Showing Compound 3-Methyl-2-oxobutanoic acid (FDB012250)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:04 UTC

Update date

2020-09-17 15:38:09 UTC

Primary ID

FDB012250

Secondary Accession Numbers

FDB030441

Chemical Information

FooDB Name

3-Methyl-2-oxobutanoic acid

Description

alpha-Ketoisovaleric acid, also known as a-keto-isovalerate or 3-methyl-2-oxobutanoate, 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. alpha-Ketoisovaleric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. alpha-Ketoisovaleric acid exists in all living species, ranging from bacteria to humans. alpha-Ketoisovaleric acid is a fruity tasting compound. Outside of the human body, alpha-Ketoisovaleric acid has been detected, but not quantified in, several different foods, such as root vegetables, jerusalem artichokes, rapinis, chia, and cowpea. This could make alpha-ketoisovaleric acid a potential biomarker for the consumption of these foods. alpha-Ketoisovaleric acid is a potentially toxic compound. alpha-Ketoisovaleric acid, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; alpha-ketoisovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.

CAS Number

759-05-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Keto-3-methylbutyric acid	ChEBI
2-Ketoisovaleric acid	ChEBI
2-Ketovaline	ChEBI
2-oxo-3-Methylbutanoic acid	ChEBI
2-oxo-3-Methylbutyric acid	ChEBI
2-Oxoisovaleric acid	ChEBI
3-Methyl-2-oxobutanoate	ChEBI
3-Methyl-2-oxobutyric acid	ChEBI
alpha-Keto-isovaleric acid	ChEBI
alpha-Ketovaline	ChEBI
alpha-oxo-beta-Methylbutyricacid	ChEBI
alpha-Oxoisovaleric acid	ChEBI
Dimethylpyruvic acid	ChEBI
Isopropylglyoxylic acid	ChEBI
2-oxo-3-Methylbutanoate	Kegg
2-Oxoisovalerate	Kegg
2-Oxoisopentanoate	Kegg
2-Keto-3-methylbutyrate	Generator
2-Ketoisovalerate	Generator
2-oxo-3-Methylbutyrate	Generator
3-Methyl-2-oxobutanoic acid	Generator
3-Methyl-2-oxobutyrate	Generator
a-Keto-isovalerate	Generator
a-Keto-isovaleric acid	Generator
alpha-Keto-isovalerate	Generator
Α-keto-isovalerate	Generator
Α-keto-isovaleric acid	Generator
a-Ketovaline	Generator
Α-ketovaline	Generator
a-oxo-b-Methylbutyricacid	Generator
Α-oxo-β-methylbutyricacid	Generator
a-Oxoisovalerate	Generator
a-Oxoisovaleric acid	Generator
alpha-Oxoisovalerate	Generator
Α-oxoisovalerate	Generator
Α-oxoisovaleric acid	Generator
Dimethylpyruvate	Generator
Isopropylglyoxylate	Generator
2-Oxoisopentanoic acid	Generator
a-Ketoisovalerate	Generator
a-Ketoisovaleric acid	Generator
alpha-Ketoisovalerate	Generator
Α-ketoisovalerate	Generator
Α-ketoisovaleric acid	Generator
2-Ketoisvaleric acid	HMDB
2-oxo-3-Methyl-butyrate	HMDB
3-Methyl-2-oxo-butanoate	HMDB
3-Methyl-2-oxo-butanoic acid	HMDB
3-Methyl-2-oxo-butyrate	HMDB
3-Methyl-2-oxo-butyric acid	HMDB
3-Methyl-2-oxobutinoate	HMDB
3-Methyl-2-oxobutinoic acid	HMDB
a-Keto-b-methylbutyrate	HMDB
a-Keto-b-methylbutyric acid	HMDB
a-oxo-b-Methylbutyrate	HMDB
a-oxo-b-Methylbutyric acid	HMDB
alpha-Keto-beta-methylbutyrate	HMDB
alpha-Keto-beta-methylbutyric acid	HMDB
alpha-oxo-beta-Methylbutyrate	HMDB
alpha-oxo-beta-Methylbutyric acid	HMDB
Ketovaline	HMDB
alpha-Ketoisopentanoic acid	HMDB
alpha-Ketoisovaleric acid	Generator, MeSH
2-keto-3-Methylbutyrate	biospider
2-keto-3-Methylbutyric acid	ChEBI
2-KETO-ISOVALERATE	biospider
2-Oxo-3-methylbutanoic acid	biospider
2-Oxo-3-methylbutyrate	biospider
2-Oxo-3-methylbutyric acid	biospider
3-methyl-2-oxo-Butanoate	biospider
3-methyl-2-oxo-Butanoic acid	biospider
3-methyl-2-oxo-Butyrate	biospider
3-methyl-2-oxo-Butyric acid	biospider
A-keto-b-methylbutyrate	biospider
A-keto-b-methylbutyric acid	biospider
A-keto-isovalerate	biospider
A-keto-isovaleric acid	biospider
A-ketoisovalerate	biospider
A-oxo-b-methylbutyrate	biospider
A-oxo-b-methylbutyric acid	biospider
A-oxoisovalerate	biospider
A-oxoisovaleric acid	biospider
Alpha-keto-beta-methylbutyrate	biospider
Alpha-keto-beta-methylbutyric acid	biospider
Alpha-keto-isovalerate	biospider
Alpha-keto-isovaleric acid	biospider
Alpha-keto-valine	biospider
Alpha-ketoisopentanoic acid	biospider
Alpha-ketoisovalerate	biospider
Alpha-ketoisovaleric acid	biospider
Alpha-oxo-beta-methylbutyrate	biospider
Alpha-oxo-beta-methylbutyric acid	biospider
Alpha-oxoisovalerate	biospider
Alpha-oxoisovaleric acid	biospider
Butanoic acid, 3-methyl-2-oxo-	biospider
FEMA 3869	db_source
KIV	biospider
α-keto-isovalerate	Generator
α-keto-isovaleric acid	Generator
α-ketovaline	Generator
α-oxo-β-methylbutyricacid	Generator
α-oxoisovalerate	Generator
α-oxoisovaleric acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	30.2 g/L	ALOGPS
logP	0.49	ALOGPS
logP	1.31	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	3.37	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	2	ChemAxon
Refractivity	27.19 m³·mol⁻¹	ChemAxon
Polarizability	11.04 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

C5H8O3

IUPAC name

3-methyl-2-oxobutanoic acid

InChI Identifier

InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)

InChI Key

QHKABHOOEWYVLI-UHFFFAOYSA-N

Isomeric SMILES

CC(C)C(=O)C(O)=O

Average Molecular Weight

116.1152

Monoisotopic Molecular Weight

116.047344122

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:16530 )
Branched fatty acids (C00141 )
Branched fatty acids (LMFA01020274 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Indirect biological role:

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 51.72%; H 6.94%; O 41.34%	DFC
Melting Point	Mp 31°	DFC
Boiling Point	Bp 170.5°	DFC
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-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9500000000-ff936b879a69b5d118f8	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-8920000000-e37b37d64d43dcf763f0	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-9400000000-e3995acc4818a98d0f48	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-0f79-9720000000-5d89487273e44ea61a68	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9700000000-209c737dcac7df2b198c	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0f79-5920000000-759a2f01b4f52767ade2	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9500000000-ff936b879a69b5d118f8	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-8920000000-e37b37d64d43dcf763f0	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9400000000-e3995acc4818a98d0f48	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0f79-9720000000-5d89487273e44ea61a68	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-7900000000-7e325567183fb56996d5	Spectrum
GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0ufr-0930000000-be90b06add7135b4a539	Spectrum
Predicted GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9000000000-52f9d8fc8386e4c512fe	Spectrum
Predicted GC-MS	3-Methyl-2-oxobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9600000000-52aefdc997dac92c8459	Spectrum
Predicted GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Methyl-2-oxobutanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Methyl-2-oxobutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Methyl-2-oxobutanoic acid, 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)	splash10-000i-9000000000-10ab58a33e9ca7dbace0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-ad51ff01c94b6046ad64	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-9993174a7b1801b90ddb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00xr-9500000000-293818b81e0879b6feb2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-75058f27a2178b9cf121	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-4c20af39e8ee009d5278	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-9993174a7b1801b90ddb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00xr-9500000000-1a58c6a6b4f5477dabdd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-75058f27a2178b9cf121	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-cc4465a47e663be66df5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00di-9100000000-19511890852fce513a02	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9300000000-30d3bdfb6d38dbb8e101	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9000000000-879b6502ff380673b776	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0159-9800000000-0cf4d3a0e7b3356995c6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014o-9900000000-f35430a2eaea0d81df32	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-9400000000-21f8c3fae79161c82099	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-5f25e41413738bb6b5d7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-801af00dea93fcfd637d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-8900000000-5185c7dfc72c25069904	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-9200000000-7e2a275a65197f96f5d7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0600-9000000000-0013e0ff06f9896a1337	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-6900000000-7f00871b074cbd9a42e6	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06di-9400000000-6d56778068e11e4f8e85	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-b445e7fc67a8ff2bd3ba	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-9000000000-733fb7227d2d053b112f	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

CHEMBL146554

KEGG Compound ID

C00141

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16530

Phenol-Explorer ID

Not Available

DrugBank ID

DB04074

HMDB ID

HMDB00019

CRC / DFC (Dictionary of Food Compounds) ID

HFL26-U:HFL26-U

EAFUS ID

2433

Dr. Duke ID

Not Available

BIGG ID

34011

KNApSAcK ID

C00007623

HET ID

KIV

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1047091

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
Pyruvate dehydrogenase E1 component subunit beta, mitochondrial	PDHB	P11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	PDHA1	P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial	PDHA2	P29803
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	BCKDHB	P21953
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial	DLAT	P10515