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Identification
YMDB IDYMDB00442
Name2-Isopropylmaleic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Isopropylmaleic acid is an intermediate in the leucine biosynthesis pathway. In yeast, it is an aluminium binding substance. [Biocyc LEUSYN-PWY]
Structure
Thumb
Synonyms
  • 2-Isopropylmaleate
  • 2-isopropylmaleic acid
  • beta-Isopropylmaleate
  • Isopropylmaleic acid
  • b-Isopropylmaleate
  • b-Isopropylmaleic acid
  • beta-Isopropylmaleic acid
  • β-isopropylmaleate
  • β-isopropylmaleic acid
CAS numberNot Available
WeightAverage: 158.1519
Monoisotopic: 158.057908808
InChI KeyNJMGRJLQRLFQQX-HYXAFXHYSA-N
InChIInChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-
IUPAC Name(2Z)-2-(propan-2-yl)but-2-enedioic acid
Traditional IUPAC Name2-isopropylmaleic acid
Chemical FormulaC7H10O4
SMILESCC(C)C(=C\C(O)=O)\C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.64 g/LALOGPS
logP1.05ALOGPS
logP1.09ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.11 m³·mol⁻¹ChemAxon
Polarizability15.11 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Leucine BiosynthesisPW002475 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
SMPDB Reactions
2-Isopropylmalic acidwater + 2-Isopropylmaleic acid
2-Isopropylmaleic acid + water3-Isopropylmalate
KEGG Reactions
water + 2-Isopropylmaleic acid2-Isopropylmalic acid
3-Isopropylmalatewater + 2-Isopropylmaleic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Suzuki, T., Tamura, S., Nakanishi, H., Tashiro, M., Nishizawa, N. K., Yoshimura, E. (2007). "Reduction of aluminum toxicity by 2-isopropylmalic acid in the budding yeast Saccharomyces cerevisiae." Biol Trace Elem Res 120:257-263.17916978
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17275
HMDB IDHMDB0012241
Pubchem Compound ID21954611
Kegg IDC02631
ChemSpider ID4444164
FOODB IDFDB028883
Wikipedia IDNot Available
BioCyc IDNot Available

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:
LEU1
Uniprot ID:
P07264
Molecular weight:
85793.70313
Reactions
(2R,3S)-3-isopropylmalate → (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O → (2S)-2-isopropylmalate.