2.02012-05-31 13:49:48 -06002015-09-13 12:56:10 -0600ECMDB01316M2MDB0003366-Phosphogluconic acid6-Phosphogluconic acid is an intermediate in the Pentose phosphate pathway (KEGG)6-O-Phosphono-D-gluconate6-O-Phosphono-D-gluconic acid6-p Gluconate6-p Gluconic acid6-p-Gluconate6-p-Gluconic acid6-PG6-Phospho gluconate6-Phospho gluconic acid6-Phospho-D-gluconate6-Phospho-D-gluconic acid6-Phosphogluconate6-Phosphogluconic acidD-Gluconate 6-(dihydrogen phosphate)D-Gluconate 6-phosphateD-Gluconic acid 6-(dihydrogen phosphate)D-Gluconic acid 6-(dihydrogen phosphoric acid)D-Gluconic acid 6-phosphateD-Gluconic acid 6-phosphoric acidGluconate-6-phosphateGluconic acid-6-phosphateGluconic acid-6-phosphoric acidC6H13O10P276.1352276.024633148(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid6-phosphogluconic acid921-62-0O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=OInChI=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/s1BIRSGZKFKXLSJQ-SQOUGZDYSA-NSolidCytosollogp-2.27logs-1.12solubility2.07e+01 g/llogp-3.5pka_strongest_acidic1.49pka_strongest_basic-3.5iupac(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acidaverage_mass276.1352mono_mass276.024633148smilesO[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=OformulaC6H13O10PinchiInChI=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/s1inchikeyBIRSGZKFKXLSJQ-SQOUGZDYSA-Npolar_surface_area184.98refractivity49.14polarizability21.6rotatable_bond_count7acceptor_count9donor_count7physiological_charge-3formal_charge0Pentose phosphate pathwayec00030Glutathione metabolismThe 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.
PW000833ec00480MetabolicMicrobial metabolism in diverse environmentsec01120Metabolic pathwayseco01100Pentose PhosphatePW000893Metabolicsuperpathway of glycolysis and Entner-DoudoroffGLYCOLYSIS-E-Dpentose phosphate pathway (oxidative branch)OXIDATIVEPENT-PWYEntner-Doudoroff pathway IENTNER-DOUDOROFF-PWYD-gluconate degradationGLUCONSUPER-PWYL-idonate degradationIDNCAT-PWYSpecdb::CMs1921Specdb::CMs1967Specdb::CMs2360Specdb::CMs31309Specdb::CMs31310Specdb::CMs38020Specdb::CMs134970Specdb::CMs142704Specdb::NmrOneD1681Specdb::NmrOneD4797Specdb::NmrOneD4798Specdb::NmrOneD87732Specdb::NmrOneD87733Specdb::NmrOneD87734Specdb::NmrOneD87735Specdb::NmrOneD87736Specdb::NmrOneD87737Specdb::NmrOneD87738Specdb::NmrOneD87739Specdb::NmrOneD87740Specdb::NmrOneD87741Specdb::NmrOneD87742Specdb::NmrOneD87743Specdb::NmrOneD87744Specdb::NmrOneD87745Specdb::NmrOneD87746Specdb::NmrOneD87747Specdb::NmrOneD87748Specdb::NmrOneD87749Specdb::NmrOneD87750Specdb::NmrOneD87751Specdb::MsMs1516Specdb::MsMs1517Specdb::MsMs1518Specdb::MsMs5186Specdb::MsMs5187Specdb::MsMs5188Specdb::MsMs5189Specdb::MsMs5190Specdb::MsMs5191Specdb::MsMs5192Specdb::MsMs5193Specdb::MsMs5194Specdb::MsMs438259Specdb::MsMs438260Specdb::MsMs438261Specdb::MsMs438262Specdb::MsMs438263Specdb::MsMs438875Specdb::MsMs438876Specdb::MsMs438877Specdb::MsMs2252862Specdb::MsMs2253596Specdb::MsMs2254975Specdb::MsMs2255622Specdb::MsMs1473426Specdb::NmrTwoD1064Specdb::NmrTwoD1622HMDB013169149382615C0034516863CPD-29616PG6-phosphogluconateKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Winder, 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 80:2939-2948.18331064Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). 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Metabolism. 