Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120395
Identification
Name: 2,3-dioxo-L-gulonate
Description:A dioxo monocarboxylic acid anion that is the conjugate base of 2,3-diketogulonic acid, and the major species at pH 7.3.
Structure
Thumb
Synonyms:
  • 2,3-diketo-L-gulonate
  • 2,3-dioxo-L-gulonate(1−)
  • 2,3-dioxo-L-gulonic
Chemical Formula: C6H7O7
Average Molecular Weight: 191.117
Monoisotopic Molecular Weight: 192.02701
InChI Key: GJQWCDSAOUMKSE-STHAYSLISA-M
InChI:InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/p-1/t2-,3+/m0/s1
CAS number: 3409-57-2
IUPAC Name:(4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate
Traditional IUPAC Name: diketogulonic acid
SMILES:C(C(C(C(C(C([O-])=O)=O)=O)O)O)O
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic oxygen compounds
Sub ClassOrganooxygen compounds
Direct Parent Sugar 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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
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
Polarizability15.88 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Linster CL, Van Schaftingen E (2007)Vitamin C. Biosynthesis, recycling and degradation in mammals. The FEBS journal 274, Pubmed: 17222174
    • Kärkönen A, Fry SC (2006)Effect of ascorbate and its oxidation products on H2O2 production in cell-suspension cultures of Picea abies and in the absence of cells. Journal of experimental botany 57, Pubmed: 16698813
    • Shamsi FA, Partal A, Sady C, Glomb MA, Nagaraj RH (1998)Immunological evidence for methylglyoxal-derived modifications in vivo. Determination of antigenic epitopes. The Journal of biological chemistry 273, Pubmed: 9506998
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC57441
    HMDBHMDB05971
    BIGG45750
    CHEMSPIDER20015966
    CHEBI57441
    PUBCHEM21145097
    LIGAND-CPDC04575