Record Information
Version1.0
Creation date2010-04-08 22:10:16 UTC
Update date2020-09-17 15:38:39 UTC
Primary IDFDB012607
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Methyl-2-oxopentanoic acid
DescriptionKetoleucine, also known as 2-oxoisocaproate or 2-oxoleucine, 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. Ketoleucine is an extremely weak basic (essentially neutral) compound (based on its pKa). Ketoleucine exists in all living species, ranging from bacteria to humans. Outside of the human body, Ketoleucine has been detected, but not quantified in, several different foods, such as oriental wheats, nances, corianders, quinces, and soursops. This could make ketoleucine a potential biomarker for the consumption of these foods. Ketoleucine is a potentially toxic compound. Ketoleucine, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, periodontal probing depth, rheumatoid arthritis, and gout; ketoleucine has also been linked to the inborn metabolic disorder maple syrup urine disease.
CAS Number816-66-0
Structure
Thumb
Synonyms
SynonymSource
2-oxo-4-METHYLPENTANOIC ACIDChEBI
2-OxoisocaproateChEBI
4-Methyl-2-oxopentanoateChEBI
4-Methyl-2-oxovaleric acidChEBI
alpha-Ketoisocaproic acidChEBI
2-oxo-4-METHYLPENTANOateGenerator
2-Oxoisocaproic acidGenerator
4-Methyl-2-oxopentanoic acidGenerator
4-Methyl-2-oxovalerateGenerator
a-KetoisocaproateGenerator
a-Ketoisocaproic acidGenerator
alpha-KetoisocaproateGenerator
Α-ketoisocaproateGenerator
Α-ketoisocaproic acidGenerator
2-Keto-4-methylvalerateHMDB
2-Keto-4-methylvaleric acidHMDB
2-KetoisocaproateHMDB
2-Ketoisocaproic acidHMDB
2-oxo-4-MethylvalerateHMDB
2-oxo-4-Methylvaleric acidHMDB
2-OxoleucineHMDB
4-Methyl-2-oxo-valerateHMDB
4-Methyl-2-oxo-valeric acidHMDB
a-KetoisocapronateHMDB
a-Ketoisocapronic acidHMDB
a-OxoisocaproateHMDB
a-Oxoisocaproic acidHMDB
alpha-Keto-isocaproateHMDB
alpha-Keto-isocaproic acidHMDB
alpha-KetoisocapronateHMDB
alpha-Ketoisocapronic acidHMDB
alpha-OxoisocaproateHMDB
alpha-Oxoisocaproic acidHMDB
KetoisocaproateHMDB
Ketoisocaproic acidHMDB
MethyloxovalerateHMDB
Methyloxovaleric acidHMDB
OxoisocaproateHMDB
Oxoisocaproic acidHMDB
Keto-leucineHMDB
α-ketoisocaproic acidbiospider
2-keto-4-methyl-pentanoatebiospider
2-Keto-4-methylpentanoic acidbiospider
2-keto-4-Methylvaleratebiospider
2-keto-4-Methylvaleric acidbiospider
2-Oxo-4-methylpentanoatebiospider
2-Oxo-4-methylpentanoic acidbiospider
2-Oxo-4-methylvaleratebiospider
2-Oxo-4-methylvaleric acidbiospider
2K-4CH3-PENTANOATEbiospider
4-methyl-2-oxo-Valeratebiospider
4-methyl-2-oxo-Valeric acidbiospider
4-methyl-2-oxovaleric acidbiospider
A-ketoisocaproatebiospider
A-ketoisocaproic acidbiospider
A-ketoisocapronatebiospider
A-ketoisocapronic acidbiospider
A-oxoisocaproatebiospider
A-oxoisocaproic acidbiospider
Alpha-keto-isocaproatebiospider
Alpha-keto-isocaproic acidbiospider
Alpha-ketoisocaproatebiospider
Alpha-ketoisocaproic acidbiospider
Alpha-ketoisocapronatebiospider
Alpha-ketoisocapronic acidbiospider
Alpha-oxoisocaproatebiospider
Alpha-oxoisocaproic acidbiospider
Isobutylglyoxylic aciddb_source
Isopropylpyruvic aciddb_source
Ketoleucinedb_source
KICAdb_source
Pentanoic acid, 4-methyl-2-oxo-biospider
α-ketoisocaproateGenerator
α-ketoisocaproic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility6.76 g/LALOGPS
logP0.82ALOGPS
logP1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.77 m³·mol⁻¹ChemAxon
Polarizability13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10O3
IUPAC name4-methyl-2-oxopentanoic acid
InChI IdentifierInChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyBKAJNAXTPSGJCU-UHFFFAOYSA-N
Isomeric SMILESCC(C)CC(=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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.37%; H 7.74%; O 36.88%DFC
Melting PointMp 10-11° (-1.5°)DFC
Boiling PointBp15 84-85°DFC
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS4-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrumsplash10-000i-9400000000-49d055f04bfe1877ac5bSpectrum
GC-MS4-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrumsplash10-029j-8930000000-c6c54bf6ee2995a2195bSpectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-0ba38257e25873312809Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, 2 TMS, GC-MS Spectrumsplash10-0a5c-4930000000-61247369a805fa2a77a7Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9510000000-8bfc5a54e29f65edf361Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-00lj-9620000000-aa8409ceb2359d903f38Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9400000000-49d055f04bfe1877ac5bSpectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-029j-8930000000-c6c54bf6ee2995a2195bSpectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-0ba38257e25873312809Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-0a5c-4930000000-61247369a805fa2a77a7Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9510000000-8bfc5a54e29f65edf361Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-00lj-9620000000-aa8409ceb2359d903f38Spectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-00ks-7930000000-4e9cfd715fa884d30e7fSpectrum
GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9500000000-709ebcb57f006703c269Spectrum
Predicted GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-e410bce23706f826f8ddSpectrum
Predicted GC-MS4-Methyl-2-oxopentanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9400000000-c4f06cea1e27a2b24660Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-bed7ac074a60210971e3Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9200000000-2fa08d2b4df406cf63eaSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014j-9000000000-045be8e8dca3f93d45baSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-237fa8ad6bfb929be31eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004r-9700000000-8d38d24fce78b1ff13e6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a59-9000000000-759cfc0817917283d1a5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-2a068ada71fbe0a5a988Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9000000000-58e61e31f3c96d84d799Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-237fa8ad6bfb929be31eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-9700000000-8d38d24fce78b1ff13e6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a59-9000000000-759cfc0817917283d1a5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-2a068ada71fbe0a5a988Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-58e61e31f3c96d84d799Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-556a0d1cf568609752d1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004r-5900000000-20f6923c8ed45e9fa088Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08gr-7900000000-31021fda89eb6535185fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btm-9200000000-3bf5df4b557ef87267f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-37839bf70647d24b94a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4900000000-796467909d1d4c087a07Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-9400000000-0abcd021721f32c10e42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015l-9000000000-5c33a47dfeb09a182983Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID69
ChEMBL IDCHEMBL445647
KEGG Compound IDC00233
Pubchem Compound ID70
Pubchem Substance IDNot Available
ChEBI ID48430
Phenol-Explorer IDNot Available
DrugBank IDDB03229
HMDB IDHMDB00695
CRC / DFC (Dictionary of Food Compounds) IDHJH40-C:HJH40-C
EAFUS ID2436
Dr. Duke IDNot Available
BIGG ID34334
KNApSAcK IDC00019677
HET IDCOI
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1047101
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
Flavours
FlavorCitations
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference