Record Information
Version2.0
Creation Date2012-05-31 13:45:48 -0600
Update Date2015-06-03 15:53:45 -0600
Secondary Accession Numbers
  • ECMDB01127
Identification
Name:6-Phosphonoglucono-D-lactone
Description6-phosphoglucono-delta-lactone (d-6PGL) is the immediate product of the Glucose-6-phosphate dehydrogenase (G-6-PD), the first enzyme of the hexose monophosphate pathway. (PMID 3711719)
Structure
Thumb
Synonyms:
  • 6-(Dihydrogen phosphate)-(8CI)-D-Gluconate delta-lactone
  • 6-(Dihydrogen phosphate)-(8ci)-D-gluconate δ-lactone
  • 6-(Dihydrogen phosphate)-(8CI)-D-Gluconic acid delta-lactone
  • 6-(Dihydrogen phosphate)-(9CI)-D-Gluconate D-lactone
  • 6-(Dihydrogen phosphate)-(9ci)-D-gluconate delta-lactone
  • 6-(Dihydrogen phosphate)-(9ci)-D-gluconate δ-lactone
  • 6-(Dihydrogen phosphate)-(9CI)-D-Gluconic acid D-lactone
  • 6-(dihydrogen phosphate)-(9CI)-D-Gluconic acid delta-lactone
  • 6-(Dihydrogen phosphate)-D-Gluconate delta-lactone
  • 6-(Dihydrogen phosphate)-D-gluconate δ-lactone
  • 6-(Dihydrogen phosphate)-D-Gluconic acid delta-lactone
  • 6-(Dihydrogen phosphoric acid)-(8ci)-D-gluconic acid delta-lactone
  • 6-(Dihydrogen phosphoric acid)-(8ci)-D-gluconic acid δ-lactone
  • 6-(Dihydrogen phosphoric acid)-(9ci)-D-gluconic acid D-lactone
  • 6-(Dihydrogen phosphoric acid)-(9ci)-D-gluconic acid delta-lactone
  • 6-(Dihydrogen phosphoric acid)-(9ci)-D-gluconic acid δ-lactone
  • 6-(Dihydrogen phosphoric acid)-D-gluconic acid delta-lactone
  • 6-(Dihydrogen phosphoric acid)-D-gluconic acid δ-lactone
  • 6-Pgdl
  • 6-Phospho-D-glucono-1,5-lactone
  • 6-Phosphoglucono-delta-lactone
  • 6-phosphoglucono-δ-Lactone
  • 6-Phosphogluconolactone
  • 6-Phosphonoglucono-delta-lactone
  • 6-phosphonoglucono-δ-Lactone
  • D-6-P-glucono-δ-lactone
  • D-6-P-Glucono-delta-lactone
  • D-6-P-glucono-δ-Lactone
  • D-6-phospho-glucono-δ-lactone
  • D-6-Phospho-glucono-delta-lactone
  • D-6-phospho-glucono-δ-Lactone
  • D-6-phosphoglucono-δ-lactone
  • D-6-Phosphoglucono-delta-lactone
  • D-6-phosphoglucono-δ-Lactone
  • D-glucono-δ-lactone-6-phosphate
  • D-glucono-δ-lactone-6-phosphoric acid
  • D-Glucono-1,5-lactone 6-phosphate
  • D-glucono-1,5-Lactone 6-phosphoric acid
  • D-Glucono-1,5-lactone-6-phosphate
  • D-glucono-1,5-Lactone-6-phosphoric acid
  • D-Glucono-delta-lactone-6-phosphate
  • D-glucono-delta-Lactone-6-phosphoric acid
  • D-glucono-δ-Lactone-6-phosphate
  • D-glucono-δ-Lactone-6-phosphoric acid
  • Delta-Gluconolactone 6-phosphate
  • delta-Gluconolactone 6-phosphoric acid
  • δ-Gluconolactone 6-phosphate
  • δ-Gluconolactone 6-phosphoric acid
Chemical Formula:C6H11O9P
Weight:Average: 258.1199
Monoisotopic: 258.014068462
InChI Key:IJOJIVNDFQSGAB-SQOUGZDYSA-N
InChI:InChI=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
CAS number:2641-81-8
IUPAC Name:{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:6-phosphogluconolactone
SMILES:O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1O
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
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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:Cytoplasm
Reactions:
SMPDB Pathways:
Glutathione metabolismPW000833 ThumbThumb?image type=greyscaleThumb?image type=simple
Pentose PhosphatePW000893 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9410000000-eed74c30dd7f6e1f6308View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0gb9-4962700000-904ef84e4218dd793e1fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0490000000-b7b9499f5fb3885d4a30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r7-5940000000-effb433b86b6c959da1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukc-7900000000-4009a042c78eba5dae17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7290000000-09bacc885b7c74c16eceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5f41258b7bf2096e04fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b3c16e1939174dae85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5090000000-381acc8a668fbac0de38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9030000000-d9d231d9c36c323e6446View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f53a8156649b945c2aeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-8f89af904744e22d72b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-8d2bf1400d030127126aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-95f15475c3f10c3ac1bdView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Beutler, E., Kuhl, W. (1986). "Characteristics and significance of the reverse glucose-6-phosphate dehydrogenase reaction." J Lab Clin Med 107:502-507. Pubmed: 3711719
  • 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
  • Miclet E, Stoven V, Michels PA, Opperdoes FR, Lallemand JY, Duffieux F: NMR spectroscopic analysis of the first two steps of the pentose-phosphate pathway elucidates the role of 6-phosphogluconolactonase. J Biol Chem. 2001 Sep 14;276(37):34840-6. Epub 2001 Jul 16. Pubmed: 11457850
  • 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
  • Rakitzis ET, Papandreou P: Kinetic analysis of 6-phosphogluconolactone hydrolysis in hemolysates. Biochem Mol Biol Int. 1995 Nov;37(4):747-55. Pubmed: 8589648
  • 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)Not Available
External Links:
ResourceLink
CHEBI ID16938
HMDB IDHMDB01127
Pubchem Compound ID439452
Kegg IDC01236
ChemSpider ID388559
Wikipedia6-phosphogluconolactone
BioCyc IDD-6-P-GLUCONO-DELTA-LACTONE
EcoCyc IDD-6-P-GLUCONO-DELTA-LACTONE

Enzymes

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:
zwf
Uniprot ID:
P0AC53
Molecular weight:
55704
Reactions
D-glucose 6-phosphate + NADP(+) = 6-phospho-D-glucono-1,5-lactone + NADPH.
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.