Record Information
Version1.0
Created at2020-04-17 18:43:57 UTC
Updated at2020-12-07 19:11:07 UTC
CannabisDB IDCDB004857
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameKetoleucine
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. Ketoleucine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC6H10O3
Average Molecular Weight130.14
Monoisotopic Molecular Weight130.063
IUPAC Name4-methyl-2-oxopentanoic acid
Traditional Nameketoisocaproate
CAS Registry Number816-66-0
SMILES
CC(C)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyBKAJNAXTPSGJCU-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:

Biological role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point8 - 10 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility32 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSKetoleucine, 3 TMS, GC-MS Spectrumsplash10-000i-9400000000-49d055f04bfe1877ac5bSpectrum
GC-MSKetoleucine, 3 TMS, GC-MS Spectrumsplash10-029j-8930000000-c6c54bf6ee2995a2195bSpectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-0ba38257e25873312809Spectrum
GC-MSKetoleucine, 2 TMS, GC-MS Spectrumsplash10-0a5c-4930000000-61247369a805fa2a77a7Spectrum
GC-MSKetoleucine, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9510000000-8bfc5a54e29f65edf361Spectrum
GC-MSKetoleucine, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-00lj-9620000000-aa8409ceb2359d903f38Spectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-000i-9400000000-49d055f04bfe1877ac5bSpectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-029j-8930000000-c6c54bf6ee2995a2195bSpectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-0ba38257e25873312809Spectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-0a5c-4930000000-61247369a805fa2a77a7Spectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-000i-9510000000-8bfc5a54e29f65edf361Spectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-00lj-9620000000-aa8409ceb2359d903f38Spectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-00ks-7930000000-4e9cfd715fa884d30e7fSpectrum
GC-MSKetoleucine, non-derivatized, GC-MS Spectrumsplash10-000i-9500000000-709ebcb57f006703c269Spectrum
Predicted GC-MSKetoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-e410bce23706f826f8ddSpectrum
Predicted GC-MSKetoleucine, 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
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
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 IDHMDB0000695
DrugBank IDDB03229
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030510
KNApSAcK IDC00019677
Chemspider ID69
KEGG Compound IDC00233
BioCyc ID2K-4CH3-PENTANOATE
BiGG ID34334
Wikipedia LinkNot Available
METLIN ID5663
PubChem Compound70
PDB IDNot Available
ChEBI ID48430
References
General ReferencesNot Available

Enzymes

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
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
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
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