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Identification
ECMDB IDECMDB04158
Name3-Isopropylmalate
Description3-Isopropylmalate is an intermediate in valine, leucine and isoleucine biosynthesis. It is a substrate for 3-isopropylmalate dehydrogenase (TT_C0867)
Structure
Thumb
Synonyms
  • β-isopropylmalate
  • (2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioate
  • (2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
  • (2R,3S)-2-hydroxy-3-isopropylsuccinate
  • (2R,3S)-2-hydroxy-3-isopropylsuccinic acid
  • (2R,3S)-3-carboxy-2-hydroxy-4-methylpentanoate
  • (2R,3S)-3-carboxy-2-hydroxy-4-methylpentanoic acid
  • (2R,3S)-3-Isopropylmalate
  • (2R,3S)-3-isopropylmalic acid
  • 2-D-Threo-Hydroxy-3-carboxy-isocaproate
  • 2-D-Threo-Hydroxy-3-carboxy-isocaproic acid
  • 2-D-Threo-hydroxy-3-carboxyisocaproate
  • 2-D-Threo-hydroxy-3-carboxyisocaproic acid
  • 3-3-Isopropylmalate
  • 3-3-Isopropylmalic acid
  • 3-Carboxy-2-hydroxy-4-methylpentanoate
  • 3-Carboxy-2-hydroxy-4-methylpentanoic acid
  • 3-isopropylmalate
  • 3-Isopropylmalic acid
  • 3IPMA
  • Beta-Isopropylmalate
  • Beta-Isopropylmalic acid
  • IPM
CAS number921-28-8
WeightAverage: 176.1672
Monoisotopic: 176.068473494
InChI KeyInChIKey=RNQHMTFBUSSBJQ-CRCLSJGQSA-N
InChIInChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)/t4-,5+/m0/s1
IUPAC Name(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
Traditional IUPAC Name(2R,3S)-2-hydroxy-3-isopropylbutanedioic acid
Chemical FormulaC7H12O5
SMILES[H][C@](O)(C(O)=O)[C@]([H])(C(C)C)C(O)=O
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassDicarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Alpha Hydroxy Acids and Derivatives
  • Short-chain Hydroxy Acids and Derivatives
  • Beta Hydroxy Acids and Derivatives
  • 3-isopropylmalic acid(ChEBI)
  • Branched Fatty Acids
Substituents
  • Aliphatic Acyclic Compounds
  • Alpha Hydroxy Acids and Derivatives
  • Short-chain Hydroxy Acids and Derivatives
  • Beta Hydroxy Acids and Derivatives
  • 3-isopropylmalic acid(ChEBI)
  • Branched Fatty Acids
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility83.3ALOGPS
logP0.28ALOGPS
logP0.16ChemAxon
logS-0.33ALOGPS
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.6 m3·mol-1ChemAxon
Polarizability16.47 Å3ChemAxon
Biological Properties
Cellular Locations
  • Outer membrane
  • Inner membrane
Pathways
  • Valine, leucine and isoleucine biosynthesis ‐ ec00290
Ecocyc Pathways
Concentrations
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureCitationComment
Details describing the conversion of literature concentrations can be found here.
Spectra
SpectraNot Available
References
References:
  • 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-D590.21097882
  • 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-D114.22080510
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID:35114
HMDB ID:HMDB12156
Pubchem Compound ID:5462261
Kegg ID:C04411
ChemSpider ID:4575349
BioCyc ID:2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE
EcoCyc ID:2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE
Ligand Expo:IPM

Enzymes

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:
49881.5
Reactions
(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the oxidation of 3-carboxy-2-hydroxy-4- methylpentanoate (3-isopropylmalate) to 3-carboxy-4-methyl-2- oxopentanoate. The product decarboxylates to 4-methyl-2 oxopentanoate
Gene Name:
leuB
Uniprot ID:
P30125
Molecular weight:
39516.6
Reactions
(2R,3S)-3-isopropylmalate + NAD(+) = 4-methyl-2-oxopentanoate + CO(2) + NADH.
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:
22487.3
Reactions
(2R,3S)-3-isopropylmalate = (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O = (2S)-2-isopropylmalate.