Record Information
Version2.0
Creation Date2012-05-31 10:26:35 -0600
Update Date2015-09-13 12:56:08 -0600
Secondary Accession Numbers
  • ECMDB00402
Identification
Name:2-Isopropylmalic acid
Description2-Isopropylmalic acid is involved in valine, leucine and isoleucine biosynthesis and pyruvate metabolism pathways. In pyruvate metabolism, 2-isopropylmalate synthase (EC:2.3.3.13) catalyzes the formation of 2-Isopropylmalic acid from acetyl-CoA. (KEGG)
Structure
Thumb
Synonyms:
  • (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
Weight:Average: 176.1672
Monoisotopic: 176.068473494
InChI Key:BITYXLXUCSKTJS-ZETCQYMHSA-N
InChI:InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1
CAS number:3237-44-3
IUPAC Name:(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional IUPAC Name:2-isopropyl-malic acid
SMILES:CC(C)[C@@](O)(CC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:144-146 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility181 g/LALOGPS
logP-0.29ALOGPS
logP0.21ChemAxon
logS0.01ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.58 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Leucine BiosynthesisPW000811 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolite: Leucine biosynthesisPW000980 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvatePW000978 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-1c869c73651e7e4e5ddaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00bl-9134000000-30fabfd0c26c38444fffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014r-6900000000-983e4a8edd0725d26979View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-016r-1900000000-5aa4d41c6ff31081d9d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-9200000000-d4b84f7b5f2a53ac5800View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-c680094e514a83eea978View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052o-9000000000-365c84abb7ec259fb43eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e28ea8cd657f96ff8357View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0690-1900000000-3b83300261e0daab2ef1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9700000000-2652db028b01706ac042View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9300000000-808bda4307e96bcfcc83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-2900000000-9fa33cd594a81b5d67cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-055r-9700000000-8ab90438d0e6c9b7d0beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9100000000-41e1c40b755f8bfaf000View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01x9-9800000000-53afadde706df1ef69abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4bfe3581b4b94540fea0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1470f6a6a1859e452712View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-9a718ee22b675ce18980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-8900000000-188b5287c7dbbce2559fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9000000000-2a93d25f081bcaa86a53View in MoNA
1D NMR1H 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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D 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
  • 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:
ResourceLink
CHEBI ID28635
HMDB IDHMDB00402
Pubchem Compound ID5280523
Kegg IDC02504
ChemSpider ID4444155
Wikipedia IDIsopropylmalic acid
BioCyc IDNot Available

Enzymes

General function:
Involved in 2-isopropylmalate synthase activity
Specific function:
Catalyzes the condensation of the acetyl group of acetyl-CoA with 3-methyl-2-oxobutanoate (2-oxoisovalerate) to form 3-carboxy-3-hydroxy-4-methylpentanoate (2-isopropylmalate)
Gene Name:
leuA
Uniprot ID:
P09151
Molecular weight:
57297
Reactions
Acetyl-CoA + 3-methyl-2-oxobutanoate + H(2)O = (2S)-2-isopropylmalate + CoA.
General function:
Involved in 3-isopropylmalate dehydratase activity
Specific function:
Catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate
Gene Name:
leuC
Uniprot ID:
P0A6A6
Molecular weight:
49882
Reactions
(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.
General function:
Involved in 3-isopropylmalate dehydratase activity
Specific function:
Catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate
Gene Name:
leuD
Uniprot ID:
P30126
Molecular weight:
22487
Reactions
(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.