P. aeruginosa Metabolome Database: 2-Oxo-4-methylthiobutanoic acid (PAMDB000418)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000418

Identification

Name:

2-Oxo-4-methylthiobutanoic acid

Description:

2-oxo-4-methylthiobutanoic acid is the direct precursor of methional. It is an intermediate of cysteine and methionine metabolism. It is converted to L-methionine via tyrosine aminotransferase. (KEGG)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

α-keto-γ-methylthiobutyrate
α-keto-γ-methylthiobutyric acid
α-keto-4-methylthiobutyrate
α-keto-4-methylthiobutyric acid
α-ketomethiobutyrate
α-ketomethiobutyric acid
2-Keto-4-methylthiobutanoate
2-Keto-4-methylthiobutanoic acid
2-Keto-4-methylthiobutyrate
2-Keto-4-methylthiobutyric acid
2-Keto-methyl-thio-butyrate
2-Keto-methyl-thio-butyric acid
2-Ketomethiobutyrate
2-Ketomethiobutyric acid
2-Oxo-4-methylthiobutanoate
2-Oxo-4-methylthiobutanoic acid
2-Oxomethionine
4-Methylthio-2-ketobutanoate
4-Methylthio-2-ketobutanoic acid
4-Methylthio-2-ketobutyrate
4-Methylthio-2-ketobutyric acid
4-Methylthio-2-oxobutanoate
4-Methylthio-2-oxobutanoic acid
4-Methylthio-2-oxobutyrate
4-Methylthio-2-oxobutyric acid
a-keto-4-Methylthiobutyrate
a-keto-4-Methylthiobutyric acid
a-keto-g-Methylthiobutyrate
a-keto-g-Methylthiobutyric acid
a-keto-Methiolbutyrate
a-keto-Methiolbutyric acid
a-Ketomethiobutyrate
a-Ketomethiobutyric acid
Alpha-Keto-4-methylthiobutyrate
Alpha-Keto-4-methylthiobutyric acid
Alpha-Keto-gamma-methylthiobutyrate
Alpha-Keto-gamma-methylthiobutyric acid
alpha-keto-Methiolbutyrate
Alpha-Keto-methiolbutyric acid
Alpha-Ketomethiobutyrate
Alpha-Ketomethiobutyric acid
Keto-4-methylthiobutyrate
Keto-4-methylthiobutyric acid
Ketomethiobutyrate
Ketomethiobutyric acid
KMTB
Methylthiobutyrate
Methylthiobutyric acid
α-keto-4-Methylthiobutyrate
α-keto-4-Methylthiobutyric acid
α-keto-Methiolbutyrate
α-keto-Methiolbutyric acid
α-keto-γ-Methylthiobutyrate
α-keto-γ-Methylthiobutyric acid
α-Ketomethiobutyrate
α-Ketomethiobutyric acid

Chemical Formula:

C₅H₈O₃S

Average Molecular Weight:

148.18

Monoisotopic Molecular Weight:

148.019414812

InChI Key:

SXFSQZDSUWACKX-UHFFFAOYSA-N

InChI:

InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)

CAS number:

583-92-6

IUPAC Name:

4-(methylsulfanyl)-2-oxobutanoic acid

Traditional IUPAC Name:

2-oxo-4-thiomethylbutyric acid

SMILES:

CSCCC(=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Thia fatty acids

Alternative Parents

Substituents

Thia fatty acid
Short-chain keto acid
Keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfur-containing carboxylic acid (CHEBI:33574 )
2-oxo monocarboxylic acid (CHEBI:33574 )
Oxo fatty acids (C01180 )
Oxo fatty acids (LMFA01060170 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	7.44 mg/mL	ALOGPS
logP	-0.07	ALOGPS
logP	1.12	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.3	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	4	ChemAxon
Refractivity	35.07 m³·mol^-1	ChemAxon
Polarizability	14.21 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:

2-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-Ketoglutarate
2-Oxo-4-methylthiobutanoic acid + hydroxyl radical > Hydrogen ion + ethylene + methanethiol + Carbon dioxide
L-Methionine + a 2-oxo carboxylate 2-Oxo-4-methylthiobutanoic acid + a standard α amino acid
L-Methionine + a 2-oxo acid > 2-Oxo-4-methylthiobutanoic acid + an L-amino acid

Pathways:

Cysteine and methionine metabolism pae00270

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0f79-9620000000-a37f1649aaa00fe355f6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0uyr-7940000000-be5c411217da093f2c8a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f8a-1900000000-ed36a40a48bf904312f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zir-9700000000-7bbe813aa31ceba0b525	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9100000000-89ba14ad10b374e8daab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9200000000-b9179ec180a89222c147	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9100000000-63d77e1e6b7bea5353fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-31b5d7804293c55c928e	View in MoNA

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
Martensson J: The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. Anal Biochem. 1986 Apr;154(1):43-9. Pubmed: 3706736
Quash G, Roch AM, Chantepie J, Michal Y, Fournet G, Dumontet C: Methional derived from 4-methylthio-2-oxobutanoate is a cellular mediator of apoptosis in BAF3 lymphoid cells. Biochem J. 1995 Feb 1;305 ( Pt 3):1017-25. Pubmed: 7848263
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Brodelius, P.; Hagerdal, B.; Mosbach, K. Immobilized whole cells of the yeast Trigonopsis variabilis containing D-amino acid oxidase for the production of a-keto acids. Enzyme Engineering (1980), 5 383-7.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16723
HMDB ID	HMDB01553
Pubchem Compound ID	473
Kegg ID	C01180
ChemSpider ID	460
Wikipedia ID	Not Available
BioCyc ID	CPD-479
EcoCyc ID	CPD-479
Ligand Expo	KMT

2-Oxo-4-methylthiobutanoic acid (PAMDB000418)

Structure for 2-Oxo-4-methylthiobutanoic acid (PAMDB000418)