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Showing Compound 2,3-Diketo-L-gulonate (FDB023950)

Record Information
Version1.0
Creation date2011-09-21 00:37:21 UTC
Update date2024-11-29 22:26:18 UTC
Primary IDFDB023950
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.-). [HMDB] Diketogulonic 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) [HMDB]
CAS Number3445-22-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
Chemical FormulaC6H8O7
IUPAC name(5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC[C@H](O)C(O)C(=O)C(=O)C(O)=O
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,3-Diketo-L-gulonate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0nn9-9200000000-1cbed9b2b56caa085c4aSpectrum
Predicted GC-MS2,3-Diketo-L-gulonate, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02or-7339800000-1615efb2d0feaa5735eaSpectrum
Predicted GC-MS2,3-Diketo-L-gulonate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-1900000000-1d6c68c73855ddcddb542017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08mi-9500000000-c792fe4653b44e9ab3722017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-16a4d7310299656e77442017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0g4l-9700000000-6d882e161ed0ab1a76562017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9300000000-c5167767732d60eead4b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-f6c0690482bc1a9402372017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01c0-6900000000-f68a48e03dbb51e873732021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-11ou-9500000000-f51f88025205022293152021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btd-9000000000-b607173f6a4870d24b5f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005j-7900000000-095b22b39dbcc6d9fa052021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-05380c64aede8d94e31b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-84c78a8bd0634d2dfffc2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC04575
Pubchem Compound ID53477844
Pubchem Substance IDNot Available
ChEBI ID15622
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06511
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45750
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference