Identification
YMDB IDYMDB00140
Name6-Phosphonoglucono-D-lactone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description6-Phosphonoglucono-D-lactone, also known as D-glucono-1,5-lactone 6-phosphate or 6-PGDL, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. 6-Phosphonoglucono-D-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphonoglucono-D-lactone exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholestan-26-oyl-coenzyme A
  • 3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-CoA
  • 6-(dihydrogen phosphate)-(8CI)-D-Gluconic acid delta-lactone
  • 6-(dihydrogen phosphate)-(9CI)-D-Gluconic acid delta-lactone
  • 6-(dihydrogen phosphate)-D-Gluconic acid delta-lactone
  • 6-Pgdl
  • 6-Phospho-D-glucono-1,5-lactone
  • 6-Phosphoglucono-delta-lactone
  • 6-phosphogluconolactone
  • 6-Phosphonoglucono-delta-lactone
  • D-6-phospho-glucono-delta-lactone
  • D-6-phosphoglucono-delta-lactone
  • D-Glucono-1,5-lactone 6-phosphate
  • D-glucono-delta-lactone-6-phosphate
  • delta-Gluconolactone 6-phosphate
  • [(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphate
  • D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphate)
  • 6-Phosphonoglucono-δ-lactone
  • [(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphoric acid
  • D-Gluconate, delta-lactone, 6-(dihydrogen phosphate)
  • D-Gluconate, δ-lactone, 6-(dihydrogen phosphate)
  • D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphoric acid)
  • D-Gluconic acid, δ-lactone, 6-(dihydrogen phosphoric acid)
  • D-Glucono-1,5-lactone 6-phosphoric acid
  • p-Gluconolactone
CAS number2641-81-8
WeightAverage: 258.1199
Monoisotopic: 258.014068462
InChI KeyIJOJIVNDFQSGAB-SQOUGZDYSA-N
InChIInChI=1S/C6H11O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H2,11,12,13)/t2-,3-,4+,5-/m1/s1
IUPAC Name{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name6-phosphogluconolactone
Chemical FormulaC6H11O9P
SMILES[H]O[C@@]1([H])C(=O)O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Gluconolactone
  • Monosaccharide phosphate
  • Delta valerolactone
  • Delta_valerolactone
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Oxane
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility32.6 g/LALOGPS
logP-2ALOGPS
logP-2.9ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)1.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.65 m³·mol⁻¹ChemAxon
Polarizability19.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
  • 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
aldehydo-D-glucose 6-phosphate + NADPNADPH + hydron + 6-Phosphonoglucono-D-lactone
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9410000000-eed74c30dd7f6e1f6308JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0gb9-4962700000-904ef84e4218dd793e1fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0490000000-b7b9499f5fb3885d4a30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r7-5940000000-effb433b86b6c959da1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukc-7900000000-4009a042c78eba5dae17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7290000000-09bacc885b7c74c16eceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5f41258b7bf2096e04fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b3c16e1939174dae85JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5090000000-381acc8a668fbac0de38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9030000000-d9d231d9c36c323e6446JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f53a8156649b945c2aeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-8f89af904744e22d72b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-8d2bf1400d030127126aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-95f15475c3f10c3ac1bdJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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
  • Moir, R. D., Stokes, G. B. (1988). "A spectrophotometric assay for 6-phosphogluconolactonase involving the use of immobilized enzymes to prepare the labile 6-phosphoglucono-delta-lactone substrate." Biochem J 256:69-73.3223913
  • 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
  • Nogae, I., Johnston, M. (1990). "Isolation and characterization of the ZWF1 gene of Saccharomyces cerevisiae, encoding glucose-6-phosphate dehydrogenase." Gene 96:161-169.2269430
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16938
HMDB IDHMDB01127
Pubchem Compound ID439452
Kegg IDC01236
ChemSpider ID24785639
FOODB IDFDB030612
Wikipedia6-phosphogluconolactone
BioCyc IDD-6-P-GLUCONO-DELTA-LACTONE

Enzymes

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 glucose-6-phosphate dehydrogenase activity
Specific function:
D-glucose 6-phosphate + NADP(+) = D-glucono- 1,5-lactone 6-phosphate + NADPH
Gene Name:
ZWF1
Uniprot ID:
P11412
Molecular weight:
57521.10156
Reactions
D-glucose 6-phosphate + NADP(+) → 6-phospho-D-glucono-1,5-lactone + 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.