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Showing metabocard for 6-Phosphonoglucono-D-lactone (HMDB0001127)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:44 UTC
HMDB IDHMDB0001127
Secondary Accession Numbers
  • HMDB01127
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
Data?1563860684
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Phospho-D-glucono-1,5-lactoneChEBI
6-Phosphonoglucono-delta-lactoneChEBI
[(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphateChEBI
D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphate)ChEBI
D-Glucono-1,5-lactone 6-phosphateChEBI
6-Phosphonoglucono-δ-lactoneGenerator
[(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphoric acidGenerator
D-Gluconate, delta-lactone, 6-(dihydrogen phosphate)Generator
D-Gluconate, δ-lactone, 6-(dihydrogen phosphate)Generator
D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphoric acid)Generator
D-Gluconic acid, δ-lactone, 6-(dihydrogen phosphoric acid)Generator
D-Glucono-1,5-lactone 6-phosphoric acidGenerator
6-(Dihydrogen phosphate)-(8ci)-D-gluconic acid delta-lactoneHMDB
6-(Dihydrogen phosphate)-(9ci)-D-gluconic acid delta-lactoneHMDB
6-(Dihydrogen phosphate)-D-gluconic acid delta-lactoneHMDB
6-PGDLHMDB
6-Phosphoglucono-delta-lactoneHMDB
6-PhosphogluconolactoneHMDB
D-6-Phospho-glucono-delta-lactoneHMDB
D-6-Phosphoglucono-delta-lactoneHMDB
D-Glucono-delta-lactone-6-phosphateHMDB
delta-Gluconolactone 6-phosphateHMDB
p-GluconolactoneHMDB
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 Name6-phosphogluconolactone
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
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 Area153.75 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9410000000-eed74c30dd7f6e1f6308JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0gb9-4962700000-904ef84e4218dd793e1fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0490000000-b7b9499f5fb3885d4a30JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r7-5940000000-effb433b86b6c959da1dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukc-7900000000-4009a042c78eba5dae17JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7290000000-09bacc885b7c74c16eceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5f41258b7bf2096e04fdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b3c16e1939174dae85JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen Locations
  • Cellular Cytoplasm
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022440
KNApSAcK IDNot Available
Chemspider ID388559
KEGG Compound IDC01236
BioCyc IDNot Available
BiGG ID37157
Wikipedia LinkNot Available
METLIN ID6022
PubChem Compound439452
PDB IDNot Available
ChEBI ID16938
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot 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 ]
  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;2:18. [PubMed:15882454 ]
  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

Enzyme Details
1. 6-phosphogluconolactonase
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
Enzyme Details
2. Glucose-6-phosphate 1-dehydrogenase
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
Enzyme Details
3. GDH/6PGL endoplasmic bifunctional protein
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