Showing Compound Card for 6-Phosphonoglucono-D-lactone (CDB005253)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:24:40 UTC
Updated at2020-11-18 16:39:36 UTC
CannabisDB IDCDB005253
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name6-Phosphonoglucono-D-lactone
Description6-Phosphonoglucono-D-lactone, also known as D-glucono-1,5-lactone 6-phosphate 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. An aldonolactone phosphate comprising D-glucono-1,5-lactone having the phosphate group at the 6-position. 6-Phosphonoglucono-D-lactone is 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. Within humans, 6-phosphonoglucono-D-lactone participates in a number of enzymatic reactions. In particular, 6-phosphonoglucono-D-lactone can be converted into 6-phosphogluconic acid; which is mediated by the enzyme 6-phosphogluconolactonase. In addition, 6-phosphonoglucono-D-lactone can be biosynthesized from β-D-glucose 6-phosphate; which is mediated by the enzyme glucose-6-phosphate 1-dehydrogenase. In humans, 6-phosphonoglucono-D-lactone is involved in the metabolic disorder called the warburg effect pathway. Outside of the human body, 6-Phosphonoglucono-D-lactone has been detected, but not quantified in, several different foods, such as beans, soft-necked garlics, peppermints, sparkleberries, and brazil nuts. This could make 6-phosphonoglucono-D-lactone a potential biomarker for the consumption of these foods. 6-Phosphonoglucono-D-lactone is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight258.12
Monoisotopic Molecular Weight258.0141
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:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS6-Phosphonoglucono-D-lactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9410000000-eed74c30dd7f6e1f6308Spectrum
Predicted GC-MS6-Phosphonoglucono-D-lactone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gb9-4962700000-904ef84e4218dd793e1fSpectrum
Predicted GC-MS6-Phosphonoglucono-D-lactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0490000000-b7b9499f5fb3885d4a302015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r7-5940000000-effb433b86b6c959da1d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukc-7900000000-4009a042c78eba5dae172015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7290000000-09bacc885b7c74c16ece2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5f41258b7bf2096e04fd2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b3c16e1939174dae852015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5090000000-381acc8a668fbac0de382021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9030000000-d9d231d9c36c323e64462021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f53a8156649b945c2aee2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-8f89af904744e22d72b52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-8d2bf1400d030127126a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-95f15475c3f10c3ac1bd2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
6-phosphogluconolactonasePGLS19p13.2O95336 details
Glucose-6-phosphate 1-dehydrogenaseG6PDXq28P11413 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001127
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030612
KNApSAcK IDNot Available
Chemspider ID388559
KEGG Compound IDC01236
BioCyc IDD-6-P-GLUCONO-DELTA-LACTONE
BiGG ID37157
Wikipedia LinkNot Available
METLIN ID6022
PubChem Compound439452
PDB IDNot Available
ChEBI ID16938
References
General ReferencesNot Available

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
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