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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8O3S
Molecular Weight 148.18
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-(METHYLTHIO)-2-OXOBUTANOIC ACID

SMILES

CSCCC(=O)C(O)=O

InChI

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

HIDE SMILES / InChI

Molecular Formula C5H8O3S
Molecular Weight 148.18
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Understanding the physiology of Lactobacillus plantarum at zero growth.
2010-09-21
Therapeutic targeting of C-terminal binding protein in human cancer.
2010-09-15
Incapacitating CtBP to kill cancer.
2010-09-15
Genome-scale metabolic reconstruction and in silico analysis of methylotrophic yeast Pichia pastoris for strain improvement.
2010-07-01
Peroxyl radical scavenging capacity of extracts and isolated components from selected medicinal plants.
2010-06
Abscisic acid-induced resistance against the brown spot pathogen Cochliobolus miyabeanus in rice involves MAP kinase-mediated repression of ethylene signaling.
2010-04
Methionine metabolism in piglets Fed DL-methionine or its hydroxy analogue was affected by distribution of enzymes oxidizing these sources to keto-methionine.
2010-02-10
Activation of mutant enzyme function in vivo by proteasome inhibitors and treatments that induce Hsp70.
2010-01
Potential for development of an Escherichia coli-based biosensor for assessing bioavailable methionine: a review.
2010
Metabolic characteristics and importance of the universal methionine salvage pathway recycling methionine from 5'-methylthioadenosine.
2009-12
1+1 = 3: a fusion of 2 enzymes in the methionine salvage pathway of Tetrahymena thermophila creates a trifunctional enzyme that catalyzes 3 steps in the pathway.
2009-10
A mediator of Rho-dependent invasion moonlights as a methionine salvage enzyme.
2009-10
Arabidopsis thaliana encodes a bacterial-type heterodimeric isopropylmalate isomerase involved in both Leu biosynthesis and the Met chain elongation pathway of glucosinolate formation.
2009-10
Truffles regulate plant root morphogenesis via the production of auxin and ethylene.
2009-08
Ethyl 2-[(2,6-dimethyl-phen-yl)hydrazono]-3-oxobutanoate.
2009-06-10
Ethyl 2-[(4-chloro-phen-yl)hydrazono]-3-oxobutanoate.
2009-04-10
Methionine-derived metabolites in apoptosis: therapeutic opportunities for inhibitors of their metabolism in chemoresistant cancer cells.
2009
A complete inventory of all enzymes in the eukaryotic methionine salvage pathway.
2008-08
Arabidopsis branched-chain aminotransferase 3 functions in both amino acid and glucosinolate biosynthesis.
2008-03
Characterization of metal binding in the active sites of acireductone dioxygenase isoforms from Klebsiella ATCC 8724.
2008-02-26
The hidden universal distribution of amino acid biosynthetic networks: a genomic perspective on their origins and evolution.
2008
Systems analysis of metabolism in the pathogenic trypanosomatid Leishmania major.
2008
Production of the apoptotic cellular mediator 4-Methylthio-2-oxobutyric acid by using an enzymatic stirred tank reactor with in situ product removal.
2007-12-21
Biotransformation of D-methionine into L-methionine in the cascade of four enzymes.
2007-12-01
Structure of Arabidopsis thaliana 5-methylthioribose kinase reveals a more occluded active site than its bacterial homolog.
2007-10-25
Simultaneous determination of ketoacids and dicarbonyl compounds, key Maillard intermediates on the generation of aged wine aroma.
2007-06
Two Arabidopsis genes (IPMS1 and IPMS2) encode isopropylmalate synthase, the branchpoint step in the biosynthesis of leucine.
2007-02
2-Keto-4-methylthiobutyrate, an intermediate in the methionine salvage pathway, is a good substrate for CtBP1.
2007-01-26
Reduction potential tuning of the blue copper center in Pseudomonas aeruginosa azurin by the axial methionine as probed by unnatural amino acids.
2006-12-13
Branched-chain aminotransferase4 is part of the chain elongation pathway in the biosynthesis of methionine-derived glucosinolates in Arabidopsis.
2006-10
