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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 13:08:48 UTC
Update Date2020-02-26 21:26:28 UTC
HMDB IDHMDB0006511
Secondary Accession Numbers
  • HMDB06511
Metabolite Identification
Common Name2,3-Diketo-L-gulonate
Description2,3-Diketo-L-gulonate, also known as 2,3-diketo-L-gulonic acid, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. The degradation pathway of vitamin C continues to produce l-erythrulose and oxalate as final products. 2,3-Diketo-L-gulonate is an extremely weak basic (essentially neutral) compound (based on its pKa). A major catabolic event in man is the cleavage of the molecule (presumably a spontaneous cleavage of DKG) between C2 and C3, with little if any decarboxylation. 2,3-Diketo-L-gulonate (DKG) is a metabolite of the degradation of vitamin C, the nonenzymatic hydrolysis-product of dehydroascorbate. Dehydroascorbate can be reduced back to ascorbate or hydrolyzed to DKG; the latter reaction is irreversible and DKG is devoid of antiscorbutic activity. The oxalate formed in this way may contribute to the formation of kidney stones in susceptible individuals. However, the association between ascorbate supplementation and increased risk of kidney stone formation remains a matter of controversy.
Structure
Data?1582752388
Synonyms
ValueSource
2,3-Diketo-L-gulonic acidGenerator
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoateHMDB
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acidHMDB
2,3-Diketo-L gulonic acidHMDB
2,3-Diketogulonic acidHMDB
Diketogulonic acidHMDB
L-Threo-2,3-hexodiulosonic acidHMDB
L-Threo-hexo-2,3-diulosonic acidHMDB
Chemical FormulaC6H8O7
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
IUPAC Name(5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
Traditional Name(5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
CAS Registry Number3445-22-5
SMILES
OC[C@H](O)C(O)C(=O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3?/m0/s1
InChI KeyGJQWCDSAOUMKSE-SCQFTWEKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Medium-chain keto acid
  • Beta-keto acid
  • Sugar acid
  • Acyloin
  • Alpha-keto acid
  • Alpha-diketone
  • Beta-hydroxy ketone
  • Keto acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

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 Solubility59.9 g/LALOGPS
logP-1.8ALOGPS
logP-1.6ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.04 m³·mol⁻¹ChemAxon
Polarizability15.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nn9-9200000000-1cbed9b2b56caa085c4aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-02or-7339800000-1615efb2d0feaa5735eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-1900000000-1d6c68c73855ddcddb54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08mi-9500000000-c792fe4653b44e9ab372Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-16a4d7310299656e7744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0g4l-9700000000-6d882e161ed0ab1a7656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9300000000-c5167767732d60eead4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-f6c0690482bc1a940237Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023950
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04575
BioCyc IDNot Available
BiGG ID45750
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477844
PDB IDNot Available
ChEBI ID15622
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available