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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 00:55:05 UTC
Update Date2020-02-26 21:26:21 UTC
HMDB IDHMDB0006334
Secondary Accession Numbers
  • HMDB06334
Metabolite Identification
Common Name3-Dehydro-L-gulonate
Description3-Dehydro-L-gulonate 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. A derivative of L-gulonic acid having a keto group at the 3-position. 3-Dehydro-L-gulonate is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Dehydro-L-gulonate exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752381
Synonyms
ValueSource
3-Dehydro-L-gulonic acidGenerator
L-Xylo-hex-3-ulosonic acidHMDB
Chemical FormulaC6H10O7
Average Molecular Weight194.1394
Monoisotopic Molecular Weight194.042652674
IUPAC Name(2S,4R,5S)-2,4,5,6-tetrahydroxy-3-oxohexanoic acid
Traditional Name3-dehydro-L-gulonic acid
CAS Registry NumberNot Available
SMILES
OC[C@H](O)[C@@H](O)C(=O)[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,5,7-9,11H,1H2,(H,12,13)/t2-,3+,5-/m0/s1
InChI KeyWTAHRPBPWHCMHW-LWKDLAHASA-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-hydroxy acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Keto acid
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 Solubility105 g/LALOGPS
logP-2.6ALOGPS
logP-2.6ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.58 m³·mol⁻¹ChemAxon
Polarizability16.3 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, Positivesplash10-0r29-9200000000-bfa5f284c8a99449827aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00ku-4401960000-e7040dc9b253756697acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-4ee99057131bac58d24bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imi-9600000000-abad7f2422697e8886edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-7128eed92da683639fe8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05bu-9800000000-2f48ad5aa2d38b4abf96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-9500000000-96092591d92e04b163efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9100000000-833ef232e8c397c98dd3Spectrum
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 IDFDB023894
KNApSAcK IDNot Available
Chemspider ID388406
KEGG Compound IDC00618
BioCyc IDNot Available
BiGG ID35509
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439273
PDB IDNot Available
ChEBI ID16142
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
CRYL1
Uniprot ID:
Q9Y2S2
Molecular weight:
35418.91
Reactions
Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADHdetails
Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADH + Hydrogen Iondetails