2.0 2012-05-31 13:49:48 -0600 2015-09-13 12:56:10 -0600 ECMDB01316 M2MDB000336 6-Phosphogluconic acid 6-Phosphogluconic acid is an intermediate in the Pentose phosphate pathway (KEGG) 6-O-Phosphono-D-gluconate 6-O-Phosphono-D-gluconic acid 6-p Gluconate 6-p Gluconic acid 6-p-Gluconate 6-p-Gluconic acid 6-PG 6-Phospho gluconate 6-Phospho gluconic acid 6-Phospho-D-gluconate 6-Phospho-D-gluconic acid 6-Phosphogluconate 6-Phosphogluconic acid D-Gluconate 6-(dihydrogen phosphate) D-Gluconate 6-phosphate D-Gluconic acid 6-(dihydrogen phosphate) D-Gluconic acid 6-(dihydrogen phosphoric acid) D-Gluconic acid 6-phosphate D-Gluconic acid 6-phosphoric acid Gluconate-6-phosphate Gluconic acid-6-phosphate Gluconic acid-6-phosphoric acid C6H13O10P 276.1352 276.024633148 (2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid 6-phosphogluconic acid 921-62-0 O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O InChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1 BIRSGZKFKXLSJQ-SQOUGZDYSA-N Solid Cytosol logp -2.27 ALOGPS logs -1.12 ALOGPS solubility 2.07e+01 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid ChemAxon average_mass 276.1352 ChemAxon mono_mass 276.024633148 ChemAxon smiles O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O ChemAxon formula C6H13O10P ChemAxon inchi InChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1 ChemAxon inchikey BIRSGZKFKXLSJQ-SQOUGZDYSA-N ChemAxon polar_surface_area 184.98 ChemAxon refractivity 49.14 ChemAxon polarizability 21.6 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Glutathione metabolism The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. PW000833 ec00480 Metabolic Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Pentose Phosphate PW000893 Metabolic superpathway of glycolysis and Entner-Doudoroff GLYCOLYSIS-E-D pentose phosphate pathway (oxidative branch) OXIDATIVEPENT-PWY Entner-Doudoroff pathway I ENTNER-DOUDOROFF-PWY D-gluconate degradation GLUCONSUPER-PWY L-idonate degradation IDNCAT-PWY Specdb::CMs 1921 Specdb::CMs 1967 Specdb::CMs 2360 Specdb::CMs 31309 Specdb::CMs 31310 Specdb::CMs 38020 Specdb::CMs 134970 Specdb::CMs 142704 Specdb::NmrOneD 1681 Specdb::NmrOneD 4797 Specdb::NmrOneD 4798 Specdb::NmrOneD 87732 Specdb::NmrOneD 87733 Specdb::NmrOneD 87734 Specdb::NmrOneD 87735 Specdb::NmrOneD 87736 Specdb::NmrOneD 87737 Specdb::NmrOneD 87738 Specdb::NmrOneD 87739 Specdb::NmrOneD 87740 Specdb::NmrOneD 87741 Specdb::NmrOneD 87742 Specdb::NmrOneD 87743 Specdb::NmrOneD 87744 Specdb::NmrOneD 87745 Specdb::NmrOneD 87746 Specdb::NmrOneD 87747 Specdb::NmrOneD 87748 Specdb::NmrOneD 87749 Specdb::NmrOneD 87750 Specdb::NmrOneD 87751 Specdb::MsMs 1516 Specdb::MsMs 1517 Specdb::MsMs 1518 Specdb::MsMs 5186 Specdb::MsMs 5187 Specdb::MsMs 5188 Specdb::MsMs 5189 Specdb::MsMs 5190 Specdb::MsMs 5191 Specdb::MsMs 5192 Specdb::MsMs 5193 Specdb::MsMs 5194 Specdb::MsMs 438259 Specdb::MsMs 438260 Specdb::MsMs 438261 Specdb::MsMs 438262 Specdb::MsMs 438263 Specdb::MsMs 438875 Specdb::MsMs 438876 Specdb::MsMs 438877 Specdb::MsMs 2252862 Specdb::MsMs 2253596 Specdb::MsMs 2254975 Specdb::MsMs 2255622 Specdb::MsMs 1473426 Specdb::NmrTwoD 1064 Specdb::NmrTwoD 1622 HMDB01316 91493 82615 C00345 16863 CPD-2961 6PG 6-phosphogluconate Keseler, I. 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Metabolism. 2000 May;49(5):594-9. 