Human Metabolome Database Version 3.5

Showing metabocard for 6-Phosphonoglucono-D-lactone (HMDB01127)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:32 -0600
HMDB ID HMDB01127
Secondary Accession Numbers None
Metabolite Identification
Common 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 Link_out). 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H11O9P
Average Molecular Weight 258.1199
Monoisotopic Molecular Weight 258.014068462
IUPAC Name {[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxyphosphonic acid
CAS Registry Number 2641-81-8
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 Key IJOJIVNDFQSGAB-SQOUGZDYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
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 Parent Hexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glutathione metabolism
Application Not Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 32.6 g/L ALOGPS
LogP -1.99 ALOGPS
LogP -2.9 ChemAxon
LogS -0.90 ALOGPS
pKa (strongest acidic) 1.3 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 153.75 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 45.65 ChemAxon
Polarizability 19.89 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biofluid Locations
  • Cellular Cytoplasm
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cellular Cytoplasm Detected and Quantified
0.00762 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022440
KNApSAcK ID Not Available
Chemspider ID 388559 Link_out
KEGG Compound ID C01236 Link_out
BioCyc ID D-6-P-GLUCONO-DELTA-LACTONE Link_out
BiGG ID 37157 Link_out
Wikipedia Link 6-phosphogluconolactone Link_out
NuGOwiki Link HMDB01127 Link_out
Metagene Link HMDB01127 Link_out
METLIN ID 6022 Link_out
PubChem Compound 439452 Link_out
PDB ID Not Available
ChEBI ID 16938 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. 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 Link_out
  2. 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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: 6-phosphogluconolactonase
Reactions:
6-Phosphonoglucono-D-lactone + Water unknown 6-Phosphogluconic acid details
Gene Name: PGLS
Uniprot ID: O95336 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate 1-dehydrogenase
Reactions:
Beta-D-Glucose 6-phosphate + NADP unknown 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Ion details
Gene Name: G6PD
Uniprot ID: P11413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GDH/6PGL endoplasmic bifunctional protein
Reactions:
Glucose 6-phosphate + NAD(P)(+) unknown 6-Phosphonoglucono-D-lactone + NAD(P)H details
6-Phosphonoglucono-D-lactone + Water unknown 6-Phosphogluconic acid details
Beta-D-Glucose 6-phosphate + NADP unknown 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Ion details
Gene Name: H6PD
Uniprot ID: O95479 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA