6-Phosphonoglucono-D-lactone (PAMDB000264)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000264
Identification
Name: 6-Phosphonoglucono-D-lactone
Description:6-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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 258.1199
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Gluconolactones
Alternative Parents
Substituents
  • Gluconolactone
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Delta_valerolactone
  • Delta valerolactone
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Polyol
  • Lactone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility32.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.65 m3·mol-1ChemAxon
Polarizability19.89 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acid + Hydrogen ion
Glucose 6-phosphate + NADP <> 6-Phosphonoglucono-D-lactone + Hydrogen ion + NADPH
6-Phosphonoglucono-D-lactone + Water <> 6-Phosphogluconic acid
beta-D-Glucose 6-phosphate + NADP <> 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion
Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH
beta-D-Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion + NADPH
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
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