3-Isopropylmalate (PAMDB000641)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000641
Identification
Name: 3-Isopropylmalate
Description:3-Isopropylmalate is an intermediate in valine, leucine and isoleucine biosynthesis. It is a substrate for 3-isopropylmalate dehydrogenase (TT_C0867)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • β-isopropylmalate
  • β-isopropylmalic acid
  • (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
  • b-Isopropylmalate
  • b-Isopropylmalic acid
  • Beta-Isopropylmalate
  • Beta-Isopropylmalic acid
  • IPM
  • β-Isopropylmalate
  • β-Isopropylmalic acid
Chemical Formula: C7H12O5
Average Molecular Weight: 176.1672
Monoisotopic Molecular Weight: 176.068473494
InChI Key: RNQHMTFBUSSBJQ-CRCLSJGQSA-N
InChI: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
CAS number: 921-28-8
IUPAC Name:(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
Traditional IUPAC Name: (2R,3S)-3-isopropylmalic acid
SMILES:CC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Branched fatty acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
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
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
3-Isopropylmalate <> Isopropylmaleate + Water
3-Isopropylmalate + NAD <> 2-Isopropyl-3-oxosuccinate + NADH + Hydrogen ion
3-Isopropylmalate + NAD > Ketoleucine + Carbon dioxide + NADH
3-Isopropylmalate + Isopropylmaleate + Water <> 2-Isopropylmalic acid
3-Isopropylmalate + NAD + 2-Isopropyl-3-oxosuccinate <> Ketoleucine + Carbon dioxide + NADH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID35114
HMDB IDHMDB12156
Pubchem Compound ID5462261
Kegg IDC04411
ChemSpider ID4575349
Wikipedia IDNot Available
BioCyc ID2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE
EcoCyc ID2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE
Ligand ExpoIPM