Record Information
Version2.0
Creation Date2012-05-31 10:26:56 -0600
Update Date2015-09-13 12:56:08 -0600
Secondary Accession Numbers
  • ECMDB00491
Identification
Name:3-Methyl-2-oxovaleric acid
Description3-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
  • 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
  • 2K3MVA
  • 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
  • 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:C6H10O3
Weight:Average: 130.1418
Monoisotopic: 130.062994186
InChI Key:JVQYSWDUAOAHFM-UHFFFAOYSA-N
InChI:InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
CAS number:1460-34-0
IUPAC Name:3-methyl-2-oxopentanoic acid
Traditional IUPAC Name:3-methyl-2-oxopentanoic acid
SMILES:CCC(C)C(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:915.5 mg/mL [sodium salt, HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.86 g/LALOGPS
logP1ALOGPS
logP1.75ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.79 m³·mol⁻¹ChemAxon
Polarizability13.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Leucine BiosynthesisPW000811 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolite: Leucine biosynthesisPW000980 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvatePW000978 ThumbThumb?image type=greyscaleThumb?image type=simple
isoleucine biosynthesisPW000818 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Valine, leucine and isoleucine biosynthesis ec00290
  • Valine, leucine and isoleucine degradation ec00280
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-000i-9610000000-d2ffd4c2796688c555eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-000i-9720000000-9cbc934e100bedd87f17View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-9720000000-5acbdc73aee24c023763View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-6930000000-8c2cf1d8df538010611bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-6930000000-7bef6751c4c607393e5eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0hg9-4950000000-3e1c700a6f553bf63afbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9610000000-d2ffd4c2796688c555eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9720000000-9cbc934e100bedd87f17View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9720000000-5acbdc73aee24c023763View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-6930000000-8c2cf1d8df538010611bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-d08073312b337cdae9e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05bo-9400000000-9937bff65302162dc3b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000w-9300000000-0a6ff60455403c38be39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9000000000-7ee6d2fb63c6ea4cccfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002b-9000000000-47d18dff23b741029581View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-ae9da2a9acfa56fc6091View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004r-5900000000-a3f740a5c859439255beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06sr-7900000000-4920c1aefcca814ec1f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-16995fa8eb603d828a2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a6ccc899039a438533aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-5900000000-50107933abbe9c175553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-9700000000-23998218af9ee2898594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a30461e2df45eeb8f795View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
  • Przyrembel H, Bremer HJ, Duran M, Bruinvis L, Ketting D, Wadman SK, Baumgartner R, Irle U, Bachmann C: Propionyl-CoA carboxylase deficiency with overflow of metabolites of isoleucine catabolism at all levels. Eur J Pediatr. 1979 Jan 18;130(1):1-14. Pubmed: 759179
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Wendel U, Even G, Langenbeck U, Schadewaldt P, Hummel W: Determination of (S)- and (R)-2-oxo-3-methylvaleric acid in plasma of patients with maple syrup urine disease. Clin Chim Acta. 1992 Jun 15;208(1-2):85-91. Pubmed: 1638756
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Kondo, Shigeo; Sudo, Tetsuji; Ogiwara, Mitsuo; Takeuchi, Hiroshi. a-Oxo-b-methyl-n-valeric acid and its salts. Jpn. Kokai Tokkyo Koho (1979), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15614
HMDB IDHMDB00491
Pubchem Compound ID439286
Kegg IDC03465
ChemSpider ID46
Wikipedia IDNot Available
BioCyc ID2-KETO-3-METHYL-VALERATE
EcoCyc ID2-KETO-3-METHYL-VALERATE

Enzymes

General function:
Involved in metabolic process
Specific function:
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2- oxobutanoate + H(2)O
Gene Name:
ilvD
Uniprot ID:
P05791
Molecular weight:
65531
Reactions
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2-oxobutanoate + H(2)O.
General function:
Involved in 2-isopropylmalate synthase activity
Specific function:
Catalyzes the condensation of the acetyl group of acetyl-CoA with 3-methyl-2-oxobutanoate (2-oxoisovalerate) to form 3-carboxy-3-hydroxy-4-methylpentanoate (2-isopropylmalate)
Gene Name:
leuA
Uniprot ID:
P09151
Molecular weight:
57297
Reactions
Acetyl-CoA + 3-methyl-2-oxobutanoate + H(2)O = (2S)-2-isopropylmalate + CoA.
General function:
Involved in catalytic activity
Specific function:
Acts on leucine, isoleucine and valine
Gene Name:
ilvE
Uniprot ID:
P0AB80
Molecular weight:
34093
Reactions
L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate.
L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate.
L-valine + 2-oxoglutarate = 3-methyl-2-oxobutanoate + L-glutamate.