Showing Compound Card for 3-Methyl-2-oxovaleric acid (CDB005123)

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Record Information
Version1.0
Created at2020-04-17 19:11:37 UTC
Updated at2020-12-07 19:11:38 UTC
CannabisDB IDCDB005123
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Methyl-2-oxovaleric 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). 3-Methyl-2-oxovaleric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC6H10O3
Average Molecular Weight130.14
Monoisotopic Molecular Weight130.063
IUPAC Name3-methyl-2-oxopentanoic acid
Traditional Name3-methyl-2-oxopentanoic acid
CAS Registry Number1460-34-0
SMILES
CCC(C)C(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyJVQYSWDUAOAHFM-UHFFFAOYSA-N
Chemical Taxonomy
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:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility915.5 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Methyl-2-oxovaleric acid, 3 TMS, GC-MS Spectrumsplash10-000i-9610000000-d2ffd4c2796688c555eeSpectrum
GC-MS3-Methyl-2-oxovaleric acid, 3 TMS, GC-MS Spectrumsplash10-000i-9720000000-9cbc934e100bedd87f17Spectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-000i-9720000000-5acbdc73aee24c023763Spectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-000i-6930000000-8c2cf1d8df538010611bSpectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-000i-6930000000-7bef6751c4c607393e5eSpectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-0hg9-4950000000-3e1c700a6f553bf63afbSpectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-000i-9610000000-d2ffd4c2796688c555eeSpectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-000i-9720000000-9cbc934e100bedd87f17Spectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-000i-9720000000-5acbdc73aee24c023763Spectrum
GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrumsplash10-000i-6930000000-8c2cf1d8df538010611bSpectrum
Predicted GC-MS3-Methyl-2-oxovaleric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-9000000000-d08073312b337cdae9e6Spectrum
Predicted GC-MS3-Methyl-2-oxovaleric 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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHB6q14.1P21953 details
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrialBCKDHA19q13.1-q13.2P12694 details
Branched-chain-amino-acid aminotransferase, cytosolicBCAT112p12.1P54687 details
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT219q13O15382 details
L-amino-acid oxidaseIL4I119q13.3-q13.4Q96RQ9 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrialBCKDHA19q13.1-q13.2P12694 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000491
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021447
KNApSAcK IDNot Available
Chemspider ID46
KEGG Compound IDC03465
BioCyc IDNot Available
BiGG ID35662
Wikipedia LinkNot Available
METLIN ID5478
PubChem Compound47
PDB IDNot Available
ChEBI ID35932
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
General function:
Involved in catalytic activity
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21953
Molecular weight:
43122.065
Enzyme Details
2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P12694
Molecular weight:
50470.58
Enzyme Details
3. Branched-chain-amino-acid aminotransferase, cytosolic
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:
BCAT1
Uniprot ID:
P54687
Molecular weight:
38644.77
Enzyme Details
4. Branched-chain-amino-acid aminotransferase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
Gene Name:
BCAT2
Uniprot ID:
O15382
Molecular weight:
33776.315
Enzyme Details
5. L-amino-acid oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:
IL4I1
Uniprot ID:
Q96RQ9
Molecular weight:
65327.26