Back to Compounds

Showing Compound 3-Methyl-2-oxopentanoic acid (FDB021447)

Record Information
Version1.0
Creation date2010-04-08 22:15:42 UTC
Update date2020-09-17 15:40:34 UTC
Primary IDFDB021447
Secondary Accession Numbers
  • FDB021448
Chemical Information
FooDB Name3-Methyl-2-oxopentanoic acid
Description3-Methyl-2-oxovaleric acid, also known as 3-methyl-2-oxopentanoate or α-keto-β-methyl-N-valeric acid, 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. 3-Methyl-2-oxovaleric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-2-oxovaleric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-Methyl-2-oxovaleric acid has been detected, but not quantified in, several different foods, such as alcoholic beverages, asparagus, cocoa and cocoa products, green vegetables, and milk and milk products. This could make 3-methyl-2-oxovaleric acid a potential biomarker for the consumption of these foods. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. 3-Methyl-2-oxovaleric acid is a potentially toxic compound. A 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. 3-Methyl-2-oxovaleric acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, prosthesis/missing teeth, attachment loss, and missing teeth; 3-methyl-2-oxovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. Used as a clinical marker for maple syrup urine disease (MSUD).
CAS Number1460-34-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-oxo-3-Methyl-N-valeric acidChEBI
2-oxo-3-Methylpentanoic acidChEBI
2-oxo-3-MethylvalerateChEBI
2-oxo-3-Methylvaleric acidChEBI
2-OxoisoleucineChEBI
2-Oxokolavenic acidChEBI
3-Ethyl-3-methylpyruvic acidChEBI
3-Methyl-2-oxopentanoic acidChEBI
alpha-Keto-beta-methyl-N-valeric acidChEBI
alpha-Keto-beta-methylvaleric acidChEBI
alpha-oxo-beta-Methyl-N-valeric acidChEBI
alpha-oxo-beta-Methylvaleric acidChEBI
KetoisoleucineChEBI
2-oxo-3-Methyl-N-valerateGenerator
2-oxo-3-MethylpentanoateGenerator
2-OxokolavenateGenerator
3-Ethyl-3-methylpyruvateGenerator
3-Methyl-2-oxopentanoateGenerator
a-Keto-b-methyl-N-valerateGenerator
a-Keto-b-methyl-N-valeric acidGenerator
alpha-Keto-beta-methyl-N-valerateGenerator
Α-keto-β-methyl-N-valerateGenerator
Α-keto-β-methyl-N-valeric acidGenerator
a-Keto-b-methylvalerateGenerator
a-Keto-b-methylvaleric acidGenerator
alpha-Keto-beta-methylvalerateGenerator
Α-keto-β-methylvalerateGenerator
Α-keto-β-methylvaleric acidGenerator
a-oxo-b-Methyl-N-valerateGenerator
a-oxo-b-Methyl-N-valeric acidGenerator
alpha-oxo-beta-Methyl-N-valerateGenerator
Α-oxo-β-methyl-N-valerateGenerator
Α-oxo-β-methyl-N-valeric acidGenerator
a-oxo-b-MethylvalerateGenerator
a-oxo-b-Methylvaleric acidGenerator
alpha-oxo-beta-MethylvalerateGenerator
Α-oxo-β-methylvalerateGenerator
Α-oxo-β-methylvaleric acidGenerator
3-Methyl-2-oxovalerateGenerator
(3R)-3-Methyl-2-oxopentanoateHMDB
(3R)-3-Methyl-2-oxopentanoic acidHMDB
(R)-3-Methyl-2-oxopentanoateHMDB
(R)-3-Methyl-2-oxopentanoic acidHMDB
(S)-3-Methyl-2-oxopentanoateHMDB
(S)-3-Methyl-2-oxopentanoic acidHMDB
2-Keto-3-methylvalerateHMDB
2-Keto-3-methylvaleric acidHMDB
3-Methyl-2-oxo-pentanoateHMDB
3-Methyl-2-oxo-pentanoic acidHMDB
3-Methyl-2-oxo-valerateHMDB
3-Methyl-2-oxo-valeric acidHMDB
3-Methyl-2-oxovalericHMDB
2-Keto methylvalerateHMDB
KMVAHMDB
alpha-Keto-beta-methylvaleric acid, calcium salt, (S)-isomerHMDB
alpha-Keto-beta-methylvaleric acid, monosodium salt, (S)-isomerHMDB
alpha-Keto-beta-methylvaleric acid, (S)-isomerHMDB
alpha-Keto-beta-methylvaleric acid, calcium saltHMDB
alpha-Keto-beta-methylvaleric acid, sodium salt, (+-)-isomerHMDB
alpha-Keto-beta-methylvaleric acid, (+-)-isomerHMDB
alpha-Keto-beta-methylvaleric acid, sodium saltHMDB
2-keto-3-MethylvalerateHMDB
2-keto-3-Methylvaleric acidHMDB
2-Oxo-3-methyl-n-valeratebiospider
2-Oxo-3-methyl-n-valeric acidbiospider
2-Oxo-3-methylpentanoatebiospider
2-Oxo-3-methylpentanoic acidbiospider
2-Oxo-3-methylvaleratebiospider
2-Oxo-3-methylvaleric acidbiospider
2-oxokolavenatebiospider
2-oxokolavenic acidbiospider
3-methyl-2-oxo-pentanoatebiospider
