Record Information
Version2.0
Creation Date2012-05-31 13:49:48 -0600
Update Date2015-09-13 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
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentMonosaccharide phosphates
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility20.7 mg/mLALOGPS
logP-2.3ALOGPS
logP-3.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area184.98 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.14 m3·mol-1ChemAxon
Polarizability21.6 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
6-Phosphogluconic acid <> 2-Keto-3-deoxy-6-phosphogluconic acid + Water
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
6-Phosphogluconic acid > 2-Keto-3-deoxy-6-phosphogluconic acid + Water
Adenosine triphosphate + Gluconic acid > ADP + 6-Phosphogluconic acid
Adenosine triphosphate + Gluconic acid > ADP + 6-Phosphogluconic acid
6-Phosphogluconic acid + NADP > D-Ribulose 5-phosphate + Carbon dioxide + NADPH + NADPH
6-Phosphonoglucono-D-lactone + Water > 6-Phosphogluconic acid + Hydrogen ion
SMPDB Pathways:
Glutathione metabolismPW000833 Pw000833Pw000833 greyscalePw000833 simple
Pentose PhosphatePW000893 Pw000893Pw000893 greyscalePw000893 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
310± 0 uMW31104.0 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 glucoseMid Log PhaseBioreactor, pH controlled, aerated, dilution rate=0.125 L/h37 oCPark, 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 uMK120.2 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, 10Stationary Phase, glucose limitedBioreactor, pH controlled, aerated, dilution rate=0.125 L/h37 oCPMID: 11488613
380± 70 uMBW25113M9 Minimal Media, 4 g/L GlucoseMid-Log PhaseBioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h37 oCPMID: 15158257
3770± 0 uMK12 NCM3722Gutnick 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 glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
400± 0 uMK12 NCM3722Gutnick 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 glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
193± 0 uMK12 NCM3722Gutnick 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 acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0uxu-0933000000-d0c837bb667abbae2ce0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-00ks-1978000000-c7702d284ad9f06bb5c0View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-MSsplash10-0uxu-0933000000-d0c837bb667abbae2ce0View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00ks-1978000000-c7702d284ad9f06bb5c0View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dj-5090000000-a1b0f01abec0e4fb22c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d218View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d218View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f532View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e12603View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e1b81e634eb90448b9cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2590000000-53a3a79c2cc73c243e4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6v-7920000000-e9b87a1b1cd046187a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-299a98a9b8ecad68997dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9830000000-f784c955d104bea3213fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-bffd36c521b6f41716d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d27f7e55395c8a6e1547View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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)
External Links:
ResourceLink
CHEBI ID16863
HMDB IDHMDB01316
Pubchem Compound ID91493
Kegg IDC00345
ChemSpider ID82615
Wikipedia6-phosphogluconate
BioCyc IDCPD-2961
EcoCyc IDCPD-2961
Ligand Expo6PG

Enzymes

General function:
Involved in oxidation-reduction process
Specific function:
Catalyzes the oxidative decarboxylation of 6- phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH
Gene Name:
gnd
Uniprot ID:
P00350
Molecular weight:
51481
Reactions
6-phospho-D-gluconate + NADP(+) = D-ribulose 5-phosphate + CO(2) + NADPH.
General function:
Involved in phosphogluconate dehydratase activity
Specific function:
6-phospho-D-gluconate = 2-dehydro-3-deoxy-6- phospho-D-gluconate + H(2)O
Gene Name:
edd
Uniprot ID:
P0ADF6
Molecular weight:
64639
Reactions
6-phospho-D-gluconate = 2-dehydro-3-deoxy-6-phospho-D-gluconate + H(2)O.
General function:
Involved in shikimate kinase activity
Specific function:
ATP + D-gluconate = ADP + 6-phospho-D- gluconate
Gene Name:
idnK
Uniprot ID:
P39208
Molecular weight:
21004
Reactions
ATP + D-gluconate = ADP + 6-phospho-D-gluconate.
General function:
Involved in shikimate kinase activity
Specific function:
ATP + D-gluconate = ADP + 6-phospho-D- gluconate
Gene Name:
gntK
Uniprot ID:
P46859
Molecular weight:
19543
Reactions
ATP + D-gluconate = ADP + 6-phospho-D-gluconate.
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Catalyzes the hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate
Gene Name:
pgl
Uniprot ID:
P52697
Molecular weight:
36308
Reactions
6-phospho-D-glucono-1,5-lactone + H(2)O = 6-phospho-D-gluconate.