2.0 2012-05-31 14:24:18 -0600 2015-06-03 17:19:11 -0600 ECMDB20040 M2MDB000889 2-Dehydro-3-deoxy-D-glucarate 2-dehydro-3-deoxy-D-glucarate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. It is a substrate for 2-dehydro-3-deoxyglucarate aldolase (EC 4.1.2.20) which is an enzyme that catalyzes the chemical reaction: 2-dehydro-3-deoxy-D-glucarate = pyruvate + tartronate semialdehyde 2-Dehydro-3-deoxy-D-glucarate 2-Dehydro-3-deoxy-D-glucaric acid 2-Keto-3-deoxy-D-glucarate 2-Keto-3-deoxy-D-glucaric acid 2-Keto-3-deoxy-glucarate 2-Keto-3-deoxy-glucaric acid 3-Deoxy-D-erythro-hex-2-ulosarate 3-Deoxy-D-erythro-hex-2-ulosaric acid KGR C6H8O7 192.1235 192.02700261 (2S,3S)-2,3-dihydroxy-5-oxohexanedioic acid 2-dehydro-3-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-OKKQSCSOSA-N Cytoplasm Periplasm 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 (2S,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-OKKQSCSOSA-N ChemAxon polar_surface_area 132.13 ChemAxon refractivity 36.18 ChemAxon polarizability 15.49 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 superpathway of D-glucarate and D-galactarate degradation Galactarate is a naturally occurring dicarboxylic acid analog of D-galactose. E. coli can use both diacid sugars galactarate and D-glucarate as the sole source of carbon for growth. The initial step in the degradation of galactarate is its dehydration to 5-dehydro-4-deoxy-D-glucarate(2--) by galactarate dehydratase. Glucaric acid can also be dehydrated by a glucarate dehydratase resulting in water and 5-dehydro-4-deoxy-D-glucarate(2--). The 5-dehydro-4-deoxy-D-glucarate(2--) is then metabolized by a alpha-dehydro-beta-deoxy-D-glucarate aldolase resulting in pyruvic acid and a tartonate semialdehyde. Pyruvic acid interacts with coenzyme A through a NAD driven Pyruvate dehydrogenase complex resulting in a carbon dioxide, an NADH and an acetyl-CoA. The tartronate semialdehyde interacts with a hydrogen ion through a NADPH driven tartronate semialdehyde reductase resulting in a NADP and a glyceric acid. The glyceric acid is phosphorylated by an ATP-driven glycerate kinase 2 resulting in an ADP, a hydrogen ion and a 2-phosphoglyceric acid. The latter compound is dehydrated by an enolase resulting in the release of water and a phosphoenolpyruvic acid. The phosphoenolpyruvic acid interacts with a hydrogen ion through an ADP driven pyruvate kinase resulting in an ATP and a pyruvic acid. The pyruvic acid then interacts with water and an ATP through a phosphoenolpyruvate synthetase resulting in the release of a hydrogen ion, a phosphate, an AMP and a Phosphoenolpyruvic acid. PW000795 Metabolic Specdb::CMs 1084208 Specdb::NmrOneD 276658 Specdb::NmrOneD 276659 Specdb::NmrOneD 276660 Specdb::NmrOneD 276661 Specdb::NmrOneD 276662 Specdb::NmrOneD 276663 Specdb::NmrOneD 276664 Specdb::NmrOneD 276665 Specdb::NmrOneD 276666 Specdb::NmrOneD 276667 Specdb::NmrOneD 276668 Specdb::NmrOneD 276669 Specdb::NmrOneD 276670 Specdb::NmrOneD 276671 Specdb::NmrOneD 276672 Specdb::NmrOneD 276673 Specdb::NmrOneD 276674 Specdb::NmrOneD 276675 Specdb::NmrOneD 276676 Specdb::NmrOneD 276677 Specdb::MsMs 25391 Specdb::MsMs 25392 Specdb::MsMs 25393 Specdb::MsMs 31949 Specdb::MsMs 31950 Specdb::MsMs 31951 440165 389156 C03921 17305 2-KETO-3-DEOXY-D-GLUCARATE 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 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 Tartronate semialdehyde + Pyruvic acid <> 2-Dehydro-3-deoxy-D-glucarate R03277 D-Glucarate <> 2-Dehydro-3-deoxy-D-glucarate + Water R08056 2-Dehydro-3-deoxy-D-glucarate > Pyruvic acid + Tartronate semialdehyde Glucaric acid > Water + 2-Dehydro-3-deoxy-D-glucarate PW_R005867