Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


5-Dehydro-4-deoxy-D-glucuronate (M2MDB000951)

Record Information
Version2.0
Creation Date2012-05-31 14:27:38 -0600
Update Date2015-06-03 17:19:19 -0600
Secondary Accession Numbers
  • ECMDB20103
Identification
Name:5-Dehydro-4-deoxy-D-glucuronate
Description5-dehydro-4-deoxy-D-glucuronate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (4S,5R)-4,5-dihydroxy-2,6-dioxohexanoate
  • (4S,5R)-4,5-Dihydroxy-2,6-dioxohexanoic acid
  • 4,5-dihydroxy-2,6-dioxo-hexanoate
  • 4,5-Dihydroxy-2,6-dioxo-hexanoic acid
  • 4-Deoxy-5-ketouronate
  • 4-deoxy-5-ketouronic acid
  • 4-Deoxy-L-threo-5-hexosulose uronate
  • 4-Deoxy-L-threo-5-hexosulose uronic acid
  • 5-Dehydro-4-deoxy-D-glucuronic acid
  • 5-keto-4-deoxyuronate
  • 5-keto-4-Deoxyuronic acid
  • DKI
Chemical Formula:C6H8O6
Weight:Average: 176.1241
Monoisotopic: 176.032087988
InChI Key:IMUGYKFHMJLTOU-UCORVYFPSA-N
InChI:InChI=1S/C6H8O6/c7-2-5(10)3(8)1-4(9)6(11)12/h2-3,5,8,10H,1H2,(H,11,12)/t3-,5-/m0/s1
CAS number:Not Available
IUPAC Name:(4S,5R)-4,5-dihydroxy-2,6-dioxohexanoic acid
Traditional IUPAC Name:(4S,5R)-4,5-dihydroxy-2,6-dioxohexanoic acid
SMILES:[H][C@](O)(CC(=O)C(O)=O)[C@@]([H])(O)C=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
  • Alpha-keto acid
  • Beta-hydroxy aldehyde
  • Monosaccharide
  • Beta-hydroxy ketone
  • Alpha-hydroxy ketone
  • Alpha-hydroxyaldehyde
  • 1,2-diol
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility59.5 g/LALOGPS
logP-0.83ALOGPS
logP-1.6ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.26 m³·mol⁻¹ChemAxon
Polarizability14.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
5-Dehydro-4-deoxy-D-glucuronate <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate
5-Dehydro-4-deoxy-D-glucuronate > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate
SMPDB Pathways:
Collection of Reactions without pathwaysPW001891 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1900000000-a9f87e1e1b45b21a9c50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-6900000000-29c988b39df0688cac74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g3-9200000000-1928f891d89be4d0a031View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-4900000000-d0ab666bff7db4170c90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9400000000-298be5aa2cd24e61771eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pic-9200000000-1ba33abdcb4a9282b198View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17117
HMDB IDNot Available
Pubchem Compound ID440207
Kegg IDC04053
ChemSpider ID389194
Wikipedia IDNot Available
BioCyc IDCPD-37
EcoCyc IDCPD-37
Ligand ExpoD54

Enzymes

Protein Details
1. 4-deoxy-L-threo-5-hexosulose-uronate ketol-isomerase
General function:
Involved in 4-deoxy-L-threo-5-hexosulose-uronate ketol-isomerase activity
Specific function:
4-deoxy-L-threo-5-hexosulose uronate = 3- deoxy-D-glycero-2,5-hexodiulosonate
Gene Name:
kduI
Uniprot ID:
Q46938
Molecular weight:
31076
Reactions
4-deoxy-L-threo-5-hexosulose uronate = 3-deoxy-D-glycero-2,5-hexodiulosonate.