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Record Information
Version	2.0
Creation Date	2012-05-31 13:49:48 -0600
Update Date	2015-09-13 12:56:10 -0600
Secondary Accession Numbers	ECMDB01316
Identification
Name:	6-Phosphogluconic acid
Description	6-Phosphogluconic acid is an intermediate in the Pentose phosphate pathway (KEGG)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa8720e2c> Close
Synonyms:	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
Chemical Formula:	C6H13O10P
Weight:	Average: 276.1352 Monoisotopic: 276.024633148
InChI Key:	BIRSGZKFKXLSJQ-SQOUGZDYSA-N
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
CAS number:	921-62-0
IUPAC Name:	(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid
Traditional IUPAC Name:	6-phosphogluconic acid
SMILES:	O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Monosaccharide phosphates
Alternative Parents	Hexoses Medium-chain hydroxy acids and derivatives Medium-chain fatty acids Sugar acids and derivatives Monoalkyl phosphates Hydroxy fatty acids Beta hydroxy acids and derivatives Alpha hydroxy acids and derivatives Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Gluconic_acid Hexose monosaccharide Monosaccharide phosphate Medium-chain hydroxy acid Medium-chain fatty acid Monoalkyl phosphate Beta-hydroxy acid Hydroxy fatty acid Alkyl phosphate Fatty acid Alpha-hydroxy acid Phosphoric acid ester Organic phosphoric acid derivative Fatty acyl Hydroxy acid Secondary alcohol Polyol Monocarboxylic acid or derivatives Carboxylic acid derivative Carboxylic acid Carbonyl group Alcohol Organic oxide Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	gluconic acid phosphate (CHEBI:48928 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 20.7 g/L ALOGPS logP -2.3 ALOGPS logP -3.5 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.49 ChemAxon pKa (Strongest Basic) -3.5 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 184.98 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 49.14 m³·mol⁻¹ ChemAxon Polarizability 21.6 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Adenosine triphosphate + Gluconic acid <> 6-Phosphogluconic acid + ADP + Hydrogen ion 6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acid + Hydrogen ion 6-Phosphogluconic acid <> 2-Keto-3-deoxy-6-phosphogluconic acid + Water 6-Phosphogluconic acid + NADP <> Carbon dioxide + NADPH + D-Ribulose 5-phosphate + Hydrogen ion 6-Phosphogluconic acid + NADP <> D-Ribulose 5-phosphate + Carbon dioxide + NADPH + Hydrogen ion Adenosine triphosphate + Gluconic acid <> ADP + 6-Phosphogluconic acid 6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acid NAD(P)<sup>+</sup> + 6-Phosphogluconic acid > NAD(P)H + D-Ribulose 5-phosphate + Carbon dioxide 6-Phosphonoglucono-D-lactone + Water > Hydrogen ion + 6-Phosphogluconic acid Adenosine triphosphate + Gluconic acid > Hydrogen ion + ADP + 6-Phosphogluconic acid 6-Phosphogluconic acid > 2-Keto-3-deoxy-6-phosphogluconic acid + Water 6-Phosphogluconic acid + Water > Gluconic acid + Phosphate 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 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
SMPDB Pathways:	Glutathione metabolism PW000833 Pentose Phosphate PW000893
KEGG Pathways:	Glutathione metabolism ec00480 Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120 Pentose phosphate pathway ec00030
EcoCyc Pathways:	D-gluconate degradation GLUCONSUPER-PWY Entner-Doudoroff pathway I ENTNER-DOUDOROFF-PWY L-idonate degradation IDNCAT-PWY pentose phosphate pathway (oxidative branch) OXIDATIVEPENT-PWY superpathway of glycolysis and Entner-Doudoroff GLYCOLYSIS-E-D
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 310± 0 uM W3110 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 Mid Log Phase Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h 37 oC 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. 450± 32 uM K12 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 Stationary Phase, glucose limited Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h 37 oC PMID: 11488613 380± 70 uM BW25113 M9 Minimal Media, 4 g/L Glucose Mid-Log Phase Bioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h 37 oC PMID: 15158257 3770± 0 uM K12 NCM3722 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 Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 400± 0 uM K12 NCM3722 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 Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 193± 0 uM K12 NCM3722 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 Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (5 TMS) splash10-0uxu-0933000000-d0c837bb667abbae2ce0 View in MoNA GC-MS GC-MS Spectrum - GC-MS (7 TMS) splash10-00ks-1978000000-c7702d284ad9f06bb5c0 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0uxu-0933000000-d0c837bb667abbae2ce0 