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4-Carboxy-4-hydroxy-2-oxoadipate (M2MDB000935)

Record Information
Version2.0
Creation Date2012-05-31 14:26:45 -0600
Update Date2015-06-03 17:19:17 -0600
Secondary Accession Numbers
  • ECMDB20087
Identification
Name:4-Carboxy-4-hydroxy-2-oxoadipate
Description4-carboxy-4-hydroxy-2-oxoadipate is a member of the chemical class known as Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • γ-oxalocitramalate
  • γ-oxalocitramalic acid
  • 2-Hydroxy-4-oxobutane-1,2,4-tricarboxylate
  • 2-Hydroxy-4-oxobutane-1,2,4-tricarboxylic acid
  • 4-Carboxy-4-hydroxy-2-ketoadipate
  • 4-Carboxy-4-hydroxy-2-ketoadipic acid
  • 4-carboxy-4-hydroxy-2-oxoadipate
  • 4-Carboxy-4-hydroxy-2-oxoadipic acid
  • 4-Hydroxy-4-acetyl-2-oxoglutarate
  • 4-Hydroxy-4-acetyl-2-oxoglutaric acid
  • 4-Hydroxy-4-carboxymethyl-2-oxoglutarate
  • 4-Hydroxy-4-carboxymethyl-2-oxoglutaric acid
  • 4-OH-4-ACETYL-2-OXOGLUTARATE
  • 4-OH-4-ACETYL-2-oxoglutaric acid
  • 4-oxalocitramalate
  • 4-Oxalocitramalic acid
Chemical Formula:C7H8O8
Weight:Average: 220.1336
Monoisotopic: 220.021917232
InChI Key:RQMCNDRMPZBEOD-UHFFFAOYSA-N
InChI:InChI=1S/C7H8O8/c8-3(5(11)12)1-7(15,6(13)14)2-4(9)10/h15H,1-2H2,(H,9,10)(H,11,12)(H,13,14)
CAS number:Not Available
IUPAC Name:2-hydroxy-4-oxobutane-1,2,4-tricarboxylic acid
Traditional IUPAC Name:2-hydroxy-4-oxobutane-1,2,4-tricarboxylic acid
SMILES:OC(=O)CC(O)(CC(=O)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Gamma-keto acid
  • Alpha-hydroxy acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Keto acid
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Ketone
  • Carboxylic acid
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility88.7 g/LALOGPS
logP-1.4ALOGPS
logP-1ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)2.4ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area149.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.97 m³·mol⁻¹ChemAxon
Polarizability17.46 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
4-Carboxy-4-hydroxy-2-oxoadipate <> 4-Carboxy-2-oxo-3-hexenedioate + Water
SMPDB Pathways:Not Available
KEGG Pathways:
  • Benzoate degradation via hydroxylation ec00362
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zi0-0950000000-15e3d1dcc4f96740195eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0900-4910000000-29ab897b82e9cced8dc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-5900000000-c246830c1a043e63bfbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-057i-0910000000-0981791de3884ec53b4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057r-3900000000-d628108f3495f6edbb78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9600000000-478b954e6e708fada733View 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 ID17250
HMDB IDNot Available
Pubchem Compound ID130
Kegg IDC04115
ChemSpider ID127
Wikipedia IDNot Available
BioCyc ID4-OH-4-ACETYL-2-OXOGLUTARATE
EcoCyc ID4-OH-4-ACETYL-2-OXOGLUTARATE

Enzymes

Protein Details
1. 2-keto-4-pentenoate hydratase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of 2-hydroxypentadienoic acid (enolic form of 2-oxopent-4-enoate) to 4-hydroxy-2-ketopentanoic acid
Gene Name:
mhpD
Uniprot ID:
P77608
Molecular weight:
28890
Reactions
4-hydroxy-2-oxopentanoate = 2-oxopent-4-enoate + H(2)O.