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Record Information
Version3.6
Creation Date2009-04-06 16:21:36 UTC
Update Date2017-03-02 21:32:23 UTC
HMDB IDHMDB12241
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsopropylmaleate
DescriptionIsopropylmaleate is found in the leucine biosynthesis pathway. 2-Isopropylmalate reversibly breaks down to form isopropylmaleate and H2O. The reaction is catalyzed by 3-isopropylmalate dehydratase.
Structure
Thumb
Synonyms
ValueSource
2-IsopropylmaleateChEBI
beta-IsopropylmaleateChEBI
2-Isopropylmaleic acidGenerator
Isopropylmaleic acidGenerator
b-IsopropylmaleateGenerator
b-Isopropylmaleic acidGenerator
beta-Isopropylmaleic acidGenerator
β-isopropylmaleateGenerator
β-isopropylmaleic acidGenerator
Chemical FormulaC7H10O4
Average Molecular Weight158.1519
Monoisotopic Molecular Weight158.057908808
IUPAC Name(2Z)-2-(propan-2-yl)but-2-enedioic acid
Traditional Name2-isopropylmaleic acid
CAS Registry NumberNot Available
SMILES
CC(C)C(=C\C(O)=O)\C(O)=O
InChI Identifier
InChI=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-
InChI KeyNJMGRJLQRLFQQX-HYXAFXHYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.64 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.11 m3·mol-1ChemAxon
Polarizability15.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-45d74194c5fbfea04a10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-7900000000-7e85e22040474be6339cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9100000000-672bc73595a1f6b84201View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1900000000-48b9e2f85f15343470aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-090a-5900000000-5c4991c8530e2f8a6edaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-9400000000-0d37fa6e2313dc5f09a3View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028883
KNApSAcK IDNot Available
Chemspider ID4444164
KEGG Compound IDC02631
BioCyc IDCPD-9451
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12241
Metagene LinkHMDB12241
METLIN IDNot Available
PubChem Compound5280533
PDB IDNot Available
ChEBI ID17275
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available