3-Methyl-2-oxovaleric acid (ECMDB00491) (M2MDB000141)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (3)
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
MOLSDFPDBSMILESInChI
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:
alpha-Ketoglutarate + L-Isoleucine <> 3-Methyl-2-oxovaleric acid + L-Glutamate
(R) 2,3-Dihydroxy-3-methylvalerate > 3-Methyl-2-oxovaleric acid + Water
(R) 2,3-Dihydroxy-3-methylvalerate <> 3-Methyl-2-oxovaleric acid + Water
L-Isoleucine + Oxoglutaric acid <> 3-Methyl-2-oxovaleric acid + L-Glutamate
3-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-Valine
3-Methyl-2-oxovaleric acid + Water + Acetyl-CoA + 3-Methyl-2-oxovaleric acid > Coenzyme A + Hydrogen ion + 2-Isopropylmalic acid
3-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Isoleucine + L-Isoleucine
(R) 2,3-Dihydroxy-3-methylvalerate > Water + 3-Methyl-2-oxovaleric acid + 3-Methyl-2-oxovaleric acid
alpha-Ketoglutarate + L-Isoleucine <>3 3-Methyl-2-oxovaleric acid + L-Glutamate
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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

Protein Details
1. Dihydroxy-acid dehydratase
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.
Protein Details
2. 2-isopropylmalate synthase
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.
Protein Details
3. Branched-chain-amino-acid aminotransferase
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.