Cannabis Compound Database: Showing Compound Card for Ketoleucine (CDB004857)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4) Show 5 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:43:57 UTC

Updated at

2020-12-07 19:11:07 UTC

CannabisDB ID

CDB004857

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Ketoleucine

Description

Ketoleucine, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-oxo-4-METHYLPENTANOIC ACID	ChEBI
2-Oxoisocaproate	ChEBI
4-Methyl-2-oxopentanoate	ChEBI
4-Methyl-2-oxovaleric acid	ChEBI
alpha-Ketoisocaproic acid	ChEBI
2-oxo-4-METHYLPENTANOate	Generator
2-Oxoisocaproic acid	Generator
4-Methyl-2-oxopentanoic acid	Generator
4-Methyl-2-oxovalerate	Generator
a-Ketoisocaproate	Generator
a-Ketoisocaproic acid	Generator
alpha-Ketoisocaproate	Generator
Α-ketoisocaproate	Generator
Α-ketoisocaproic acid	Generator
2-Keto-4-methylvalerate	HMDB
2-Keto-4-methylvaleric acid	HMDB
2-Ketoisocaproate	HMDB
2-Ketoisocaproic acid	HMDB
2-oxo-4-Methylvalerate	HMDB
2-oxo-4-Methylvaleric acid	HMDB
2-Oxoleucine	HMDB
4-Methyl-2-oxo-valerate	HMDB
4-Methyl-2-oxo-valeric acid	HMDB
a-Ketoisocapronate	HMDB
a-Ketoisocapronic acid	HMDB
a-Oxoisocaproate	HMDB
a-Oxoisocaproic acid	HMDB
alpha-Keto-isocaproate	HMDB
alpha-Keto-isocaproic acid	HMDB
alpha-Ketoisocapronate	HMDB
alpha-Ketoisocapronic acid	HMDB
alpha-Oxoisocaproate	HMDB
alpha-Oxoisocaproic acid	HMDB
Ketoisocaproate	HMDB
Ketoisocaproic acid	HMDB
Methyloxovalerate	HMDB
Methyloxovaleric acid	HMDB
Oxoisocaproate	HMDB
Oxoisocaproic acid	HMDB
Keto-leucine	HMDB

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.14

Monoisotopic Molecular Weight

130.063

IUPAC Name

4-methyl-2-oxopentanoic acid

Traditional Name

ketoisocaproate

CAS Registry Number

816-66-0

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 Key

BKAJNAXTPSGJCU-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-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 Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:48430 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	8 - 10 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	32 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.82	ALOGPS
logP	1.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.77 m³·mol⁻¹	ChemAxon
Polarizability	13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Ketoleucine, 3 TMS, GC-MS Spectrum	splash10-000i-9400000000-49d055f04bfe1877ac5b	Spectrum
GC-MS	Ketoleucine, 3 TMS, GC-MS Spectrum	splash10-029j-8930000000-c6c54bf6ee2995a2195b	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-0ba38257e25873312809	Spectrum
GC-MS	Ketoleucine, 2 TMS, GC-MS Spectrum	splash10-0a5c-4930000000-61247369a805fa2a77a7	Spectrum
GC-MS	Ketoleucine, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-9510000000-8bfc5a54e29f65edf361	Spectrum
GC-MS	Ketoleucine, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-00lj-9620000000-aa8409ceb2359d903f38	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-000i-9400000000-49d055f04bfe1877ac5b	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-029j-8930000000-c6c54bf6ee2995a2195b	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-0ba38257e25873312809	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-0a5c-4930000000-61247369a805fa2a77a7	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-000i-9510000000-8bfc5a54e29f65edf361	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-00lj-9620000000-aa8409ceb2359d903f38	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-00ks-7930000000-4e9cfd715fa884d30e7f	Spectrum
GC-MS	Ketoleucine, non-derivatized, GC-MS Spectrum	splash10-000i-9500000000-709ebcb57f006703c269	Spectrum
Predicted GC-MS	Ketoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-e410bce23706f826f8dd	Spectrum
Predicted GC-MS	Ketoleucine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9400000000-c4f06cea1e27a2b24660	Spectrum
Predicted GC-MS	Ketoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ketoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ketoleucine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ketoleucine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ketoleucine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9000000000-bed7ac074a60210971e3	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9200000000-2fa08d2b4df406cf63ea	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014j-9000000000-045be8e8dca3f93d45ba	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-237fa8ad6bfb929be31e	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004r-9700000000-8d38d24fce78b1ff13e6	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a59-9000000000-759cfc0817917283d1a5	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4l-9000000000-2a068ada71fbe0a5a988	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4l-9000000000-58e61e31f3c96d84d799	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-237fa8ad6bfb929be31e	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004r-9700000000-8d38d24fce78b1ff13e6	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a59-9000000000-759cfc0817917283d1a5	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-2a068ada71fbe0a5a988	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-58e61e31f3c96d84d799	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-556a0d1cf568609752d1	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004r-5900000000-20f6923c8ed45e9fa088	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-b66d521478c92e2d77d0	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-9c3a698d9f28af574ef6	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-47ced70de4860e900283	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-7900000000-0461a5a56e36a03fe522	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08gr-7900000000-31021fda89eb6535185f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0btm-9200000000-3bf5df4b557ef87267f4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-37839bf70647d24b94a4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-4900000000-796467909d1d4c087a07	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ri-9400000000-0abcd021721f32c10e42	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015l-9000000000-5c33a47dfeb09a182983	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Valine, Leucine and Isoleucine Degradation
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	BCKDHB	6q14.1	P21953	details
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial	BCKDHA	19q13.1-q13.2	P12694	details
Branched-chain-amino-acid aminotransferase, cytosolic	BCAT1	12p12.1	P54687	details
Branched-chain-amino-acid aminotransferase, mitochondrial	BCAT2	19q13	O15382	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial	BCKDHA	19q13.1-q13.2	P12694	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000695

DrugBank ID

DB03229

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030510

KNApSAcK ID

C00019677

Chemspider ID

KEGG Compound ID

C00233

BioCyc ID

2K-4CH3-PENTANOATE

BiGG ID

34334

Wikipedia Link

Not Available

METLIN ID

5663

PubChem Compound

PDB ID

Not Available

ChEBI ID

48430

References

General References

Not 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

Showing Compound Card for Ketoleucine (CDB004857)

Structure for CDB004857 (Ketoleucine)

Enzymes