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Identification
YMDB IDYMDB00218
Name6-Phosphogluconic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description6-Phosphogluconic acid, also known as 6-phospho-D-gluconate or gluconate 6-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 6-Phosphogluconic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphogluconic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 6-O-phosphono-D-gluconic acid
  • 6-p-gluconate
  • 6-Phospho-D-gluconate
  • 6-Phospho-D-gluconic acid
  • 6-phosphogluconate
  • 6-phosphogluconic acid
  • d-gluconate 6-phosphate
  • D-Gluconic acid 6-(dihydrogen phosphate)
  • D-Gluconic acid 6-phosphate
  • gluconic acid-6-phosphate
  • Gluconate 6-phosphate
CAS number921-62-0
WeightAverage: 276.1352
Monoisotopic: 276.024633148
InChI KeyBIRSGZKFKXLSJQ-SQOUGZDYSA-N
InChIInChI=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
IUPAC Name(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid
Traditional IUPAC Name6-phosphogluconic acid
Chemical FormulaC6H13O10P
SMILES[H]OC(=O)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility20.7 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.14 m³·mol⁻¹ChemAxon
Polarizability21.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Pentose phosphate pathwayec00030 Map00030
SMPDB ReactionsNot Available
KEGG Reactions
water + 6-Phosphonoglucono-D-lactone6-Phosphogluconic acid + hydron
6-Phosphogluconic acid + NADPCarbon dioxide + NADPH + D-ribulose 5-phosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
200 ± 100 µM Minimal medium supplemented with ammonia salts and (glucose or galactose)aerobic;growing cellsBaker's yeastPMID: 4578278
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0uxu-0933000000-d0c837bb667abbae2ce0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-00ks-1978000000-c7702d284ad9f06bb5c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uxu-0933000000-d0c837bb667abbae2ce0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ks-1978000000-c7702d284ad9f06bb5c0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9430000000-e4198ba354325082e116JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00dl-7192047000-e8fa0bd25a22fa6fd28bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dj-5090000000-a1b0f01abec0e4fb22c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b62JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff41JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d218JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d218JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f532JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e12603JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e1b81e634eb90448b9cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2590000000-53a3a79c2cc73c243e4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6v-7920000000-e9b87a1b1cd046187a03JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-299a98a9b8ecad68997dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9830000000-f784c955d104bea3213fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-bffd36c521b6f41716d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d27f7e55395c8a6e1547JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • KAWADA, M., KAGAWA, Y., TAKIGUCHI, H., SHIMAZONO, N. (1962). "Purification of 6-phosphogluconolactonase from rat liver and yeast; its separation from gluconolactonase." Biochim Biophys Acta 57:404-407.14454532
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID48928
HMDB IDHMDB01316
Pubchem Compound ID91493
Kegg IDC00345
ChemSpider ID82615
FOODB IDFDB030611
Wikipedia6-Phosphogluconic_acid
BioCyc IDCPD-2961

Enzymes

General function:
Involved in ATP binding
Specific function:
ATP + D-gluconate = ADP + 6-phospho-D- gluconate
Gene Name:
Not Available
Uniprot ID:
Q03786
Molecular weight:
22174.5
Reactions
ATP + D-gluconate → ADP + 6-phospho-D-gluconate.
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6- phosphogluconate
Gene Name:
SOL4
Uniprot ID:
P53315
Molecular weight:
28447.5
Reactions
6-phospho-D-glucono-1,5-lactone + H(2)O → 6-phospho-D-gluconate.
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
May be involved in regulation of tRNA subcellular distribution
Gene Name:
SOL1
Uniprot ID:
P50278
Molecular weight:
35652.19922
Reactions
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
May be involved in regulation of tRNA subcellular distribution
Gene Name:
SOL2
Uniprot ID:
P37262
Molecular weight:
34500.89844
Reactions
General function:
Involved in oxidoreductase activity
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:
GND1
Uniprot ID:
P38720
Molecular weight:
53542.69922
Reactions
6-phospho-D-gluconate + NADP(+) → D-ribulose 5-phosphate + CO(2) + NADPH.
General function:
Involved in oxidoreductase activity
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:
GND2
Uniprot ID:
P53319
Molecular weight:
53922.30078
Reactions
6-phospho-D-gluconate + NADP(+) → D-ribulose 5-phosphate + CO(2) + NADPH.
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6- phosphogluconate
Gene Name:
SOL3
Uniprot ID:
P38858
Molecular weight:
27784.19922
Reactions
6-phospho-D-glucono-1,5-lactone + H(2)O → 6-phospho-D-gluconate.