Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000605
Identification
Name: 2-Keto-3-methyl-valerate
Description:3-Methyl-2-oxovaleric acid is a metabolite of isoleucine in man, animals and bacteria. It is the alpha-keto acid analogue of isoleucine. 3-Methyl-2-oxovaleric acid is produced from isoleucine by cytosolic branched chain aminotransferase 1 (EC:2.6.1.42), whereupon it is further degraded by branched chain keto acid dehydrogenase E1 to 2-Methyl-1-hydroxybutyl-ThPP.
Structure
Thumb
Synonyms:
  • α-keto-β-methyl-valerate
  • α-keto-β-methyl-valeric acid
  • α-keto-methylvalerate
  • α-keto-methylvaleric acid
  • (3S)-3-Methyl-2-oxopentanoate
  • (3R)-3-Methyl-2-oxopentanoate
  • (3R)-3-Methyl-2-oxopentanoic acid
  • (3S)-3-methyl-2-oxopentanoate
  • (3S)-3-methyl-2-oxopentanoic acid
  • (S)-2-oxo-3-methylpentanoate
  • (S)-3-methyl-2-oxopentanoate
  • (R)-3-methyl-2-oxopentanoate
  • (R)-3-methyl-2-oxopentanoic acid
  • (S)-2-oxo-3-methylpentanoate
  • (S)-2-oxo-3-methylpentanoic acid
  • (S)-3-methyl-2-oxopentanoate
  • (S)-3-methyl-2-oxopentanoic acid
  • (S)-3-methyl-2-oxovalerate
  • (S)-3-methyl-2-oxovaleric acid
  • 2-keto-3-methyl-valerate
  • 2-Keto-3-methyl-valeric acid
  • 2-keto-3-methylvalerate
  • 2-keto-3-methylvaleric acid
  • 2-Oxo-3-methyl-N-valerate
  • 2-Oxo-3-methyl-N-valeric acid
  • 2-Oxo-3-methylpentanoate
  • 2-Oxo-3-methylpentanoic acid
  • 2-Oxo-3-methylvalerate
  • 2-Oxo-3-methylvaleric acid
  • 2-Oxoisoleucine
  • 2-Oxokolavenate
  • 2-Oxokolavenic acid
  • 3-Methyl-2-oxo-pentanoate
  • 3-Methyl-2-oxo-pentanoic acid
  • 3-Methyl-2-oxo-Valerate
  • 3-Methyl-2-oxo-Valeric acid
  • 3-Methyl-2-oxopentanoate
  • 3-Methyl-2-oxopentanoic acid
  • 3-Methyl-2-oxovalerate
  • 3-Methyl-2-oxovaleric
  • 3-Methyl-2-oxovaleric acid
  • A-Keto-b-methyl-N-valerate
  • A-Keto-b-methyl-N-valeric acid
  • a-keto-b-Methyl-valerate
  • a-keto-b-Methyl-valeric acid
  • A-Keto-b-methylvalerate
  • A-Keto-b-methylvaleric acid
  • a-keto-Methylvalerate
  • a-keto-Methylvaleric acid
  • A-Oxo-b-methyl-N-valerate
  • A-Oxo-b-methyl-N-valeric acid
  • A-Oxo-b-methylvalerate
  • A-Oxo-b-methylvaleric acid
  • Alpha-Keto-beta-methyl-N-valerate
  • Alpha-Keto-beta-methyl-N-valeric acid
  • Alpha-Keto-beta-methyl-valerate
  • Alpha-Keto-beta-methyl-valeric acid
  • Alpha-Keto-beta-methylvalerate
  • Alpha-Keto-beta-methylvaleric acid
  • Alpha-Keto-methylvalerate
  • Alpha-Keto-methylvaleric acid
  • Alpha-Oxo-beta-methyl-N-valerate
  • Alpha-Oxo-beta-methyl-N-valeric acid
  • Alpha-Oxo-beta-methylvalerate
  • Alpha-Oxo-beta-methylvaleric acid
  • α-keto-Methylvalerate
  • α-keto-Methylvaleric acid
  • α-keto-β-Methyl-N-valerate
  • α-keto-β-Methyl-N-valeric acid
  • α-keto-β-Methyl-valerate
  • α-keto-β-Methyl-valeric acid
  • α-keto-β-Methylvalerate
  • α-keto-β-Methylvaleric acid
  • α-oxo-β-Methyl-N-valerate
  • α-oxo-β-Methyl-N-valeric acid
  • α-oxo-β-Methylvalerate
  • α-oxo-β-Methylvaleric acid
Chemical Formula: C6H9O3
Average Molecular Weight: 129.1339
Monoisotopic Molecular Weight: 129.055169154
InChI Key: JVQYSWDUAOAHFM-BYPYZUCNSA-M
InChI:InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)/p-1/t4-/m0/s1
CAS number: 1460-34-0
IUPAC Name:(3S)-3-methyl-2-oxopentanoate
Traditional IUPAC Name: (S)-3-methyl-2-oxopentanoate
SMILES:CC[C@H](C)C(=O)C([O-])=O
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Methyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Keto acid
  • Alpha-keto acid
  • Ketone
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility12.5 mg/mLALOGPS
logP0.9ALOGPS
logP1.75ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.2 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.63 m3·mol-1ChemAxon
Polarizability12.57 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
  • Valine, leucine and isoleucine biosynthesis pae00290
  • Valine, leucine and isoleucine degradation pae00280
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-5620b4eae30516174873View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-d9053af6ae24b52d5826View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-db79bf299009a6887756View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-5900000000-b6e4bf6b61d36f9fd8f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-9400000000-6c5640ec288bdaaf640cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-6712db6d9ef51bd9e424View 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
  • 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 ID35146
HMDB IDHMDB00491
Pubchem Compound ID6857401
Kegg IDC00671
ChemSpider ID19951083
Wikipedia IDNot Available
BioCyc ID2-KETO-3-METHYL-VALERATE
EcoCyc ID2-KETO-3-METHYL-VALERATE