Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000135
Name: 2-Isopropylmalic acid
Description:2-Isopropylmalic acid is involved in valine, leucine and isoleucine biosynthesis and pyruvate metabolism pathways. In pyruvate metabolism, 2-isopropylmalate synthase (EC: catalyzes the formation of 2-Isopropylmalic acid from acetyl-CoA. (KEGG)
  • (2S)-2-Isopropylmalate
  • (2S)-2-Isopropylmalic acid
  • 2-D-Threo-hydroxy-3-carboxy-isocaproate
  • 2-D-Threo-hydroxy-3-carboxy-isocaproic acid
  • 2-Hydroxy-2-isopropylsuccinate
  • 2-Hydroxy-2-isopropylsuccinic acid
  • 2-Isopropyl-2-hydroxybutanedioate
  • 2-Isopropyl-2-hydroxybutanedioic acid
  • 2-Isopropyl-Malate
  • 2-Isopropyl-Malic acid
  • 2-Isopropylmalate
  • 2-Isopropylmalic acid
  • 3-Carboxy-2-hydroxy-4-methylpentanoate
  • 3-Carboxy-2-hydroxy-4-methylpentanoic acid
  • 3-Carboxy-3-hydroxyisocaproate
  • 3-Carboxy-3-hydroxyisocaproic acid
  • 3-Isopropylmalate
  • 3-Isopropylmalic acid
  • A-Isopropylmalate
  • A-Isopropylmalic acid
  • Alpha-Isopropylmalate
  • Alpha-Isopropylmalic acid
  • b-Isopropylmalate
  • b-Isopropylmalic acid
  • Beta-Isopropylmalate
  • Beta-Isopropylmalic acid
  • α-Isopropylmalate
  • α-Isopropylmalic acid
  • β-Isopropylmalate
  • β-Isopropylmalic acid
Chemical Formula: C7H12O5
Average Molecular Weight: 176.1672
Monoisotopic Molecular Weight: 176.068473494
CAS number: 3237-44-3
IUPAC Name:(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional IUPAC Name: 2-isopropyl-malic acid
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Branched fatty acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: 144-146 °C
Experimental Properties:
Predicted Properties
Water Solubility181.0 mg/mLALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.58 m3·mol-1ChemAxon
Polarizability16.37 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0900000000-1bb48f5ddadbf88b8f6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00kr-9400000000-5df8f3f29d2e8a962cacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-05n0-9200000000-c62b1543d0e6a41388f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
  • 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
  • Pinkston D, Spiteller G, Von Henning H, Matthaei D: High resolution gas chromatography mass spectrometry of the methyl esters of organic acids from uremic hemofiltrates. J Chromatogr. 1981 Apr 10;223(1):1-19. Pubmed: 7251751
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Verhaeghe BJ, Van Bocxlaer JF, De Leenheer AP: Gas chromatographic/mass spectrometric identification of 3-hydroxydicarboxylic acids in urine. Biol Mass Spectrom. 1992 Jan;21(1):27-32. Pubmed: 1591279
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Schloss J V; Magolda R; Emptage M Synthesis of alpha-isopropylmalate, beta-isopropylmalate, and dimethylcitraconate. Methods in enzymology (1988), 166 92-6.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
Pubchem Compound ID5280523
Kegg IDC02504
ChemSpider ID4444155
Wikipedia IDNot Available
BioCyc IDNot Available