You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-04-12 19:03:31 UTC
Update Date2017-12-07 01:55:34 UTC
HMDB IDHMDB0005971
Secondary Accession Numbers
  • HMDB05971
Metabolite Identification
Common NameDiketogulonic acid
DescriptionDiketogulonic acid (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 degradation pathway of vitamin C continues to produce l-erythrulose and oxalate as final products. DKG appears in human urine and represents approximately 20% of the vitamin C by-products (oxalate being approximately 44% and dehydroascorbate 20%). 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. 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. (PMID: 16698813 , 17222174 )
Structure
Thumb
Synonyms
ValueSource
(4R,5S)-2,3-dioxo-4,5,6-Trihydroxyhexanoic acidChEBI
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoateChEBI
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acidChEBI
2,3-diketo-L-GulonateChEBI
2,3-diketo-L-Gulonic acidChEBI
2,3-dioxo-2,3-Dideoxy-L-gulonic acidChEBI
2,3-L-Diketogulonic acidChEBI
diketo-L-Gulonic acidChEBI
L-threo-(2,3)-HexodiulosonsaeureChEBI
L-threo-2,3-Hexodiurosonic acidChEBI
threo-2,3-Hexodiulosonic acidChEBI
(4R,5S)-2,3-dioxo-4,5,6-TrihydroxyhexanoateGenerator
DiketogulonateGenerator
2,3-dioxo-2,3-Dideoxy-L-gulonateGenerator
2,3-L-DiketogulonateGenerator
diketo-L-GulonateGenerator
L-threo-2,3-HexodiurosonateGenerator
threo-2,3-HexodiulosonateGenerator
2,3-Diketogulonic acidHMDB
2,3-dioxo-D-GulonateHMDB
L-threo-2,3-Hexodiulosonic acidHMDB
L-threo-hexo-2,3-Diulosonic acidHMDB
Acid, 2,3-diketogulonicMeSH
2,3 Diketogulonic acidMeSH
Chemical FormulaC6H8O7
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
IUPAC Name(4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
Traditional Namediketogulonic acid
CAS Registry Number3409-57-2
SMILES
OC[C@H](O)[C@@H](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-STHAYSLISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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 Descriptors
Ontology
Disposition

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
Polarizability15.88 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nn9-9200000000-1cbed9b2b56caa085c4aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-02or-7339800000-1615efb2d0feaa5735eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-1900000000-1d6c68c73855ddcddb54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08mi-9500000000-c792fe4653b44e9ab372View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-16a4d7310299656e7744View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0g4l-9700000000-6d882e161ed0ab1a7656View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9300000000-c5167767732d60eead4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-f6c0690482bc1a940237View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389343
KEGG Compound IDC04575
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440390
PDB IDNot Available
ChEBI ID15622
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Linster CL, Van Schaftingen E: Vitamin C. Biosynthesis, recycling and degradation in mammals. FEBS J. 2007 Jan;274(1):1-22. [PubMed:17222174 ]
  2. Karkonen A, Fry SC: Effect of ascorbate and its oxidation products on H2O2 production in cell-suspension cultures of Picea abies and in the absence of cells. J Exp Bot. 2006;57(8):1633-44. Epub 2006 May 12. [PubMed:16698813 ]