2.0 2012-05-31 13:51:17 -0600 2015-06-03 15:54:04 -0600 ECMDB01376 M2MDB000363 2-Keto-3-deoxy-6-phosphogluconic acid 2-Keto-3-deoxy-6-phosphogluconic acid is a substrate for Fructose-bisphosphate aldolase A. 2-Dehydro-3-deoxy-6-phospho-D-gluconate 2-Dehydro-3-deoxy-6-phospho-D-gluconic acid 2-dehydro-3-Deoxy-D-gluconate 6-phosphate 2-Dehydro-3-deoxy-D-gluconate-6-phosphate 2-dehydro-3-Deoxy-D-gluconic acid-6-phosphoric acid 2-Keto-3-deoxy-6-P-gluconate 2-Keto-3-deoxy-6-P-gluconic acid 2-Keto-3-deoxy-6-phospho-D-gluconate 2-Keto-3-deoxy-6-phospho-D-gluconic acid 2-Keto-3-deoxy-6-phospho-Gluconate 2-Keto-3-deoxy-6-phospho-Gluconic acid 2-Keto-3-deoxy-6-phosphogluconate 2-Keto-3-deoxy-6-phosphogluconic acid 2-Keto-3-deoxygluconate-6-P 2-keto-3-Deoxygluconic acid-6-P 3-deoxy-D-<i>erythro</i>-hex-2-ulosonate-6-phosphate 3-deoxy-D-<i>erythro</i>-hex-2-ulosonic acid 6-phosphate 3-Deoxy-D-erythro-hex-2-ulosonate 6-phosphate 3-Deoxy-D-erythro-hex-2-ulosonate-6-phosphate 3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate 3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphoric acid 3-Deoxy-D-erythro-hex-2-ulosonic acid-6-phosphoric acid 6-p-2-k-3-Deo-gluconate 6-p-2-k-3-Deo-gluconic acid 6-Phospho-2-dehydro-3-deoxy-D-gluconate 6-Phospho-2-dehydro-3-deoxy-D-gluconic acid 6-Phospho-2-dehydro-3-deoxygluconate 6-Phospho-2-dehydro-3-deoxygluconic acid 6-Phospho-2-keto-3-deoxygluconate 6-Phospho-2-keto-3-deoxygluconic acid KDPGlcA C6H11O9P 258.1199 258.014068462 (4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acid kdpg intermediate 27244-54-8 O[C@H](COP(O)(O)=O)[C@@H](O)CC(=O)C(O)=O InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1 OVPRPPOVAXRCED-WVZVXSGGSA-N Solid Cytosol logp -2.36 ALOGPS logs -1.26 ALOGPS solubility 1.43e+01 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 1.48 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acid ChemAxon average_mass 258.1199 ChemAxon mono_mass 258.014068462 ChemAxon smiles O[C@H](COP(O)(O)=O)[C@@H](O)CC(=O)C(O)=O ChemAxon formula C6H11O9P ChemAxon inchi InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1 ChemAxon inchikey OVPRPPOVAXRCED-WVZVXSGGSA-N ChemAxon polar_surface_area 161.59 ChemAxon refractivity 47.19 ChemAxon polarizability 20.17 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Arginine and proline metabolism ec00330 Pentose and glucuronate interconversions ec00040 Glyoxylate and dicarboxylate metabolism ec00630 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 hexuronide and hexuronate degradation E. coli can use β-D-glucuronosides, D-glucuronate and D-fructuronate as an only sources of carbon for growth. β-D-glucuronosides are detoxification products that are excreted into the mammalian gut in the bile. They enter E.coli through an outer membrane protein called gusC. Once in the periplasmic space it is transported through a hydrogen symporter into the cytoplasm. Once inside the cytoplasm, the initial step in the degradation of β-glucuronides is hydrolysis by β-D-glucuronidase to yield D-glucuronate. This is then isomerized to D-fructuronate by D-glucuronate isomerase. D-fructuronate then undergoes an NADH-dependent reduction to D-mannonate by D-mannonate oxidoreductase. D-mannonate dehydratase subsequently catalyzes dehydration to yield 2-dehydro-3-deoxy-D-gluconate. At this point, a common enzyme, 2-keto-3-deoxygluconokinase, phosphorylates 