Showing Compound 2-Oxobutanoic acid (FDB003359)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:46 UTC

Update date

2020-09-17 15:38:09 UTC

Primary ID

FDB003359

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Oxobutanoic acid

Description

2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, 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. 2-Ketobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Ketobutyric acid exists in all living species, ranging from bacteria to humans. Within humans, 2-ketobutyric acid participates in a number of enzymatic reactions. In particular, 2-ketobutyric acid can be biosynthesized from L-threonine; which is mediated by the enzyme L-serine dehydratase/l-threonine deaminase. In addition, 2-ketobutyric acid and coenzyme A can be converted into propionyl-CoA; which is mediated by the enzyme branched-chain alpha-keto dehydrogenase complex. In humans, 2-ketobutyric acid is involved in threonine and 2-oxobutanoate degradation. Outside of the human body, 2-Ketobutyric acid has been detected, but not quantified in, several different foods, such as black crowberries, lima beans, lettuces, oxheart cabbages, and grass pea. This could make 2-ketobutyric acid a potential biomarker for the consumption of these foods. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.

CAS Number

600-18-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Ketobutanoic acid	ChEBI
2-Oxobutyric acid	ChEBI
3-Methyl pyruvic acid	ChEBI
alpha-Ketobutyrate	ChEBI
alpha-Ketobutyric acid	ChEBI
alpha-oxo-N-Butyric acid	ChEBI
2-Oxobutyrate	Kegg
2-Oxobutanoic acid	Kegg
2-Ketobutanoate	Generator
3-Methyl pyruvate	Generator
a-Ketobutyrate	Generator
a-Ketobutyric acid	Generator
Α-ketobutyrate	Generator
Α-ketobutyric acid	Generator
a-oxo-N-Butyrate	Generator
a-oxo-N-Butyric acid	Generator
alpha-oxo-N-Butyrate	Generator
Α-oxo-N-butyrate	Generator
Α-oxo-N-butyric acid	Generator
2-Oxobutanoate	Generator
2-Ketobutyrate	Generator
2-oxo-Butanoate	HMDB
2-oxo-Butanoic acid	HMDB
2-oxo-Butyrate	HMDB
2-oxo-Butyric acid	HMDB
2-oxo-N-Butyrate	HMDB
2-oxo-N-Butyric acid	HMDB
3-Methylpyruvate	HMDB
3-Methylpyruvic acid	HMDB
a-Keto-N-butyrate	HMDB
a-Keto-N-butyric acid	HMDB
a-Oxobutyrate	HMDB
a-Oxobutyric acid	HMDB
alpha-Keto-N-butyrate	HMDB
alpha-Keto-N-butyric acid	HMDB
alpha-Ketobutric acid	HMDB
alpha-Oxobutyrate	HMDB
alpha-Oxobutyric acid	HMDB
Methyl-pyruvate	HMDB
Methyl-pyruvic acid	HMDB
Propionyl-formate	HMDB
Propionyl-formic acid	HMDB
alpha-Ketobutyric acid, sodium salt	HMDB
2-Ketobutyric acid	ChEBI
α-keto-n-butyric acid	biospider
α-ketobutric acid	biospider
α-ketobutyric acid	biospider
α-oxo-n-butyric acid	biospider
α-oxobutyrate	biospider
α-oxobutyric acid	biospider
2-keto-butyrate	biospider
2-ketobutyrate	biospider
2-Oxo-Butanoate	biospider
2-Oxo-Butanoic acid	biospider
2-Oxo-n-butyrate	biospider
2-Oxo-n-butyric acid	biospider
3-methyl pyruvic acid	biospider
A-keto-n-butyrate	biospider
A-keto-n-butyric acid	biospider
A-ketobutyrate	biospider
A-ketobutyric acid	biospider
A-oxo-n-butyrate	biospider
A-oxo-n-butyric acid	biospider
A-oxobutyrate	biospider
A-oxobutyric acid	biospider
Alpha-keto-n-butyrate	biospider
Alpha-keto-n-butyric acid	biospider
Alpha-ketobutric acid	biospider
Alpha-ketobutyrate	biospider
Alpha-ketobutyric acid	biospider
Alpha-ketobutyric acid, na	biospider
Alpha-oxo-n-butyrate	biospider
Alpha-oxo-n-butyric acid	biospider
Alpha-oxobutyrate	biospider
Alpha-oxobutyric acid	biospider
Butanoic acid, 2-oxo-	biospider
Butanoic acid, 2-oxo- (9CI)	biospider
Butyric acid, 2-oxo-	biospider
Butyric acid, 2-oxo- (8CI)	biospider
FEMA 3723	db_source
Formic acid, propionyl-	biospider
Ketobutyrate	biospider
Oxobutyrate	biospider
Propionylformic acid	biospider
Pyruvic acid, methyl-	biospider
α-ketobutyrate	Generator
α-ketobutyric acid	Generator
α-oxo-N-butyrate	Generator
α-oxo-N-butyric acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	79.2 g/L	ALOGPS
logP	0.07	ALOGPS
logP	0.77	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	3.19	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	22.62 m³·mol⁻¹	ChemAxon
Polarizability	9.2 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