10831168 http://hmdb.ca/system/metabolites/msds/000/001/178/original/HMDB01316.pdf?1358461551 6-phosphogluconate dehydrogenase, decarboxylating P00350 6PGD_ECOLI gnd http://ecmdb.ca/proteins/P00350.xml Phosphogluconate dehydratase P0ADF6 EDD_ECOLI edd http://ecmdb.ca/proteins/P0ADF6.xml Thermosensitive gluconokinase P39208 IDNK_ECOLI idnK http://ecmdb.ca/proteins/P39208.xml Thermoresistant gluconokinase P46859 GNTK_ECOLI gntK http://ecmdb.ca/proteins/P46859.xml 6-phosphogluconolactonase P52697 6PGL_ECOLI pgl http://ecmdb.ca/proteins/P52697.xml Adenosine triphosphate + Gluconic acid <> 6-Phosphogluconic acid + ADP + Hydrogen ion R01737 GLUCONOKIN-RXN 6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acid + Hydrogen ion R02035 6PGLUCONOLACT-RXN 6-Phosphogluconic acid <> 2-Keto-3-deoxy-6-phosphogluconic acid + Water R02036 PGLUCONDEHYDRAT-RXN 6-Phosphogluconic acid + NADP <> Carbon dioxide + NADPH + D-Ribulose 5-phosphate + Hydrogen ion R01528 6-Phosphogluconic acid + NADP <> D-Ribulose 5-phosphate + Carbon dioxide + NADPH + Hydrogen ion R01528 Adenosine triphosphate + Gluconic acid <> ADP + 6-Phosphogluconic acid R01737 GLUCONOKIN-RXN 6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acid R02035 NAD(P)⁺ + 6-Phosphogluconic acid > NAD(P)H + D-Ribulose 5-phosphate + Carbon dioxide 6PGLUCONDEHYDROG-RXN 6-Phosphonoglucono-D-lactone + Water > Hydrogen ion + 6-Phosphogluconic acid 6PGLUCONOLACT-RXN Adenosine triphosphate + Gluconic acid > Hydrogen ion + ADP + 6-Phosphogluconic acid GLUCONOKIN-RXN 6-Phosphogluconic acid > 2-Keto-3-deoxy-6-phosphogluconic acid + Water R02036 PGLUCONDEHYDRAT-RXN 6-Phosphogluconic acid + Water > Gluconic acid + Phosphate RXN0-5185 6-Phosphogluconic acid + NADP > D-Ribulose 5-phosphate + Carbon dioxide + NADPH 6-Phosphonoglucono-D-lactone + Water > 6-Phosphogluconic acid Adenosine triphosphate + Gluconic acid > ADP + 6-Phosphogluconic acid 6-Phosphogluconic acid + NADP > D-Ribulose 5-phosphate + Carbon dioxide + NADPH + NADPH PW_R003340 6 6-Phosphonoglucono-D-lactone + Water <>6 6-Phosphogluconic acid + Hydrogen ion 6 6-Phosphonoglucono-D-lactone + Water <>6 6-Phosphogluconic acid 6 6-Phosphogluconic acid <>2 2-Keto-3-deoxy-6-phosphogluconic acid + Water 6 6-Phosphonoglucono-D-lactone + Water <>6 6-Phosphogluconic acid + Hydrogen ion 4.0 g/L Na2SO4; 5.36 g/L (NH4)2SO4; 1.0 g/L NH4Cl; 7.3 g/L K2HPO4; 1.8 g/L NaH2PO4 H2O; 12.0 g/L (NH4)2-H-citrate; 4.0 mL/L MgSO4 (1 M); 6.0 mL/L trace element solution; 0.02 g/L thiamine, 20 g/L glucose Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h 309.9 uM 0.0 37 oC W3110 Mid Log Phase 1239600 0 Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530. 0.2 g/L NH4Cl, 2.0 g/L (NH4)2SO4, 3.25 g/L KH2PO4, 2.5 g/L K2HPO4, 1.5 g/L NaH2PO4, 0.5 g/L MgSO4; trace substances: 10 mg/L CaCl2, 0.5 mg/L ZnSO4, 0.25 mg/L CuCl2, 0.25 mg/L MnSO4, 0.175 mg/L CoCl2, 0.125 mg/L H3BO3, 2.5 mg/L AlCl3, 0.5 mg/L Na2MoO4, 10 Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h 450.0 uM 32.0 37 oC K12 Stationary Phase, glucose limited 1800000 128000 Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. 11488613 M9 Minimal Media, 4 g/L Glucose Bioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h 380.0 uM 70.0 37 oC BW25113 Mid-Log Phase 1520000 280000 Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23. 15158257 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 3770.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 15080000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 400.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 1600000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 193.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 772000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621