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Record Information
Version3.6
Creation Date2009-04-06 16:20:09 UTC
Update Date2017-09-14 03:35:31 UTC
HMDB IDHMDB0012156
Secondary Accession Numbers
  • HMDB12156
Metabolite Identification
Common Name3-Isopropylmalate
Description3-Isopropylmalate is an intermediate in valine, leucine and isoleucine biosynthesis. It is a substrate for 3-isopropylmalate dehydrogenase (TT_C0867) and can be generated from the reduction of 2-isopropyl-3-oxosuccinate. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity, Branched-chain amino acid transferase (IlvE) and Tyrosine aminotransferase (TyrB). This pathway is part of the superpathway of leucine, valine, and isoleucine biosynthesis, that generates not only isoleucine and valine, but also leucine.
Structure
Thumb
Synonyms
ValueSource
(2R,3S)-2-Hydroxy-3-isopropylsuccinic acidChEBI
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoic acidChEBI
2-D-threo-Hydroxy-3-carboxy-isocaproateChEBI
2-D-threo-Hydroxy-3-carboxyisocaproic acidChEBI
3-Carboxy-2-hydroxy-4-methylpentanoateChEBI
(2R,3S)-2-Hydroxy-3-isopropylsuccinateGenerator
3-Isopropylmalic acidGenerator
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoateGenerator
2-D-threo-Hydroxy-3-carboxy-isocaproic acidGenerator
2-D-threo-Hydroxy-3-carboxyisocaproateGenerator
3-Carboxy-2-hydroxy-4-methylpentanoic acidGenerator
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioateHMDB
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioic acidHMDB
(2R,3S)-3-IsopropylmalateHMDB
(2R,3S)-3-Isopropylmalic acidHMDB
3-3-Isopropylmalic acidHMDB
IPMHMDB
beta-Isopropylmalate, erythro-(L)-isomerMeSH
beta-IsopropylmalateMeSH
Chemical FormulaC7H12O5
Average Molecular Weight176.1672
Monoisotopic Molecular Weight176.068473494
IUPAC Name(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
Traditional Name(2R,3S)-3-isopropylmalic acid
CAS Registry Number921-28-8
SMILES
CC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O
InChI Identifier
InChI=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
InChI KeyRNQHMTFBUSSBJQ-CRCLSJGQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility83.3 mg/mLALOGPS
logP0.28ALOGPS
logP0.16ChemAxon
logS-0.33ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.6 m3·mol-1ChemAxon
Polarizability16.47 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
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0920000000-4ec856cc4eb69ab95cccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-1900000000-224a91a676e183e74333View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06sl-7900000000-b06817c1e6edcae6d425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9300000000-479bb2145817abc0bf1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1900000000-acde792ba60cae65a216View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0far-9700000000-cf8f9dd2b32cfd503f42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9100000000-138111afc561c6d0a2ecView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
No entries found
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 IDFDB028813
KNApSAcK IDNot Available
Chemspider ID4575349
KEGG Compound IDC04411
BioCyc ID2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0012156
METLIN IDNot Available
PubChem Compound5462261
PDB IDIPM
ChEBI ID35114
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available