Showing Compound 3-Methyl-2-oxopentanoic acid (FDB021447)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:42 UTC

Update date

2024-11-29 22:27:40 UTC

Primary ID

FDB021447

Secondary Accession Numbers

FDB021448

Chemical Information

FooDB Name

3-Methyl-2-oxopentanoic 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).

CAS Number

1460-34-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
2-keto-3-Methylvalerate	HMDB
2-keto-3-Methylvaleric acid	HMDB
2-Oxo-3-methyl-n-valerate	biospider
2-Oxo-3-methyl-n-valeric acid	biospider
2-Oxo-3-methylpentanoate	biospider
2-Oxo-3-methylpentanoic acid	biospider
2-Oxo-3-methylvalerate	biospider
2-Oxo-3-methylvaleric acid	biospider
2-oxokolavenate	biospider
2-oxokolavenic acid	biospider
3-methyl-2-oxo-pentanoate	biospider
3-methyl-2-oxo-pentanoic acid	biospider
3-methyl-2-oxo-Valerate	biospider
3-methyl-2-oxo-Valeric acid	biospider
3-Methyl-2-oxovaleric acid	ChEBI
3-Methyl-2-oxovaleric acid, 8CI	db_source
A-keto-b-methyl-n-valerate	biospider
A-keto-b-methyl-n-valeric acid	biospider
A-keto-b-methylvalerate	biospider
A-keto-b-methylvaleric acid	biospider
A-oxo-b-methyl-n-valerate	biospider
A-oxo-b-methyl-n-valeric acid	biospider
A-oxo-b-methylvalerate	biospider
A-oxo-b-methylvaleric acid	biospider
Alpha-keto-beta-methyl-n-valerate	biospider
Alpha-keto-beta-methyl-n-valeric acid	biospider
Alpha-keto-beta-methylvalerate	biospider
Alpha-keto-beta-methylvaleric acid	biospider
Alpha-oxo-beta-methyl-n-valerate	biospider
Alpha-oxo-beta-methyl-n-valeric acid	biospider
Alpha-oxo-beta-methylvalerate	biospider
Alpha-oxo-beta-methylvaleric acid	biospider
FEMA 3870	db_source
α-keto-β-methyl-N-valerate	Generator
α-keto-β-methyl-N-valeric acid	Generator
α-keto-β-methylvalerate	Generator
α-keto-β-methylvaleric acid	Generator
α-oxo-β-methyl-N-valerate	Generator
α-oxo-β-methyl-N-valeric acid	Generator
α-oxo-β-methylvalerate	Generator
α-oxo-β-methylvaleric acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	9.86 g/L	ALOGPS
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

Chemical Formula

C6H10O3

IUPAC name

3-methyl-2-oxopentanoic acid

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

Isomeric SMILES

CCC(C)C(=O)C(O)=O

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

Classification

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:

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Indirect biological role:

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 55.37%; H 7.74%; O 36.88%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	3-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrum	splash10-000i-9610000000-d2ffd4c2796688c555ee	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrum	splash10-000i-9720000000-9cbc934e100bedd87f17	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9720000000-5acbdc73aee24c023763	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-6930000000-8c2cf1d8df538010611b	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-6930000000-7bef6751c4c607393e5e	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-0hg9-4950000000-3e1c700a6f553bf63afb	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9610000000-d2ffd4c2796688c555ee	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9720000000-9cbc934e100bedd87f17	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9720000000-5acbdc73aee24c023763	Spectrum
GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-6930000000-8c2cf1d8df538010611b	Spectrum
Predicted GC-MS	3-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-056r-9000000000-d08073312b337cdae9e6	Spectrum
Predicted GC-MS	3-Methyl-2-oxopentanoic 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	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9000000000-7ee6d2fb63c6ea4cccfa	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002b-9000000000-47d18dff23b741029581	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-ae9da2a9acfa56fc6091	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004r-5900000000-a3f740a5c859439255be	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06sr-7900000000-4920c1aefcca814ec1f6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-16995fa8eb603d828a2f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a6ccc899039a438533ae	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-50107933abbe9c175553	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ri-9700000000-23998218af9ee2898594	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a30461e2df45eeb8f795	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

Not Available

KEGG Compound ID

C03465

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

35932

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00491

CRC / DFC (Dictionary of Food Compounds) ID

NVR65-F:NVR65-F

EAFUS ID

2435

Dr. Duke ID

Not Available

BIGG ID

35662

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Branched-chain-amino-acid aminotransferase, cytosolic	BCAT1	P54687
Branched-chain-amino-acid aminotransferase, mitochondrial	BCAT2	O15382
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	BCKDHB	P21953