6-Phosphonoglucono-D-lactone (CHEM035086)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:28:43 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035086
Identification
Common Name6-Phosphonoglucono-D-lactone
ClassSmall Molecule
Description6-Phosphonoglucono-D-lactone, also known as 6-phosphonoglucono-d-lactone or 6-PGDL, 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. 6-Phosphonoglucono-D-lactone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphonoglucono-D-lactone exists in all living species, ranging from bacteria to humans. 6-Phosphonoglucono-D-lactone participates in a number of enzymatic reactions, within cattle. In particular, 6-Phosphonoglucono-D-lactone can be converted into 6-phosphogluconic acid through the action of the enzyme 6-phosphogluconolactonase. In addition, 6-Phosphonoglucono-D-lactone can be biosynthesized from Beta-D-glucose 6-phosphate; which is mediated by the enzyme glucose-6-phosphate 1-dehydrogenase. In cattle, 6-phosphonoglucono-D-lactone is involved in the metabolic pathway called cancer (via the Warburg effect).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass258.120 g/mol
Monoisotopic Mass258.014 g/mol
CAS Registry Number2641-81-8
IUPAC Name{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid
Traditional Name6-phosphogluconolactone
SMILESO[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability19.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9410000000-eed74c30dd7f6e1f6308Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0gb9-4962700000-904ef84e4218dd793e1fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0490000000-b7b9499f5fb3885d4a30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r7-5940000000-effb433b86b6c959da1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukc-7900000000-4009a042c78eba5dae17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7290000000-09bacc885b7c74c16eceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5f41258b7bf2096e04fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b3c16e1939174dae85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5090000000-381acc8a668fbac0de38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9030000000-d9d231d9c36c323e6446Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f53a8156649b945c2aeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-8f89af904744e22d72b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-8d2bf1400d030127126aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-95f15475c3f10c3ac1bdSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001127
FooDB IDFDB030612
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID37157
BioCyc IDD-6-P-GLUCONO-DELTA-LACTONE
METLIN ID6022
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID388559
ChEBI ID16938
PubChem Compound ID439452
Kegg Compound IDC01236
YMDB IDYMDB00140
ECMDB IDECMDB01127
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
3. Rakitzis ET, Papandreou P: Kinetic analysis of 6-phosphogluconolactone hydrolysis in hemolysates. Biochem Mol Biol Int. 1995 Nov;37(4):747-55.
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.