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Record Information
Version3.6
Creation Date2009-04-06 16:20:02 UTC
Update Date2017-08-16 07:59:27 UTC
HMDB IDHMDB0012149
Secondary Accession Numbers
  • HMDB12149
Metabolite Identification
Common Name2-Isopropyl-3-oxosuccinate
Description2-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 to 4-Methyl-2-oxopentanoate via spontaneous reaction.(BioCyc).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-(1-Methylethyl)-3-oxobutanedioic acidChEBI
(2S)-2-Isopropyl-3-oxosuccinateChEBI
3-Carboxy-4-methyl-2-oxopentanoateChEBI
(2S)-2-(1-Methylethyl)-3-oxobutanedioateGenerator
2-Isopropyl-3-oxosuccinic acidGenerator
(2S)-2-Isopropyl-3-oxosuccinic acidGenerator
3-Carboxy-4-methyl-2-oxopentanoic acidGenerator
(2S)-3-oxo-2-(Propan-2-yl)butanedioateHMDB
(2S)-3-oxo-2-(Propan-2-yl)butanedioic acidHMDB
2-oxo-4-Methyl-3-carboxypentanoateHMDB
2-oxo-4-Methyl-3-carboxypentanoic 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 NumberNot Available
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
DescriptionThis compound belongs to the class of chemical entities known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassKeto 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.06 m3·mol-1ChemAxon
Polarizability15.83 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-acd1ea66574d55eb331dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06v0-5900000000-7e737232c4fb38bff3bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9600000000-844c8da366f084302d2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-1900000000-bdd65fc36b7ec2c68915View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-7900000000-31ff420a87e647dd1154View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9100000000-ffbf76307b5afc43379bView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028806
KNApSAcK IDNot Available
Chemspider ID4575347
KEGG Compound IDC04236
BioCyc IDCPD-7100
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0012149
METLIN IDNot Available
PubChem Compound5462259
PDB IDNot Available
ChEBI ID1467
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available