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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:27:39 UTC
HMDB IDHMDB0001353
Secondary Accession Numbers
  • HMDB01353
Metabolite Identification
Common Name2-Keto-3-deoxy-D-gluconic acid
Description2-keto-3-deoxy-d-gluconic acid, also known as 2-dehydro-3-deoxy-D-galactonate or 3-deoxy-2-oxo-D-gluconate, belongs to medium-chain keto acids and derivatives class of compounds. Those are keto acids with a 6 to 12 carbon atoms long side chain. Thus, 2-keto-3-deoxy-d-gluconic acid is considered to be a fatty acid lipid molecule. 2-keto-3-deoxy-d-gluconic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, 2-keto-3-deoxy-d-gluconic acid is primarily located in the cytoplasm (predicted from logP). 2-keto-3-deoxy-d-gluconic acid exists in all living organisms, ranging from bacteria to humans. 2-Keto-3-deoxy-D-gluconic acid is a substrate for Fructose-bisphosphate aldolase A..
Structure
Thumb
Synonyms
ValueSource
2-oxo-3-Deoxygalactonic acidMeSH
3-Deoxy-D-threo-hexulosonic acidMeSH
Chemical FormulaC6H10O6
Average Molecular Weight178.14
Monoisotopic Molecular Weight178.047738052
IUPAC Name(4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid
Traditional Name(4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid
CAS Registry Number17510-99-5
SMILES
OC[C@@H](O)[C@H](O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/t3-,5-/m1/s1
InChI KeyWPAMZTWLKIDIOP-NQXXGFSBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility134 g/LALOGPS
logP-1.9ALOGPS
logP-1.8ChemAxon
logS-0.12ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.32 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cnc-9200000000-ca7affd58ffff99e944aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0kbf-9015500000-ab605becee17a221c24eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fu-1900000000-16261982c6a9c806a823View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p6-7900000000-504d11f169911538cb06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dv-9200000000-8845066b3c1b409ba899View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-be420c7266318ce9735aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9400000000-fd920a23173f050b910aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9200000000-c9791ea5084cab37fd9fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationNot 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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01216
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound194024
PDB IDNot Available
ChEBI ID17028
References
Synthesis ReferencePlantier-Royon, Richard; Anker, Daniel; Robert-Baudouy, , Janine. New synthesis of 3-deoxy-D-erythro-2-hexulosonic acid (KDG) from D-glucose. Journal of Carbohydrate Chemistry (1991), 10(2), 239-49.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available