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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:32 UTC
HMDB IDHMDB01127
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-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 ). The pentose-phosphate pathway provides reductive power and nucleotide precursors to the cell through oxidative and nonoxidative branches. 6-Phosphogluconolactonase is the second enzyme of the oxidative branch and catalyzes the hydrolysis of 6-phosphogluconolactones, the products of glucose 6-phosphate oxidation by glucose-6-phosphate dehydrogenase. By efficiently catalyzing the hydrolysis of d-6PGL, 6-phosphogluconolactonase prevents the reaction between d-6PGL and intracellular nucleophiles; such a reaction would interrupt the functioning of the pentose-phosphate pathway. (PMID 11457850 ).
Structure
Thumb
Synonyms
  1. 6-(Dihydrogen phosphate)-(8CI)-D-Gluconic acid delta-lactone
  2. 6-(Dihydrogen phosphate)-(9CI)-D-Gluconic acid delta-lactone
  3. 6-(Dihydrogen phosphate)-D-Gluconic acid delta-lactone
  4. 6-Pgdl
  5. 6-Phospho-D-glucono-1,5-lactone
  6. 6-Phosphoglucono-delta-lactone
  7. 6-Phosphogluconolactone
  8. 6-Phosphonoglucono-delta-lactone
  9. D-6-Phospho-glucono-delta-lactone
  10. D-6-Phosphoglucono-delta-lactone
  11. D-Glucono-1,5-lactone 6-phosphate
  12. D-Glucono-delta-lactone-6-phosphate
  13. delta-Gluconolactone 6-phosphate
Chemical FormulaC6H11O9P
Average Molecular Weight258.1199
Monoisotopic Molecular Weight258.014068462
IUPAC Name{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxyphosphonic acid
CAS Registry Number2641-81-8
SMILES
O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1O
InChI Identifier
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
InChI KeyIJOJIVNDFQSGAB-SQOUGZDYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • aldonolactone phosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Carboxylic Acid Ester
  • Delta Valerolactone
  • Lactone
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glutathione metabolism
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 Area153.75ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.65ChemAxon
Polarizability19.89ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biofluid Locations
  • Cellular Cytoplasm
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified0.00762 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022440
KNApSAcK IDNot Available
Chemspider ID388559
KEGG Compound IDC01236
BioCyc IDD-6-P-GLUCONO-DELTA-LACTONE
BiGG ID37157
Wikipedia Link6-phosphogluconolactone
NuGOwiki LinkHMDB01127
Metagene LinkHMDB01127
METLIN ID6022
PubChem Compound439452
PDB IDNot Available
ChEBI ID16938
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. Beutler E, Kuhl W: Characteristics and significance of the reverse glucose-6-phosphate dehydrogenase reaction. J Lab Clin Med. 1986 Jun;107(6):502-7. Pubmed: 3711719
  3. Rakitzis ET, Papandreou P: Kinetic analysis of 6-phosphogluconolactone hydrolysis in hemolysates. Biochem Mol Biol Int. 1995 Nov;37(4):747-55. Pubmed: 8589648
  4. 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

Enzymes

General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:
PGLS
Uniprot ID:
O95336
Molecular weight:
27546.495
Reactions
6-Phosphonoglucono-D-lactone + Water → 6-Phosphogluconic aciddetails
General function:
Involved in glucose-6-phosphate dehydrogenase activity
Specific function:
Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
Gene Name:
G6PD
Uniprot ID:
P11413
Molecular weight:
62467.88
Reactions
Beta-D-Glucose 6-phosphate + NADP → 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Iondetails
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Oxidizes glucose-6-phosphate and glucose, as well as other hexose-6-phosphates.
Gene Name:
H6PD
Uniprot ID:
O95479
Molecular weight:
88891.99
Reactions
Glucose 6-phosphate + NAD(P)(+) → 6-Phosphonoglucono-D-lactone + NAD(P)Hdetails
6-Phosphonoglucono-D-lactone + Water → 6-Phosphogluconic aciddetails
Beta-D-Glucose 6-phosphate + NADP → 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Iondetails