2.0 2012-05-31 14:27:35 -0600 2015-06-03 17:19:19 -0600 ECMDB20102 M2MDB000950 5-Dehydro-4-deoxy-D-glucarate 5-dehydro-4-deoxy-D-glucarate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. KDG is invovled in D-glucarate metabolism. Crystals of GlucD have been obtained into which the substrate D-glucarate and two competitive inhibitors, 4-deoxy-D-glucarate and xylarohydroxamate, could be diffused; D-glucarate is converted to the dehydration product, 5-keto-4-deoxy-D-glucarate (KDG). (PMID 10769114) 2,3-Dihydroxy-5-oxo-hexanedioate 2,3-Dihydroxy-5-oxo-hexanedioic acid 3-deoxy-(L)-threo-2-hexulosarate 3-Deoxy-(L)-threo-2-hexulosarate 3-Deoxy-(L)-threo-2-hexulosaric acid 3-deoxy-L-threo-hex-2-ulosarate 3-Deoxy-L-threo-hex-2-ulosarate 3-Deoxy-L-threo-hex-2-ulosaric acid 5-Dehydro-4-deoxy-D-glucarate 5-Dehydro-4-deoxy-D-glucaric acid 5-KDG 5-Keto-4-deoxy-D-glucarate 5-Keto-4-deoxy-D-glucaric acid GLR KDG KGR C6H8O7 192.1235 192.02700261 (2R,3S)-2,3-dihydroxy-5-oxohexanedioic acid 5-dehydro-4-deoxy-D-glucarate [H][C@](O)(CC(=O)C(O)=O)[C@@]([H])(O)C(O)=O InChI=1S/C6H8O7/c7-2(4(9)6(12)13)1-3(8)5(10)11/h2,4,7,9H,1H2,(H,10,11)(H,12,13)/t2-,4+/m0/s1 QUURPCHWPQNNGL-ZAFYKAAXSA-N Cytosol logp -1.23 ALOGPS logs -0.56 ALOGPS solubility 5.27e+01 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 2.5 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (2R,3S)-2,3-dihydroxy-5-oxohexanedioic acid ChemAxon average_mass 192.1235 ChemAxon mono_mass 192.02700261 ChemAxon smiles [H][C@](O)(CC(=O)C(O)=O)[C@@]([H])(O)C(O)=O ChemAxon formula C6H8O7 ChemAxon inchi InChI=1S/C6H8O7/c7-2(4(9)6(12)13)1-3(8)5(10)11/h2,4,7,9H,1H2,(H,10,11)(H,12,13)/t2-,4+/m0/s1 ChemAxon inchikey QUURPCHWPQNNGL-ZAFYKAAXSA-N ChemAxon polar_surface_area 132.13 ChemAxon refractivity 36.18 ChemAxon polarizability 15.51 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Ascorbate and aldarate metabolism ec00053 Metabolic pathways eco01100 D-galactarate degradation I GALACTARDEG-PWY D-glucarate degradation I GLUCARDEG-PWY Specdb::CMs 1084461 Specdb::NmrOneD 258048 Specdb::NmrOneD 258049 Specdb::NmrOneD 258050 Specdb::NmrOneD 258051 Specdb::NmrOneD 258052 Specdb::NmrOneD 258053 Specdb::NmrOneD 258054 Specdb::NmrOneD 258055 Specdb::NmrOneD 258056 Specdb::NmrOneD 258057 Specdb::NmrOneD 258058 Specdb::NmrOneD 258059 Specdb::NmrOneD 258060 Specdb::NmrOneD 258061 Specdb::NmrOneD 258062 Specdb::NmrOneD 258063 Specdb::NmrOneD 258064 Specdb::NmrOneD 258065 Specdb::NmrOneD 258066 Specdb::NmrOneD 258067 Specdb::MsMs 26429 Specdb::MsMs 26430 Specdb::MsMs 26431 Specdb::MsMs 32987 Specdb::MsMs 32988 Specdb::MsMs 32989 439290 388423 C00679 42819 5-KETO-4-DEOXY-D-GLUCARATE KGR 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 Glucarate dehydratase P0AES2 GUDH_ECOLI gudD http://ecmdb.ca/proteins/P0AES2.xml 5-keto-4-deoxy-D-glucarate aldolase P23522 GARL_ECOLI garL http://ecmdb.ca/proteins/P23522.xml D-galactarate dehydratase P39829 GARD_ECOLI garD http://ecmdb.ca/proteins/P39829.xml Glucarate dehydratase-related protein Q46915 GUDX_ECOLI gudX http://ecmdb.ca/proteins/Q46915.xml Glucaric acid > 5-Dehydro-4-deoxy-D-glucarate + Water GLUCARDEHYDRA-RXN 5-Dehydro-4-deoxy-D-glucarate > Tartronate semialdehyde + Pyruvic acid R02754 KDGALDOL-RXN Galactaric acid > 5-Dehydro-4-deoxy-D-glucarate + Water GALACTARDEHYDRA-RXN D-Glucarate + Glucaric acid <> 5-Dehydro-4-deoxy-D-glucarate + Water R02752 5-Dehydro-4-deoxy-D-glucarate <> Pyruvic acid + Tartronate semialdehyde R02754 D-Galactarate + Galactaric acid <> 5-Dehydro-4-deoxy-D-glucarate + Water R05608 D-glucarate > 5-Dehydro-4-deoxy-D-glucarate + Water