You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
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
Polarizability19.89 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 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
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.