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

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:11:37 UTC

Updated at

2020-12-07 19:11:38 UTC

CannabisDB ID

CDB005123

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

3-Methyl-2-oxovaleric acid

Description

3-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-oxo-3-Methyl-N-valeric acid	ChEBI
2-oxo-3-Methylpentanoic acid	ChEBI
2-oxo-3-Methylvalerate	ChEBI
2-oxo-3-Methylvaleric acid	ChEBI
2-Oxoisoleucine	ChEBI
2-Oxokolavenic acid	ChEBI
3-Ethyl-3-methylpyruvic acid	ChEBI
3-Methyl-2-oxopentanoic acid	ChEBI
alpha-Keto-beta-methyl-N-valeric acid	ChEBI
alpha-Keto-beta-methylvaleric acid	ChEBI
alpha-oxo-beta-Methyl-N-valeric acid	ChEBI
alpha-oxo-beta-Methylvaleric acid	ChEBI
Ketoisoleucine	ChEBI
2-oxo-3-Methyl-N-valerate	Generator
2-oxo-3-Methylpentanoate	Generator
2-Oxokolavenate	Generator
3-Ethyl-3-methylpyruvate	Generator
3-Methyl-2-oxopentanoate	Generator
a-Keto-b-methyl-N-valerate	Generator
a-Keto-b-methyl-N-valeric acid	Generator
alpha-Keto-beta-methyl-N-valerate	Generator
Α-keto-β-methyl-N-valerate	Generator
Α-keto-β-methyl-N-valeric acid	Generator
a-Keto-b-methylvalerate	Generator
a-Keto-b-methylvaleric acid	Generator
alpha-Keto-beta-methylvalerate	Generator
Α-keto-β-methylvalerate	Generator
Α-keto-β-methylvaleric acid	Generator
a-oxo-b-Methyl-N-valerate	Generator
a-oxo-b-Methyl-N-valeric acid	Generator
alpha-oxo-beta-Methyl-N-valerate	Generator
Α-oxo-β-methyl-N-valerate	Generator
Α-oxo-β-methyl-N-valeric acid	Generator
a-oxo-b-Methylvalerate	Generator
a-oxo-b-Methylvaleric acid	Generator
alpha-oxo-beta-Methylvalerate	Generator
Α-oxo-β-methylvalerate	Generator
Α-oxo-β-methylvaleric acid	Generator
3-Methyl-2-oxovalerate	Generator
(3R)-3-Methyl-2-oxopentanoate	HMDB
(3R)-3-Methyl-2-oxopentanoic acid	HMDB
(R)-3-Methyl-2-oxopentanoate	HMDB
(R)-3-Methyl-2-oxopentanoic acid	HMDB
(S)-3-Methyl-2-oxopentanoate	HMDB
(S)-3-Methyl-2-oxopentanoic acid	HMDB
2-Keto-3-methylvalerate	HMDB
2-Keto-3-methylvaleric acid	HMDB
3-Methyl-2-oxo-pentanoate	HMDB
3-Methyl-2-oxo-pentanoic acid	HMDB
3-Methyl-2-oxo-valerate	HMDB
3-Methyl-2-oxo-valeric acid	HMDB
3-Methyl-2-oxovaleric	HMDB
2-Keto methylvalerate	HMDB
KMVA	HMDB
alpha-Keto-beta-methylvaleric acid, calcium salt, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, monosodium salt, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, calcium salt	HMDB
alpha-Keto-beta-methylvaleric acid, sodium salt, (+-)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, (+-)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, sodium salt	HMDB

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.14

Monoisotopic Molecular Weight

130.063

IUPAC Name

3-methyl-2-oxopentanoic acid

Traditional Name

3-methyl-2-oxopentanoic acid

CAS Registry Number

1460-34-0

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 Key

JVQYSWDUAOAHFM-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:35932 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Theobroma cacao

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	915.5 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1	ALOGPS
logP	1.75	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.52	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	31.79 m³·mol⁻¹	ChemAxon
Polarizability	13.09 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	3-Methyl-2-oxovaleric acid, 3 TMS, GC-MS Spectrum	splash10-000i-9610000000-d2ffd4c2796688c555ee	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, 3 TMS, GC-MS Spectrum	splash10-000i-9720000000-9cbc934e100bedd87f17	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-000i-9720000000-5acbdc73aee24c023763	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-000i-6930000000-8c2cf1d8df538010611b	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-000i-6930000000-7bef6751c4c607393e5e	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-0hg9-4950000000-3e1c700a6f553bf63afb	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-000i-9610000000-d2ffd4c2796688c555ee	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-000i-9720000000-9cbc934e100bedd87f17	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-000i-9720000000-5acbdc73aee24c023763	Spectrum
GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, GC-MS Spectrum	splash10-000i-6930000000-8c2cf1d8df538010611b	Spectrum
Predicted GC-MS	3-Methyl-2-oxovaleric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-056r-9000000000-d08073312b337cdae9e6	Spectrum
Predicted GC-MS	3-Methyl-2-oxovaleric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05bo-9400000000-9937bff65302162dc3b9	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000w-9300000000-0a6ff60455403c38be39	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9000000000-7ee6d2fb63c6ea4cccfa	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002b-9000000000-47d18dff23b741029581	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-ae9da2a9acfa56fc6091	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004r-5900000000-a3f740a5c859439255be	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06sr-7900000000-4920c1aefcca814ec1f6	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-16995fa8eb603d828a2f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a6ccc899039a438533ae	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-50107933abbe9c175553	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ri-9700000000-23998218af9ee2898594	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a30461e2df45eeb8f795	Spectrum

NMR

Type	Description	View
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
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
L-amino-acid oxidase	IL4I1	19q13.3-q13.4	Q96RQ9	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

HMDB0000491

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021447

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

C03465

BioCyc ID

Not Available

BiGG ID

35662

Wikipedia Link

Not Available

METLIN ID

5478

PubChem Compound

PDB ID

Not Available

ChEBI ID

35932

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

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

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

Structure for CDB005123 (3-Methyl-2-oxovaleric acid)

Enzymes