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3-Methyl-2-oxobutanoic acid (FDB012250)

Record Information
Version1.0
Creation date2010-04-08 22:10:04 UTC
Update date2020-09-17 15:38:09 UTC
Primary IDFDB012250
Secondary Accession Numbers
  • FDB030441
Chemical Information
FooDB Name3-Methyl-2-oxobutanoic acid
Descriptionalpha-Ketoisovaleric acid, also known as a-keto-isovalerate or 3-methyl-2-oxobutanoate, 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. alpha-Ketoisovaleric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. alpha-Ketoisovaleric acid exists in all living species, ranging from bacteria to humans. alpha-Ketoisovaleric acid is a fruity tasting compound. Outside of the human body, alpha-Ketoisovaleric acid has been detected, but not quantified in, several different foods, such as root vegetables, jerusalem artichokes, rapinis, chia, and cowpea. This could make alpha-ketoisovaleric acid a potential biomarker for the consumption of these foods. alpha-Ketoisovaleric acid is a potentially toxic compound. alpha-Ketoisovaleric acid, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; alpha-ketoisovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.
CAS Number759-05-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility30.2 g/LALOGPS
logP0.49ALOGPS
logP1.31ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity27.19 m³·mol⁻¹ChemAxon
Polarizability11.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O3
IUPAC name3-methyl-2-oxobutanoic acid
InChI IdentifierInChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)
InChI KeyQHKABHOOEWYVLI-UHFFFAOYSA-N
Isomeric SMILESCC(C)C(=O)C(O)=O
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 51.72%; H 6.94%; O 41.34%DFC
Melting PointMp 31°DFC
Boiling PointBp 170.5°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-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9500000000-ff936b879a69b5d118f8Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-8920000000-e37b37d64d43dcf763f0Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9400000000-e3995acc4818a98d0f48Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-0f79-9720000000-5d89487273e44ea61a68Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9700000000-209c737dcac7df2b198cSpectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0f79-5920000000-759a2f01b4f52767ade2Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9500000000-ff936b879a69b5d118f8Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-8920000000-e37b37d64d43dcf763f0Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9400000000-e3995acc4818a98d0f48Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0f79-9720000000-5d89487273e44ea61a68Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-7900000000-7e325567183fb56996d5Spectrum
GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0ufr-0930000000-be90b06add7135b4a539Spectrum
Predicted GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9000000000-52f9d8fc8386e4c512feSpectrum
Predicted GC-MS3-Methyl-2-oxobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9600000000-52aefdc997dac92c8459Spectrum
Predicted GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methyl-2-oxobutanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methyl-2-oxobutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methyl-2-oxobutanoic 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)splash10-000i-9000000000-10ab58a33e9ca7dbace02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-ad51ff01c94b6046ad642012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-9993174a7b1801b90ddb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00xr-9500000000-293818b81e0879b6feb22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-75058f27a2178b9cf1212012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-4c20af39e8ee009d52782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-9993174a7b1801b90ddb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00xr-9500000000-1a58c6a6b4f5477dabdd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-75058f27a2178b9cf1212017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-cc4465a47e663be66df52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00di-9100000000-19511890852fce513a022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9300000000-30d3bdfb6d38dbb8e1012021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000l-9000000000-879b6502ff380673b7762021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0159-9800000000-0cf4d3a0e7b3356995c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014o-9900000000-f35430a2eaea0d81df322021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r2-9400000000-21f8c3fae79161c820992015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-5f25e41413738bb6b5d72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-801af00dea93fcfd637d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-8900000000-5185c7dfc72c250699042015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9200000000-7e2a275a65197f96f5d72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0600-9000000000-0013e0ff06f9896a13372015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-6900000000-7f00871b074cbd9a42e62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06di-9400000000-6d56778068e11e4f8e852021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-b445e7fc67a8ff2bd3ba2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-9000000000-733fb7227d2d053b112f2021-09-25View 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, 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
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, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
ChemSpider ID48
ChEMBL IDCHEMBL146554
KEGG Compound IDC00141
Pubchem Compound ID49
Pubchem Substance IDNot Available
ChEBI ID16530
Phenol-Explorer IDNot Available
DrugBank IDDB04074
HMDB IDHMDB00019
CRC / DFC (Dictionary of Food Compounds) IDHFL26-U:HFL26-U
EAFUS ID2433
Dr. Duke IDNot Available
BIGG ID34011
KNApSAcK IDC00007623
HET IDKIV
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1047091
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
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHBP11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrialPDHA2P29803
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHBP21953
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialDLATP10515
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