2-dehydro-3-deoxy-D-gluconate (PAMDB120566)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120566
Identification
Name: 2-dehydro-3-deoxy-D-gluconate
Description:The conjugate base of 2-dehydro-3-deoxy-D-gluconic acid; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-dehydro-3-deoxy-D-gluconate
  • 2-dehydro-3-deoxy-D-gluconate anion
  • 2-dehydro-3-deoxy-D-gluconate(1−)
Chemical Formula: C6H9O6
Average Molecular Weight: 177.133
Monoisotopic Molecular Weight: 178.04774
InChI Key: WPAMZTWLKIDIOP-WVZVXSGGSA-M
InChI: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)/p-1/t3-,5+/m0/s1
CAS number: 17510-99-5
IUPAC Name:3-deoxy-D-erythro-hex-2-ulosonate
Traditional IUPAC Name: (4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid
SMILES:C(=O)([O-])C(=O)CC(O)C(O)CO
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassKeto acids and derivatives
Direct Parent Medium-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 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 Solubility134.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.32 m3·mol-1ChemAxon
Polarizability15.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
2-dehydro-3-deoxy-D-gluconate + ATP → Hydrogen ion + 2-dehydro-3-deoxy-D-gluconate 6-phosphate + ADP
(4S,5S)-4,5-dihydroxy-2,6-dioxohexanoate + Hydrogen ion + NADH-P-OR-NOP → 2-dehydro-3-deoxy-D-gluconate + NAD-P-OR-NOP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
References
References:
  • Kim S, Lee SB (2006)Characterization of Sulfolobus solfataricus 2-keto-3-deoxy-D-gluconate kinase in the modified Entner-Doudoroff pathway. Bioscience, biotechnology, and biochemistry 70, Pubmed: 16794308
Synthesis Reference: Plantier-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
External Links:
ResourceLink
HMDBHMDB01353
BIGG34249
PUBCHEM44229111
CHEBI57990
LIGAND-CPDC00204
CAS17510-99-5