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4-Methyl-2-oxopentanoic acid (FDB012607)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
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
Predicted GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-2-oxopentanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-2-oxopentanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-2-oxopentanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-bed7ac074a60210971e32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9200000000-2fa08d2b4df406cf63ea2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014j-9000000000-045be8e8dca3f93d45ba2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-237fa8ad6bfb929be31e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004r-9700000000-8d38d24fce78b1ff13e62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a59-9000000000-759cfc0817917283d1a52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-2a068ada71fbe0a5a9882012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9000000000-58e61e31f3c96d84d7992012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-237fa8ad6bfb929be31e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-9700000000-8d38d24fce78b1ff13e62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a59-9000000000-759cfc0817917283d1a52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-2a068ada71fbe0a5a9882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-58e61e31f3c96d84d7992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-556a0d1cf568609752d12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004r-5900000000-20f6923c8ed45e9fa0882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0900000000-b66d521478c92e2d77d02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-9c3a698d9f28af574ef62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-47ced70de4860e9002832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03xr-7900000000-0461a5a56e36a03fe5222021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08gr-7900000000-31021fda89eb6535185f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btm-9200000000-3bf5df4b557ef87267f42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-37839bf70647d24b94a42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4900000000-796467909d1d4c087a072015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-9400000000-0abcd021721f32c10e422015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015l-9000000000-5c33a47dfeb09a1829832015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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