2-dehydro-3-deoxy-D-gluconate to yield 2-dehydro-3-deoxy-D-gluconate-6-phosphate.This product is then process by KHG/KDPG aldolase which in turn produces D-Glyceraldehyde 3-phosphate and Pyruvic Acid which then go into their respective sub pathways: glycolysis and pyruvate dehydrogenase The pathway can also start from 3 other points: a hydrogen ion symporter (gluconate/fructuronate transporter GntP) of D-fructuronate, a hydrogen ion symporter (Hexuronate transporter) of aldehydo-D-galacturonate that spontaneously turns into D-tagaturonate and then undergoes an NADH-dependent reduction to D-altronate through an altronate oxidoreductase. D-altronate undergoes dehydration to yield 2-dehydro-3-deoxy-D-gluconate, the third and last point where the reaction can start from a hydrogen symporter of a 2-dehydro-3-deoy-D-gluconate. PW000834 Metabolic ketogluconate metabolism PW002003 Metabolic Entner-Doudoroff pathway I ENTNER-DOUDOROFF-PWY β-D-glucuronide and D-glucuronate degradation GLUCUROCAT-PWY D-galacturonate degradation I GALACTUROCAT-PWY Specdb::CMs 25704 Specdb::CMs 38044 Specdb::CMs 160207 Specdb::NmrOneD 87972 Specdb::NmrOneD 87973 Specdb::NmrOneD 87974 Specdb::NmrOneD 87975 Specdb::NmrOneD 87976 Specdb::NmrOneD 87977 Specdb::NmrOneD 87978 Specdb::NmrOneD 87979 Specdb::NmrOneD 87980 Specdb::NmrOneD 87981 Specdb::NmrOneD 87982 Specdb::NmrOneD 87983 Specdb::NmrOneD 87984 Specdb::NmrOneD 87985 Specdb::NmrOneD 87986 Specdb::NmrOneD 87987 Specdb::NmrOneD 87988 Specdb::NmrOneD 87989 Specdb::NmrOneD 87990 Specdb::NmrOneD 87991 Specdb::MsMs 25796 Specdb::MsMs 25797 Specdb::MsMs 25798 Specdb::MsMs 32354 Specdb::MsMs 32355 Specdb::MsMs 32356 Specdb::MsMs 2818422 Specdb::MsMs 2818423 Specdb::MsMs 2818424 Specdb::MsMs 2887837 Specdb::MsMs 2887838 Specdb::MsMs 2887839 HMDB01376 3080745 2338483 C04442 15925 2-KETO-3-DEOXY-6-P-GLUCONATE 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 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 KHG/KDPG aldolase P0A955 ALKH_ECOLI eda http://ecmdb.ca/proteins/P0A955.xml Phosphogluconate dehydratase P0ADF6 EDD_ECOLI edd http://ecmdb.ca/proteins/P0ADF6.xml 2-dehydro-3-deoxygluconokinase P37647 KDGK_ECOLI kdgK http://ecmdb.ca/proteins/P37647.xml 2-Keto-3-deoxy-6-phosphogluconic acid <> D-Glyceraldehyde 3-phosphate + Pyruvic acid R05605 KDPGALDOL-RXN 6-Phosphogluconic acid <> 2-Keto-3-deoxy-6-phosphogluconic acid + Water R02036 PGLUCONDEHYDRAT-RXN 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate <> 2-Keto-3-deoxy-6-phosphogluconic acid + ADP + Hydrogen ion R01541 DEOXYGLUCONOKIN-RXN Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid <> ADP + 2-Keto-3-deoxy-6-phosphogluconic acid R01541 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + ADP DEOXYGLUCONOKIN-RXN 2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid KDPGALDOL-RXN 6-Phosphogluconic acid > 2-Keto-3-deoxy-6-phosphogluconic acid + Water R02036 PGLUCONDEHYDRAT-RXN Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > ADP + 2-Keto-3-deoxy-6-phosphogluconic acid 2-Dehydro-3-deoxy-D-galactonate + Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + Adenosine diphosphate + ADP PW_R003064 2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid + D-Glyceraldehyde 3-phosphate PW_R003065 gluconate 6-phosphate > Water + 2-Keto-3-deoxy-6-phosphogluconic acid PW_R005700 6 6-Phosphogluconic acid <>2 2-Keto-3-deoxy-6-phosphogluconic acid + Water