P. aeruginosa Metabolome Database: 2-Ketobutyric acid (PAMDB000001)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000001

Identification

Name:

2-Ketobutyric acid

Description:

2-Ketobutyric acid (alpha ketobutyric acid) is involved in the metabolism of many amino acids (glycine, cysteine, methionine, valine, leucine, serine, threonine, isoleucine). It also plays a role in propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid can be produced through the lysis of cystathionine (via cystathionine gamma lyase) leading to the production of cysteine and alpha-ketobutyric acid. It is also one of the degradation products of threonine. It can be converted to propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted to succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

α-ketobutyrate
α-ketobutyric acid
α-oxobutyrate
α-oxobutyric acid
2-Keto-butyrate
2-Keto-butyric acid
2-Ketobutanoate
2-Ketobutanoic acid
2-Ketobutyrate
2-Ketobutyric acid
2-OBA
2-Oxo-Butanoate
2-Oxo-Butanoic acid
2-Oxo-Butyrate
2-Oxo-Butyric acid
2-Oxo-N-butyrate
2-Oxo-N-butyric acid
2-Oxobutanoate
2-Oxobutanoic acid
2-Oxobutyrate
2-Oxobutyric acid
3-Methylpyruvate
3-Methylpyruvic acid
A-Keto-N-Butyrate
A-Keto-N-Butyric acid
a-Ketobutrate
a-Ketobutric acid
A-Ketobutyrate
A-Ketobutyric acid
A-Oxo-N-butyrate
A-Oxo-N-butyric acid
A-Oxobutyrate
A-Oxobutyric acid
Alpha-Keto-N-butyrate
Alpha-Keto-N-butyric acid
Alpha-Ketobutrate
Alpha-Ketobutric acid
Alpha-Ketobutyrate
Alpha-Ketobutyric acid
Alpha-Oxo-N-butyrate
Alpha-Oxo-N-butyric acid
Alpha-Oxobutyrate
Alpha-Oxobutyric acid
Methyl-Pyruvate
Methyl-Pyruvic acid
Propionyl-formate
Propionyl-formic acid
α-keto-N-Butyrate
α-keto-N-Butyric acid
α-Ketobutrate
α-Ketobutric acid
α-Ketobutyrate
α-Ketobutyric acid
α-oxo-N-Butyrate
α-oxo-N-Butyric acid
α-Oxobutyrate
α-Oxobutyric acid

Chemical Formula:

C₄H₆O₃

Average Molecular Weight:

102.0886

Monoisotopic Molecular Weight:

102.031694058

InChI Key:

TYEYBOSBBBHJIV-UHFFFAOYSA-N

InChI:

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

CAS number:

600-18-0

IUPAC Name:

2-oxobutanoic acid

Traditional IUPAC Name:

2-oxobutanoic acid

SMILES:

CCC(=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound 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
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 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

33°C [Suante, H.; Oxidation Communications 2004, V27(2), P344-348]

Experimental Properties:

Property	Value	Source
Water Solubility:	119 mg/mL [HMP experimental]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	79.2 mg/mL	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

C5-Branched dibasic acid metabolism pae00660
Cysteine and methionine metabolism pae00270
Glycine, serine and threonine metabolism pae00260
Metabolic pathways pae01100
Propanoate metabolism pae00640
Valine, leucine and isoleucine biosynthesis pae00290

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-014s-1910000000-d01bcd7b41fdcc634eea	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9200000000-3b3816ffee5771215904	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-6910000000-5b264d5f7e53f3e80b12	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-6950000000-db7f6a0f03a8cce59bae	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0pb9-9600000000-53ebb7164f74d7d92a4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0zfr-5900000000-1db864754705beb79b55	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0udi-9800000000-5ba5b9ede5b1bc389b87	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-bfdcad5bc3ed586bdede	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9i-9400000000-0061f4635858d851f127	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-b943445194fb5f8e3a0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-bc5920b9bd140be6b06d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-f7dfb4554f0b9e1499c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-9200000000-e54106ad5bf45a9f072c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-7bbba57578cf720974e3	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Sprague CL, Elfarra AA: Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene. Drug Metab Dispos. 2003 Aug;31(8):986-92. Pubmed: 12867486
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Yaegaki K, Sanada K: Biochemical and clinical factors influencing oral malodor in periodontal patients. J Periodontol. 1992 Sep;63(9):783-9. Pubmed: 1474480
Yaegaki K, Sanada K: Effects of a two-phase oil-water mouthwash on halitosis. Clin Prev Dent. 1992 Jan-Feb;14(1):5-9. Pubmed: 1499240
Yang W, Roth KS: Defect in alpha-ketobutyrate metabolism: a new inborn error. Clin Chim Acta. 1985 Jan 30;145(2):173-82. Pubmed: 3918815

Synthesis Reference:

Figge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl. (2006), 31pp.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16763
HMDB ID	HMDB00005
Pubchem Compound ID	58
Kegg ID	C00109
ChemSpider ID	57
Wikipedia	Alpha-ketobutyric_acid
BioCyc ID	2-OXOBUTANOATE
EcoCyc ID	2-OXOBUTANOATE
Ligand Expo	2KT

2-Ketobutyric acid (PAMDB000001)

Structure for 2-Ketobutyric acid (PAMDB000001)