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

Record Information
Version1.0
Creation date2010-04-08 22:15:42 UTC
Update date2024-11-29 22:27:40 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
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrumsplash10-000i-9610000000-d2ffd4c2796688c555eeSpectrum
GC-MS3-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrumsplash10-000i-9720000000-9cbc934e100bedd87f17Spectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9720000000-5acbdc73aee24c023763Spectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-6930000000-8c2cf1d8df538010611bSpectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-6930000000-7bef6751c4c607393e5eSpectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-0hg9-4950000000-3e1c700a6f553bf63afbSpectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9610000000-d2ffd4c2796688c555eeSpectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9720000000-9cbc934e100bedd87f17Spectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9720000000-5acbdc73aee24c023763Spectrum
GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-6930000000-8c2cf1d8df538010611bSpectrum
Predicted GC-MS3-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-9000000000-d08073312b337cdae9e6Spectrum
Predicted GC-MS3-Methyl-2-oxopentanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05bo-9400000000-9937bff65302162dc3b9Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000w-9300000000-0a6ff60455403c38be392012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9000000000-7ee6d2fb63c6ea4cccfa2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002b-9000000000-47d18dff23b7410295812012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-ae9da2a9acfa56fc60912017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004r-5900000000-a3f740a5c859439255be2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06sr-7900000000-4920c1aefcca814ec1f62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-16995fa8eb603d828a2f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a6ccc899039a438533ae2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-5900000000-50107933abbe9c1755532017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-9700000000-23998218af9ee28985942017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a30461e2df45eeb8f7952017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference