Livestock Metabolome Database: Showing metabocard for 3-Methyl-2-oxovaleric acid (LMDB01097)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2020-03-06 18:22:55 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB01097

Secondary Accession Numbers

None

Metabolite 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).

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

Not Available

Average Molecular Weight

Not Available

Monoisotopic Molecular Weight

Not Available

IUPAC Name

3-methyl-2-oxopentanoic acid

Traditional Name

3-methyl-2-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

InChI Identifier

Not Available

InChI Key

Not Available

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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000i-9610000000-d2ffd4c2796688c555ee	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000i-9720000000-9cbc934e100bedd87f17	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-9720000000-5acbdc73aee24c023763	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-6930000000-8c2cf1d8df538010611b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-6930000000-7bef6751c4c607393e5e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0hg9-4950000000-3e1c700a6f553bf63afb	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9610000000-d2ffd4c2796688c555ee	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9720000000-9cbc934e100bedd87f17	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9720000000-5acbdc73aee24c023763	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-6930000000-8c2cf1d8df538010611b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9000000000-d08073312b337cdae9e6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05bo-9400000000-9937bff65302162dc3b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000w-9300000000-0a6ff60455403c38be39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9000000000-7ee6d2fb63c6ea4cccfa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002b-9000000000-47d18dff23b741029581	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-ae9da2a9acfa56fc6091	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004r-5900000000-a3f740a5c859439255be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06sr-7900000000-4920c1aefcca814ec1f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-16995fa8eb603d828a2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a6ccc899039a438533ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-50107933abbe9c175553	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ri-9700000000-23998218af9ee2898594	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a30461e2df45eeb8f795	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected and Quantified	1.9102 +/- 0.0578 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.2681 +/- 1.1307 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.2336 +/- 0.5427 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.25 +/- 0.85 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	2.4681 +/- 1.8349 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9073 +/- 0.037 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9 +/- 0.0 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.0136 +/- 0.3856 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9784 +/- 0.2416 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.0013 +/- 0.3334 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9515 +/- 0.1363 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.0296 +/- 0.3021 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.4941 +/- 1.1191 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.1145 +/- 0.6617 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9 +/- 0.0 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.0493 +/- 0.3099 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9047 +/- 0.0172 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.4398 +/- 0.9801 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.4689 +/- 1.4996 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.5545 +/- 1.1209 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9464 +/- 0.1413 uM	Normal	Ovine	Goldansaz et al.,...	details