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-00ks-1978000000-c7702d284ad9f06bb5c0 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0a4j-9430000000-e4198ba354325082e116 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive splash10-00dl-7192047000-e8fa0bd25a22fa6fd28b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) splash10-00dj-5090000000-a1b0f01abec0e4fb22c5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) splash10-002b-9000000000-780e6dc35ed33dde8b62 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) splash10-004i-9000000000-df8e5979c41c127eff41 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-00b9-0495110000-a9d468f24ea04c2dd0d2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-0002-9100000000-25ef4bb1cdb69b6418ce View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-0a4j-5090000000-6db5e52f38f29e35f42a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-004i-0090000000-b6ed9e59bd4492f4b5ce View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-004i-0190000000-50702b7e8f4b7289d218 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-004j-9260000000-e356e1c75aa70d0065f9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-002b-9100000000-5be967e173f74d688dc2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-004j-9000000000-1c5eda88c214ef66d7b6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-004i-9000000000-e1b81e634eb90448b9cd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-0090000000-50702b7e8f4b7289d218 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004j-9260000000-20df41bde9cbb406f532 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-002b-9100000000-56434d8c214a22e12603 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004j-9000000000-1c5eda88c214ef66d7b6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-9000000000-e1b81e634eb90448b9cd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT , negative splash10-0002-9100000000-25ef4bb1cdb69b6418ce View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT , negative splash10-0a4j-5090000000-6db5e52f38f29e35f42a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-056r-2590000000-53a3a79c2cc73c243e4e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a6v-7920000000-e9b87a1b1cd046187a03 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a6r-9400000000-299a98a9b8ecad68997d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9830000000-f784c955d104bea3213f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9300000000-bffd36c521b6f41716d9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-d27f7e55395c8a6e1547 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Ahmed N, Weidemann MJ: Purine metabolism in promyelocytic HL60 and dimethylsulphoxide-differentiated HL60 cells. Leuk Res. 1994 Jun;18(6):441-51. Pubmed: 8207962 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. Pubmed: 19561621 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. Pubmed: 11488613 Chen SH, Karp LE, Scott CR, Chen W: Use of genetic markers to certify fetal origin of cultured amniotic fluid cells. Hum Genet. 1981;57(3):323-4. Pubmed: 6454643 Harada S: Isoelectrofocusing in acetate membrane: the method and application. Clin Chim Acta. 1975 Sep 16;63(3):275-83. Pubmed: 240520 Harmon CS, Phizackerley PJ: Glycogen metabolism in psoriatic epidermis and in regenerating epidermis. Clin Sci (Lond). 1984 Sep;67(3):291-8. Pubmed: 6432401 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. Pubmed: 22080510 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. Pubmed: 21097882 Moghetti P, Bonora E, Cigolini M, Querena M, Cacciatori V, Muggeo M: Enzymatic activities related to intermediary metabolism of glucose in circulating mononuclear cells from obese humans: relationship to enzyme activity in adipose tissue. Enzyme. 1990;43(1):26-32. Pubmed: 2141817 Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454 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. 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. Pubmed: 15158257 Schwerd W, Fehrer HD: [The detection of inherited enzyme polymorphism in semen (author's transl)] Z Rechtsmed. 1979 Jul 17;83(2):129-38. Pubmed: 494813 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Swierczynski J, Goyke E, Wach L, Pankiewicz A, Kochan Z, Adamonis W, Sledzinski Z, Aleksandrowicz Z: Comparative study of the lipogenic potential of human and rat adipose tissue. Metabolism. 2000 May;49(5):594-9. Pubmed: 10831168 Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. Epub 2005 Jan 23. Pubmed: 16055050 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. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 16863 HMDB ID HMDB01316 Pubchem Compound ID 91493 Kegg ID C00345 ChemSpider ID 82615 Wikipedia 6-phosphogluconate BioCyc ID CPD-2961 EcoCyc ID CPD-2961 Ligand Expo 6PG

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