2-Isopropyl-3-oxosuccinate (PAMDB000823)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000823
Identification
Name: 2-Isopropyl-3-oxosuccinate
Description: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 to 4-Methyl-2-oxopentanoate via spontaneous reaction.(BioCyc)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-(1-methylethyl)-3-oxobutanedioate
  • (2S)-2-(1-methylethyl)-3-oxobutanedioic acid
  • (2S)-2-Isopropyl-3-oxosuccinate
  • (2S)-2-isopropyl-3-oxosuccinic acid
  • (2S)-3-oxo-2-(propan-2-yl)butanedioate
  • (2S)-3-oxo-2-(propan-2-yl)butanedioic acid
  • 2-isopropyl-3-oxosuccinate
  • 2-Isopropyl-3-oxosuccinic acid
  • 2-Oxo-4-methyl-3-carboxypentanoate
  • 2-Oxo-4-methyl-3-carboxypentanoic acid
  • 3-Carboxy-4-methyl-2-oxopentanoate
  • 3-Carboxy-4-methyl-2-oxopentanoic acid
Chemical Formula: C7H10O5
Average Molecular Weight: 174.1513
Monoisotopic Molecular Weight: 174.05282343
InChI Key: HIIZAGQWABAMRR-BYPYZUCNSA-N
InChI: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
CAS number: Not Available
IUPAC Name:(3S)-2-oxo-3-(propan-2-yl)butanedioic acid
Traditional IUPAC Name: (2S)-2-isopropyl-3-oxobutanedioic acid
SMILES:CC(C)[C@H](C(O)=O)C(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Keto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct Parent Short-chain keto acids and derivatives
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Branched fatty acid
  • Beta-keto acid
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Beta-hydroxy ketone
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
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
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2-Isopropyl-3-oxosuccinate + Hydrogen ion > Ketoleucine + Carbon dioxide
3-Isopropylmalate + NAD <> 2-Isopropyl-3-oxosuccinate + NADH + Hydrogen ion
3-Isopropylmalate + NAD + 2-Isopropyl-3-oxosuccinate <> Ketoleucine + Carbon dioxide + NADH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-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
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 ID1467
HMDB IDHMDB12149
Pubchem Compound ID5462259
Kegg IDC04236
ChemSpider ID4575347
Wikipedia IDNot Available
BioCyc IDCPD-7100
EcoCyc IDCPD-7100