2000 May;49(5):594-9.10831168http://hmdb.ca/system/metabolites/msds/000/001/178/original/HMDB01316.pdf?13584615516-phosphogluconate dehydrogenase, decarboxylatingP003506PGD_ECOLIgndhttp://ecmdb.ca/proteins/P00350.xmlPhosphogluconate dehydrataseP0ADF6EDD_ECOLIeddhttp://ecmdb.ca/proteins/P0ADF6.xmlThermosensitive gluconokinaseP39208IDNK_ECOLIidnKhttp://ecmdb.ca/proteins/P39208.xmlThermoresistant gluconokinaseP46859GNTK_ECOLIgntKhttp://ecmdb.ca/proteins/P46859.xml6-phosphogluconolactonaseP526976PGL_ECOLIpglhttp://ecmdb.ca/proteins/P52697.xmlAdenosine triphosphate + Gluconic acid <> 6-Phosphogluconic acid + ADP + Hydrogen ionR01737GLUCONOKIN-RXN6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acid + Hydrogen ionR020356PGLUCONOLACT-RXN6-Phosphogluconic acid <> 2-Keto-3-deoxy-6-phosphogluconic acid + WaterR02036PGLUCONDEHYDRAT-RXN6-Phosphogluconic acid + NADP <> Carbon dioxide + NADPH + D-Ribulose 5-phosphate + Hydrogen ionR015286-Phosphogluconic acid + NADP <> D-Ribulose 5-phosphate + Carbon dioxide + NADPH + Hydrogen ionR01528Adenosine triphosphate + Gluconic acid <> ADP + 6-Phosphogluconic acidR01737GLUCONOKIN-RXN6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acidR02035NAD(P)<sup>+</sup> + 6-Phosphogluconic acid > NAD(P)H + D-Ribulose 5-phosphate + Carbon dioxide6PGLUCONDEHYDROG-RXN6-Phosphonoglucono-D-lactone + Water > Hydrogen ion + 6-Phosphogluconic acid6PGLUCONOLACT-RXNAdenosine triphosphate + Gluconic acid > Hydrogen ion + ADP + 6-Phosphogluconic acidGLUCONOKIN-RXN6-Phosphogluconic acid > 2-Keto-3-deoxy-6-phosphogluconic acid + WaterR02036PGLUCONDEHYDRAT-RXN6-Phosphogluconic acid + Water > Gluconic acid + PhosphateRXN0-51856-Phosphogluconic acid + NADP > D-Ribulose 5-phosphate + Carbon dioxide + NADPH6-Phosphonoglucono-D-lactone + Water > 6-Phosphogluconic acidAdenosine triphosphate + Gluconic acid > ADP + 6-Phosphogluconic acid6-Phosphogluconic acid + NADP > D-Ribulose 5-phosphate + Carbon dioxide + NADPH + NADPHPW_R0033406 6-Phosphonoglucono-D-lactone + Water <>6 6-Phosphogluconic acid + Hydrogen ion6 6-Phosphonoglucono-D-lactone + Water <>6 6-Phosphogluconic acid6 6-Phosphogluconic acid <>2 2-Keto-3-deoxy-6-phosphogluconic acid + Water6 6-Phosphonoglucono-D-lactone + Water <>6 6-Phosphogluconic acid + Hydrogen ion4.0 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 glucoseBioreactor, pH controlled, aerated, dilution rate=0.125 L/h309.9uM0.037 oCW3110Mid Log Phase12396000Park, 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, 10Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h450.0uM32.037 oCK12Stationary Phase, glucose limited1800000128000Buchholz, 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 295:129-137.11488613M9 Minimal Media, 4 g/L GlucoseBioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h380.0uM70.037 oCBW25113Mid-Log Phase1520000280000Peng, 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 235:17-23.15158257Gutnick 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 glucoseShake flask and filter culture3770.0uM0.037 oCK12 NCM3722Mid-Log Phase150800000Bennett, 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 5:593-599.19561621Gutnick 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 glycerolShake flask and filter culture400.0uM0.037 oCK12 NCM3722Mid-Log Phase16000000Bennett, 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 5:593-599.19561621Gutnick 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 acetateShake flask and filter culture193.0uM0.037 oCK12 NCM3722Mid-Log Phase7720000Bennett, 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