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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:02 UTC
Update Date2020-03-11 16:00:37 UTC
HMDB IDHMDB0012149
Secondary Accession Numbers
  • HMDB12149
Metabolite Identification
Common Name2-Isopropyl-3-oxosuccinate
Description2-Isopropyl-3-oxosuccinate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain that contains less than 6 carbon atoms. 2-Isopropyl-3-oxosuccinate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Isopropyl-3-oxosuccinate exists in all living species, ranging from bacteria to humans. 2-Isopropyl-3-oxosuccinate has been detected, but not quantified in, several different foods, such as garden onion (var.), German camomiles, limes, cloud ear fungus, and citrus. This could make 2-isopropyl-3-oxosuccinate a potential biomarker for the consumption of these foods. 2-Isopropyl-3-oxosuccinate is an intermediate in leucine biosynthesis and can be generated from (2R,3S)-3-isopropylmalate. It is the third step in leucine biosynthesis after the fork from valine synthesis. It is an oxidative decarboxylation. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity: branched-chain amino acid transferase (IlvE) and tyrosine aminotransferase (TyrB). In this pathway, 2-isopropyl-3-oxosuccinate is converted into 4-methyl-2-oxopentanoate via a spontaneous reaction (BioCyc).
Structure
Data?1583942437
Synonyms
ValueSource
(2S)-2-(1-Methylethyl)-3-oxobutanedioic acidChEBI
(2S)-2-Isopropyl-3-oxosuccinateChEBI
3-Carboxy-4-methyl-2-oxopentanoateChEBI
2-oxo-4-Methyl-3-carboxypentanoateKegg
(2S)-2-(1-Methylethyl)-3-oxobutanedioateGenerator
(2S)-2-Isopropyl-3-oxosuccinic acidGenerator
3-Carboxy-4-methyl-2-oxopentanoic acidGenerator
2-oxo-4-Methyl-3-carboxypentanoic acidGenerator
2-Isopropyl-3-oxosuccinic acidGenerator
(2S)-3-oxo-2-(Propan-2-yl)butanedioateHMDB
(2S)-3-oxo-2-(Propan-2-yl)butanedioic acidHMDB
2-(1-Methylethyl)-3-oxobutanedioic acidHMDB
2-Oxo-3-isopropylsuccinic acidHMDB
Chemical FormulaC7H10O5
Average Molecular Weight174.1513
Monoisotopic Molecular Weight174.05282343
IUPAC Name(3S)-2-oxo-3-(propan-2-yl)butanedioic acid
Traditional Name(2S)-2-isopropyl-3-oxobutanedioic acid
CAS Registry Number1245945-28-1
SMILES
CC(C)[C@H](C(O)=O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyHIIZAGQWABAMRR-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Branched fatty acid
  • Short-chain keto acid
  • Methyl-branched fatty acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

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 Solubility7.02 g/LALOGPS
logP0.43ALOGPS
logP1.23ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-10ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.06 m³·mol⁻¹ChemAxon
Polarizability15.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-a431ad34a78f0adc25afSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0g74-9331000000-f234980692c6ed06a94eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-acd1ea66574d55eb331dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06v0-5900000000-7e737232c4fb38bff3bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9600000000-844c8da366f084302d2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-1900000000-bdd65fc36b7ec2c68915Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-7900000000-31ff420a87e647dd1154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9100000000-ffbf76307b5afc43379bSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot 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
FooDB IDFDB030114
KNApSAcK IDNot Available
Chemspider ID4575347
KEGG Compound IDC04236
BioCyc IDCPD-7100
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462259
PDB IDNot Available
ChEBI ID1467
Food Biomarker OntologyNot Available
VMH ID3C4MOP
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available