Record Information
Version2.0
Creation Date2012-05-31 14:24:18 -0600
Update Date2015-06-03 17:19:11 -0600
Secondary Accession Numbers
  • ECMDB20040
Identification
Name:2-Dehydro-3-deoxy-D-glucarate
Description2-dehydro-3-deoxy-D-glucarate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. It is a substrate for 2-dehydro-3-deoxyglucarate aldolase (EC 4.1.2.20) which is an enzyme that catalyzes the chemical reaction: 2-dehydro-3-deoxy-D-glucarate = pyruvate + tartronate semialdehyde
Structure
Thumb
Synonyms:
  • 2-Dehydro-3-deoxy-D-glucarate
  • 2-Dehydro-3-deoxy-D-glucaric acid
  • 2-Keto-3-deoxy-D-glucarate
  • 2-Keto-3-deoxy-D-glucaric acid
  • 2-Keto-3-deoxy-glucarate
  • 2-Keto-3-deoxy-glucaric acid
  • 3-Deoxy-D-erythro-hex-2-ulosarate
  • 3-Deoxy-D-erythro-hex-2-ulosaric acid
  • KGR
Chemical Formula:C6H8O7
Weight:Average: 192.1235
Monoisotopic: 192.02700261
InChI Key:QUURPCHWPQNNGL-OKKQSCSOSA-N
InChI:InChI=1S/C6H8O7/c7-2(4(9)6(12)13)1-3(8)5(10)11/h2,4,7,9H,1H2,(H,10,11)(H,12,13)/t2-,4-/m0/s1
CAS number:Not Available
IUPAC Name:(2S,3S)-2,3-dihydroxy-5-oxohexanedioic acid
Traditional IUPAC Name:2-dehydro-3-deoxy-D-glucarate
SMILES:[H][C@](O)(CC(=O)C(O)=O)[C@]([H])(O)C(O)=O
Chemical Taxonomy
Description 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
  • Beta-hydroxy acid
  • Alpha-hydroxy acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • 1,2-diol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility52.7 g/LALOGPS
logP-1.2ALOGPS
logP-1.5ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)2.5ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.18 m³·mol⁻¹ChemAxon
Polarizability15.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
superpathway of D-glucarate and D-galactarate degradationPW000795 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-dc22098bdfbe7bf4390dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-3900000000-d866ef19e96da0564480View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9400000000-a4c21560ef2a755924c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006w-2900000000-670ae8cd92a88762c2afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fg2-7900000000-1e841b13a298bc87f638View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9800000000-3d471b650b26cf2a0f96View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17305
HMDB IDNot Available
Pubchem Compound ID440165
Kegg IDC03921
ChemSpider ID389156
Wikipedia IDNot Available
BioCyc ID2-KETO-3-DEOXY-D-GLUCARATE
EcoCyc ID2-KETO-3-DEOXY-D-GLUCARATE

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the dehydration of glucarate to 5-keto-4- deoxy-D-glucarate (5-kdGluc). Also acts on L-idarate
Gene Name:
gudD
Uniprot ID:
P0AES2
Molecular weight:
49141
Reactions
D-glucarate = 5-dehydro-4-deoxy-D-glucarate + H(2)O.
General function:
Involved in carbon-carbon lyase activity
Specific function:
Catalyzes the reversible retro-aldol cleavage of both 5- keto-4-deoxy-D-glucarate and 2-keto-3-deoxy-D-glucarate to pyruvate and tartronic semialdehyde
Gene Name:
garL
Uniprot ID:
P23522
Molecular weight:
27384
Reactions
5-dehydro-4-deoxy-D-glucarate = pyruvate + tartronate semialdehyde.
2-dehydro-3-deoxy-D-glucarate = pyruvate + tartronate semialdehyde.