3-methyl-2-oxo-pentanoic acidbiospider
3-methyl-2-oxo-Valeratebiospider
3-methyl-2-oxo-Valeric acidbiospider
3-Methyl-2-oxovaleric acidChEBI
3-Methyl-2-oxovaleric acid, 8CIdb_source
A-keto-b-methyl-n-valeratebiospider
A-keto-b-methyl-n-valeric acidbiospider
A-keto-b-methylvaleratebiospider
A-keto-b-methylvaleric acidbiospider
A-oxo-b-methyl-n-valeratebiospider
A-oxo-b-methyl-n-valeric acidbiospider
A-oxo-b-methylvaleratebiospider
A-oxo-b-methylvaleric acidbiospider
Alpha-keto-beta-methyl-n-valeratebiospider
Alpha-keto-beta-methyl-n-valeric acidbiospider
Alpha-keto-beta-methylvaleratebiospider
Alpha-keto-beta-methylvaleric acidbiospider
Alpha-oxo-beta-methyl-n-valeratebiospider
Alpha-oxo-beta-methyl-n-valeric acidbiospider
Alpha-oxo-beta-methylvaleratebiospider
Alpha-oxo-beta-methylvaleric acidbiospider
FEMA 3870db_source
α-keto-β-methyl-N-valerateGenerator
α-keto-β-methyl-N-valeric acidGenerator
α-keto-β-methylvalerateGenerator
α-keto-β-methylvaleric acidGenerator
α-oxo-β-methyl-N-valerateGenerator
α-oxo-β-methyl-N-valeric acidGenerator
α-oxo-β-methylvalerateGenerator
α-oxo-β-methylvaleric acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H10O3
IUPAC name3-methyl-2-oxopentanoic acid
InChI IdentifierInChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyJVQYSWDUAOAHFM-UHFFFAOYSA-N
Isomeric SMILESCCC(C)C(=O)C(O)=O
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 55.37%; H 7.74%; O 36.88%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-000i-9610000000-d2ffd4c2796688c555eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-000i-9720000000-9cbc934e100bedd87f17JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-9720000000-5acbdc73aee24c023763JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-6930000000-8c2cf1d8df538010611bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-6930000000-7bef6751c4c607393e5eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0hg9-4950000000-3e1c700a6f553bf63afbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9610000000-d2ffd4c2796688c555eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9720000000-9cbc934e100bedd87f17JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9720000000-5acbdc73aee24c023763JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-6930000000-8c2cf1d8df538010611bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-d08073312b337cdae9e6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05bo-9400000000-9937bff65302162dc3b9JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000w-9300000000-0a6ff60455403c38be39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9000000000-7ee6d2fb63c6ea4cccfaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002b-9000000000-47d18dff23b741029581JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-ae9da2a9acfa56fc6091JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004r-5900000000-a3f740a5c859439255beJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06sr-7900000000-4920c1aefcca814ec1f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-16995fa8eb603d828a2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a6ccc899039a438533aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-5900000000-50107933abbe9c175553JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-9700000000-23998218af9ee2898594JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a30461e2df45eeb8f795JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID46
ChEMBL IDNot Available
KEGG Compound IDC03465
Pubchem Compound ID47
Pubchem Substance IDNot Available
ChEBI ID35932
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00491
CRC / DFC (Dictionary of Food Compounds) IDNVR65-F:NVR65-F
EAFUS ID2435
Dr. Duke IDNot Available
BIGG ID35662
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Branched-chain-amino-acid aminotransferase, cytosolicBCAT1P54687
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT2O15382
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHBP21953
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference