3-Carboxy-3-hydroxy-isocaproate (PAMDB000567)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000567
Identification
Name: 3-Carboxy-3-hydroxy-isocaproate
Description:3-carboxy-3-hydroxy-isocaproate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. Alpha isopropylmalate is involved in the biosynthesis of leucine. The protein product of MJ0720 was found to be alpha-isopropylmalate dehydrogenase (LeuB) and was found to catalyze the NAD-dependent decarboxylation of one isomer of DL-threo-isopropylmalate to 2-ketoisocaproate; thus, it is involved in the biosynthesis of leucine. (PMID 10940051)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-isopropylmalate
  • α-isopropylmalic acid
  • (2S)-2-isopropylmalate
  • (2S)-2-isopropylmalic acid
  • 2IPMA
  • 3-Carboxy-3-hydroxy-4-methylpentanoate
  • 3-Carboxy-3-hydroxy-4-methylpentanoic acid
  • 3-carboxy-3-hydroxy-isocaproate
  • 3-Carboxy-3-hydroxy-isocaproic acid
  • 3-Hydroxy-4-methyl-3-carboxypentanoate
  • 3-Hydroxy-4-methyl-3-carboxypentanoic acid
  • a-Isopropylmalate
  • a-Isopropylmalic acid
  • Alpha-Isopropylmalate
  • Alpha-Isopropylmalic acid
  • α-Isopropylmalate
  • α-Isopropylmalic acid
Chemical Formula: C7H10O5
Average Molecular Weight: 174.1513
Monoisotopic Molecular Weight: 174.05282343
InChI Key: BITYXLXUCSKTJS-UHFFFAOYSA-L
InChI:InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/p-2
CAS number: Not Available
IUPAC Name:2-hydroxy-2-(propan-2-yl)butanedioate
Traditional IUPAC Name: 2-isopropylmalate
SMILES:CC(C)C(O)(CC([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
  • Branched fatty acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Carboxylic acid salt
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility41.3 mg/mLALOGPS
logP-0.1ALOGPS
logP0.21ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area100.49 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.26 m3·mol-1ChemAxon
Polarizability15.49 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
alpha-Ketoisovaleric acid + Acetyl-CoA + Water > Hydrogen ion + 3-Carboxy-3-hydroxy-isocaproate + Coenzyme A
3-Carboxy-3-hydroxy-isocaproate <> Isopropylmaleate + Water
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-05d12fb256c35fe44030View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ow-8900000000-87fc335f95e2e5d7706cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-7900000000-6d742aea834098a47a78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-4900000000-572b60751e5d80bdeafbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-9600000000-bff27fb29bfce1df6dbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9100000000-438c2f1f71f400371db5View in MoNA
References
References:
  • Howell, D. M., Graupner, M., Xu, H., White, R. H. (2000). "Identification of enzymes homologous to isocitrate dehydrogenase that are involved in coenzyme B and leucine biosynthesis in methanoarchaea." J Bacteriol 182:5013-5016. Pubmed: 10940051
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID35129
HMDB IDNot Available
Pubchem Compound ID6419726
Kegg IDC02504
ChemSpider ID4925359
Wikipedia IDNot Available
BioCyc ID3-CARBOXY-3-HYDROXY-ISOCAPROATE
EcoCyc ID3-CARBOXY-3-HYDROXY-ISOCAPROATE