-05-31 10:27:42 -0600 2015-09-13 12:56:08 -0600 ECMDB00606 M2MDB000155 D-2-Hydroxyglutaric acid D-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. (R)-2-hydroxy-Pentanedioate (R)-2-hydroxy-Pentanedioic acid (R)-2-Hydroxyglutarate (R)-2-Hydroxyglutaric acid (R)-a-Hydroxyglutarate (R)-a-Hydroxyglutaric acid (R)-alpha-Hydroxyglutarate (R)-alpha-Hydroxyglutaric acid (R)-α-Hydroxyglutarate (R)-α-Hydroxyglutaric acid 2-Hydroxy-D-Glutarate 2-Hydroxy-D-Glutaric acid D-2-Hydroxyglutarate D-2-Hydroxyglutaric acid D-a-Hydroxyglutarate D-a-Hydroxyglutaric acid D-alpha-Hydroxyglutarate D-alpha-Hydroxyglutaric acid D-α-Hydroxyglutarate D-α-Hydroxyglutaric acid C5H8O5 148.114 148.037173366 2-hydroxypentanedioic acid 2-hydroxyglutaric acid 13095-47-1 OC(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) HWXBTNAVRSUOJR-UHFFFAOYSA-N Cytoplasm Periplasm logp -1.04 ALOGPS logs 0.03 ALOGPS solubility 1.57e+02 g/l ALOGPS melting_point >300 oC logp -0.82 ChemAxon pka_strongest_acidic 3.28 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 2-hydroxypentanedioic acid ChemAxon average_mass 148.114 ChemAxon mono_mass 148.037173366 ChemAxon smiles OC(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) ChemAxon inchikey HWXBTNAVRSUOJR-UHFFFAOYSA-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 Glycine, serine and threonine metabolism ec00260 Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Specdb::CMs 3166 Specdb::CMs 47843 Specdb::CMs 165263 Specdb::NmrOneD 51862 Specdb::NmrOneD 51863 Specdb::NmrOneD 51864 Specdb::NmrOneD 51865 Specdb::NmrOneD 51866 Specdb::NmrOneD 51867 Specdb::NmrOneD 51868 Specdb::NmrOneD 51869 Specdb::NmrOneD 51870 Specdb::NmrOneD 51871 Specdb::NmrOneD 51872 Specdb::NmrOneD 51873 Specdb::NmrOneD 51874 Specdb::NmrOneD 51875 Specdb::NmrOneD 51876 Specdb::NmrOneD 51877 Specdb::NmrOneD 51878 Specdb::NmrOneD 51879 Specdb::NmrOneD 51880 Specdb::NmrOneD 51881 Specdb::MsMs 9152 Specdb::MsMs 9153 Specdb::MsMs 9154 Specdb::MsMs 15824 Specdb::MsMs 15825 Specdb::MsMs 15826 Specdb::MsMs 1470852 Specdb::MsMs 1472478 Specdb::MsMs 1472479 Specdb::MsMs 1472480 Specdb::MsMs 1472481 Specdb::MsMs 1472482 Specdb::MsMs 1472483 Specdb::MsMs 1472484 Specdb::MsMs 1472485 Specdb::MsMs 1472486 Specdb::MsMs 1472487 Specdb::MsMs 1472488 Specdb::MsMs 1472489 Specdb::MsMs 1472490 Specdb::MsMs 1472491 Specdb::MsMs 1472492 Specdb::MsMs 1472493 Specdb::MsMs 1472494 Specdb::MsMs 1472495 HMDB00606 42 C02630 32796 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 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 http://hmdb.ca/system/metabolites/msds/000/000/525/original/HMDB00606.pdf?1358463436 D-3-phosphoglycerate dehydrogenase P0A9T0 SERA_ECOLI serA http://ecmdb.ca/proteins/P0A9T0.xml D-2-Hydroxyglutaric acid + NAD > Oxoglutaric acid + NADH 3-Phospho-D-glycerate + NAD + D-2-Hydroxyglutaric acid <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion + alpha-Ketoglutarate R01513