The methionine salvage pathway compound 4-methylthio-2-oxobutanate causes apoptosis independent of down-regulation of ornithine decarboxylase.
2006-09-28
[Effect of substrate-dependent microbialy produced ethylene on plant growth].
2006-06-09
Methionine catabolism in Saccharomyces cerevisiae.
2006-01
Radical scavenging and anti-inflammatory properties of STW 5 (Iberogast) and its components.
2006
The mitochondrial branched-chain aminotransferase (AtBCAT-1) is capable to initiate degradation of leucine, isoleucine and valine in almost all tissues in Arabidopsis thaliana.
2005-01
Antioxidants and total oxyradical scavenging capacity during grass shrimp, Palaemonetes pugio, embryogenesis.
2004-12
Branched-chain amino acid aminotransferase and methionine formation in Mycobacterium tuberculosis.
2004-10-07
Analogs of 1-phosphonooxy-2,2-dihydroxy-3-oxo-5-(methylthio)pentane, an acyclic intermediate in the methionine salvage pathway: a new preparation and characterization of activity with E1 enolase/phosphatase from Klebsiella oxytoca.
2004-07-15
4-methylthio 2-oxobutanoate transaminase: a specific target for antiproliferative agents.
2004-04
Glucosinolate biosynthesis: demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa.
2004-04
Bacterial variations on the methionine salvage pathway.
2004-03-04
Kinetics and effects of trace elements and electron complexes on 2-keto-4-methylthiobutyric acid-dependent biosynthesis of ethylene in soil.
2004
Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites.
2003-12-12
Catabolism of volatile sulfur compounds precursors by Brevibacterium linens and Geotrichum candidum, two microorganisms of the cheese ecosystem.
2003-11-06
XAS investigation of the structure and function of Ni in acireductone dioxygenase.
2002-05-28
The methionine salvage pathway in Bacillus subtilis.
2002-04-25
Sulfur compound production by Geotrichum candidum from L-methionine: importance of the transamination step.
2001-12-18
A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway.
2001-11
Cysteine conjugate beta-lyase of rat kidney cytosol: characterization, immunocytochemical localization, and correlation with hexachlorobutadiene nephrotoxicity.
1989-04
The occurrence of 4-methylthio-2-hydroxybutyrate in human urine.
1986-04
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:35:36 GMT 2025
Edited
by admin
on Mon Mar 31 17:35:36 GMT 2025
Record UNII
286060413U
Record Status Validated (UNII)
Record Version
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Name Type Language
.ALPHA.-KETOMETHIONINE
Preferred Name English
4-(METHYLTHIO)-2-OXOBUTANOIC ACID
Systematic Name English
.ALPHA.-KETO-.GAMMA.-(METHYLTHIO)BUTYRIC ACID
Systematic Name English
BUTYRIC ACID, .GAMMA.-METHYLMERCAPTO-.ALPHA.-OXO-
Common Name English
.ALPHA.-OXO-.GAMMA.-(METHYLTHIO)-N-BUTYRIC ACID
Common Name English
.ALPHA.-KETO-METHYLTHIOBUTYRIC ACID
Systematic Name English
2-OXO-4-(METHYLTHIO)BUTANOIC ACID
Systematic Name English
4-(METHYLSULFANYL)-2-OXOBUTANOIC ACID
Systematic Name English
BUTANOIC ACID, 4-(METHYLTHIO)-2-OXO-
Common Name English
2-KETO-4-(METHYLTHIO)BUTYRIC ACID
Systematic Name English
.ALPHA.-KETO-4-(METHYLTHIO)BUTYRIC ACID
Systematic Name English
4-(METHYLTHIO)-2-OXOBUTYRIC ACID
Systematic Name English
Code System Code Type Description
CAS
583-92-6
Created by admin on Mon Mar 31 17:35:36 GMT 2025 , Edited by admin on Mon Mar 31 17:35:36 GMT 2025
PRIMARY
EPA CompTox
DTXSID50207027
Created by admin on Mon Mar 31 17:35:36 GMT 2025 , Edited by admin on Mon Mar 31 17:35:36 GMT 2025
PRIMARY
CHEBI
33574
Created by admin on Mon Mar 31 17:35:36 GMT 2025 , Edited by admin on Mon Mar 31 17:35:36 GMT 2025
PRIMARY
PUBCHEM
473
Created by admin on Mon Mar 31 17:35:36 GMT 2025 , Edited by admin on Mon Mar 31 17:35:36 GMT 2025
PRIMARY
DRUG BANK
DB02238
Created by admin on Mon Mar 31 17:35:36 GMT 2025 , Edited by admin on Mon Mar 31 17:35:36 GMT 2025
PRIMARY
FDA UNII
286060413U
Created by admin on Mon Mar 31 17:35:36 GMT 2025 , Edited by admin on Mon Mar 31 17:35:36 GMT 2025
PRIMARY
Related Record Type Details
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