C4H6O3

IUPAC name

2-oxobutanoic acid

InChI Identifier

InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)

InChI Key

TYEYBOSBBBHJIV-UHFFFAOYSA-N

Isomeric SMILES

CCC(=O)C(O)=O

Average Molecular Weight

102.0886

Monoisotopic Molecular Weight

102.031694058

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

Short-chain keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:30831 )
short-chain fatty acid (CHEBI:30831 )
Oxo fatty acids (C00109 )
Oxo fatty acids (LMFA01060002 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 47.06%; H 5.92%; O 47.02%	DFC
Melting Point	Mp 31-32°	DFC
Boiling Point	Bp12 66°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa1 2.5 (25°)	DFC
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	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-014s-1910000000-d01bcd7b41fdcc634eea	Spectrum
GC-MS	2-Oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-9200000000-3b3816ffee5771215904	Spectrum
GC-MS	2-Oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-6910000000-5b264d5f7e53f3e80b12	Spectrum
GC-MS	2-Oxobutanoic acid, 2 TMS, GC-MS Spectrum	splash10-001i-6950000000-db7f6a0f03a8cce59bae	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0ftb-0920000000-a6c93d8761ef15f7f7d4	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0920000000-406fe70e72dbd9c3f274	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-014s-1910000000-d01bcd7b41fdcc634eea	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-3b3816ffee5771215904	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-6910000000-5b264d5f7e53f3e80b12	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-001i-6950000000-db7f6a0f03a8cce59bae	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-8900000000-97bab6630de4df095a7f	Spectrum
GC-MS	2-Oxobutanoic acid, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-0ebb2354fe3f935fe177	Spectrum
Predicted GC-MS	2-Oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6r-9000000000-32269ef3ef778c482f99	Spectrum
Predicted GC-MS	2-Oxobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adi-9200000000-f92941e9f326d8ccf3e4	Spectrum
Predicted GC-MS	2-Oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxobutanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxobutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	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, Negative (Annotated)	splash10-0pb9-9600000000-53ebb7164f74d7d92a4d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0zfr-5900000000-1db864754705beb79b55	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0udi-9800000000-5ba5b9ede5b1bc389b87	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-bfdcad5bc3ed586bdede	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-bfdcad5bc3ed586bdede	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-0pb9-9600000000-b10635fbec5572d4d084	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0a4i-9100000000-4c5e7d24dca6677e1570	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0a4i-9000000000-ded44cfcbe7960954fdf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 16V, positive	splash10-0a4i-9000000000-1b350be7438b08f1946a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-056r-9000000000-172a175b8b9ebfd5529f	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9i-9400000000-0061f4635858d851f127	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-b943445194fb5f8e3a0f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-bc5920b9bd140be6b06d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-f7dfb4554f0b9e1499c9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-9200000000-e54106ad5bf45a9f072c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-7bbba57578cf720974e3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-ca1ed9c5aadcbdabc2a3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-aced8e004436190f07b7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a3d7ddf227bd6aa91a54	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9700000000-503296025148ec314383	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-933b567955b5de5b1744	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-7d9db52021fefc87a855	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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

CHEMBL171246

KEGG Compound ID

C00109

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16763

Phenol-Explorer ID

Not Available

DrugBank ID

DB04553

HMDB ID

HMDB00005

CRC / DFC (Dictionary of Food Compounds) ID

CWG39-N:CWG39-N

EAFUS ID

1963

Dr. Duke ID

Not Available

BIGG ID

33889

KNApSAcK ID

C00019675

HET ID

2KT

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1037661

SuperScent ID

Not Available

Wikipedia ID

Alpha-ketobutyric_acid

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
Cystathionine gamma-lyase	CTH	P32929
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
2-oxoglutarate dehydrogenase, mitochondrial	OGDH	Q02218
L-serine dehydratase/L-threonine deaminase	SDS	P20132
[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrial	BCKDK	O14874
Serine dehydratase-like	SDSL	Q96GA7
2-oxoglutarate dehydrogenase-like, mitochondrial	OGDHL	Q9ULD0

Pathways

Name	SMPDB Link	KEGG Link
Glycine and Serine Metabolism	SMP00004	map00260
Homocysteine Degradation	SMP00455	Not Available
Methionine Metabolism	SMP00033	map00270
Threonine and 2-Oxobutanoate Degradation	SMP00452	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
brown	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lactonic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.