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
Version3.6
Creation Date2007-05-23 00:55:05 UTC
Update Date2016-02-11 01:07:29 UTC
HMDB IDHMDB06334
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Dehydro-L-gulonate
Description3-Dehydro-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 3-Dehydro-L-gulonate is the 4th to last step in the synthesis of D-Xylulose 5-phosphate and is converted from 2,3-Diketo-L-gulonate via the enzyme 3-dehydro-L-gulonate 2-dehydrogenase (EC 1.1.1.130). It is then converted to 3-Dehydro-L-gulonate 6-phosphate via the enzyme L-xylulokinase (EC 2.7.1.53).
Structure
Thumb
Synonyms
ValueSource
3-dehydro-L-GulonateChEBI
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 KeyInChIKey=WTAHRPBPWHCMHW-LWKDLAHASA-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
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Keto acid
  • Hydroxy acid
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-hydroxy 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 Descriptors
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 Solubility105.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.58 m3·mol-1ChemAxon
Polarizability16.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-4ee99057131bac58d24bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imi-9600000000-abad7f2422697e8886edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-7128eed92da683639fe8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05bu-9800000000-2f48ad5aa2d38b4abf96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-9500000000-96092591d92e04b163efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9100000000-833ef232e8c397c98dd3View in MoNA
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 IDFDB023894
KNApSAcK IDNot Available
Chemspider ID388406
KEGG Compound IDC00618
BioCyc IDNot Available
BiGG ID35509
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06334
Metagene LinkHMDB06334
METLIN IDNot Available
PubChem Compound439273
PDB IDNot Available
ChEBI ID16142
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