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Record Information
Version3.6
Creation Date2007-05-23 13:08:48 UTC
Update Date2016-02-11 01:07:33 UTC
HMDB IDHMDB06511
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3-Diketo-L-gulonate
Description2,3-Diketo-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 2,3-Diketo-L-gulonate is produced from Dehydroascorbate and then converted to L-Xylonate via the enzyme Lyases (EC 4.1.1.-).
Structure
Thumb
Synonyms
ValueSource
(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 KeyInChIKey=GJQWCDSAOUMKSE-SCQFTWEKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Medium-chain keto acid
  • Sugar acid
  • Beta-keto acid
  • Fatty acyl
  • Monosaccharide
  • Keto acid
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-diketone
  • Alpha-keto acid
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.04 m3·mol-1ChemAxon
Polarizability15.77 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023950
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04575
BioCyc ID2,3-diketo-l-gulonate
BiGG ID45750
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06511
Metagene LinkHMDB06511
METLIN IDNot Available
PubChem Compound53477844
PDB IDNot Available
ChEBI ID15622
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available