Information on EC 2.1.1.9 - thiol S-methyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.1.1.9
-
RECOMMENDED NAME
GeneOntology No.
thiol S-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + a thiol = S-adenosyl-L-homocysteine + a methyl thioether
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
-
-
-
-
S-methylation
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
glutathione-mediated detoxification II
-
-
sulfur volatiles biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:thiol S-methyltransferase
H2S and a variety of alkyl, aryl and heterocyclic thiols and hydroxy thiols can act as acceptors.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-81-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
low activity
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2Z)-[(4R)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid + S-adenosyl-L-methionine
(2Z)-[(4R)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-(methylsulfanyl)piperidin-3-ylidene]acetic acid + S-adenosyl-L-homocysteine
show the reaction diagram
-
thiol metabolite H4 of prodrug clopidogrel. The intrinsic clearance value for the S-methylation of metabolite H3 in microsomes is 98.1fold higher than that for H4
-
-
?
(2Z)-[(4S)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid + S-adenosyl-L-methionine
(2Z)-[(4S)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-(methylsulfanyl)piperidin-3-ylidene]acetic acid + S-adenosyl-L-homocysteine
show the reaction diagram
-
thiol metabolite H3 of prodrug clopidogrel. The intrinsic clearance value for the S-methylation of metabolite H3 in microsomes is 98.1fold higher than that for H4
-
-
?
1,3-hexanediol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
1-methylimidazole-2-thiol + S-adenosyl-L-methionine
1-methyl-2-(methylthio)-1H-imidazole + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
2,3-dimercaptopropanol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
2-benzimidazole thiol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
2-mercaptoacetic acid + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
2-mercaptobenzothiazole + S-adenosyl-L-methionine
S-methyl-2-mercaptobenzothiazole + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
?
2-mercaptoethanol + S-adenosyl-L-methionine
S-methyl-2-mercaptoethanol + S-adenosyl-L-homocysteine
show the reaction diagram
2-mercaptopropanoic acid + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
2-mercaptopropionic acid + S-adenosyl-L-methionine
S-methyl-2-mercaptopropionic acid + S-adenosyl-L-homocysteine
show the reaction diagram
2-thioacetanilide + S-adenosyl-L-methionine
S-methyl-2-thioacetanilide + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
3-mercaptohexan-1-ol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
3-mercaptopropanoic acid + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
3-mercaptopropionic acid methyl ester + S-adenosyl-L-methionine
S-methyl-3-mercaptopropionic acid methyl ester + S-adenosyl-L-homocysteine
show the reaction diagram
4,4'-thiobisbenzenethiol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
4-chlorothiophenol + S-adenosyl-L-methionine
4-chloro-S-methylphenylmercaptan + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
4-nitrothiophenol + S-adenosyl-L-methionine
4-nitro-S-methylphenylmercaptan + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
6-mercaptohexan-1-ol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
6-propyl-2-thiouracil + S-adenosyl-L-methionine
6-propyl-S-methyl-2-thiouracil + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
6-thiopurine + S-adenosyl-L-methionine
S-methyl-6-thiopurine + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
?
benzene thiol + S-adenosyl-L-methionine
methyl phenyl sulfide + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
benzylmercaptan + S-adenosyl-L-methionine
benzylmethylsulfide + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
?
bisulfide + S-adenosyl-L-methionine
methanethiol + S-adenosyl-L-homocysteine
show the reaction diagram
highest activity
-
-
?
diethylthiocarbamoyl sulfide + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
dihydroziprasidone + S-adenosyl-L-methionine
S-methyldihydroziprasidone + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
dithiothreitol + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
dithiothreitol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
ethanethioic S-acid + S-adenosyl-L-methionine
S-methylethanethioate + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
furfuryl thiol + S-adenosyl-L-methionine
2-[(methylsulfanyl)methyl]furan + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
furfuryl thiol + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
guaiacol + S-adenosyl-L-methionine
1,2-dimethoxybenzene + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
H2S + S-adenosyl-L-methionine
methanethiol + S-adenosyl-L-homocysteine
show the reaction diagram
L-cysteine methyl ester + S-adenosyl-L-methionine
S-methyl-L-cysteine methyl ester + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
mercaptoacetic acid + S-adenosyl-L-methionine
S-methylmercaptoacetic acid + S-adenosyl-L-homocysteine
show the reaction diagram
methylmercaptan + S-adenosyl-L-methionine
dimethylsulfide + S-adenosyl-L-homocysteine
show the reaction diagram
-
i.e. methanethiol
-
-
?
N-acetyl-L-cysteine + S-adenosyl-L-methionine
N-acetyl-S-methyl-L-cysteine + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
O-methylmercaptoethanol + S-adenosyl-L-methionine
2-methoxy-S-methyl-1-thioethane + S-adenosyl-L-homocysteine
show the reaction diagram
pentachlorobenzenethiol + S-adenosyl-L-methionine
1,2,3,4,5-pentachloro-6-(methylthio)benzene + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
phenol + S-adenosyl-L-methionine
methoxybenzene + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
phenyl sulfide + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
S-3'-deoxyadenosyl-L-methionine + 2-mercaptoethanol
S-3'-deoxyadenosyl-L-homocysteine + S-methyl-2-mercaptoethanol
show the reaction diagram
-
-
-
-
?
S-3-deazaadenosyl-L-methionine + 2-mercaptoethanol
S-3-deazaadenosyl-L-homocysteine + S-methyl-2-mercaptoethanol
show the reaction diagram
-
-
-
-
?
S-8-azaadenosyl-L-methionine + 2-mercaptoethanol
S-8-azaadenosyl-L-homocysteine + S-methyl-2-mercaptoethanol
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + a thiol
S-adenosyl-L-homocysteine + a thioether
show the reaction diagram
S-adenosyl-L-methionine + bromide
S-adenosyl-L-homocysteine + bromomethane
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + chloride
S-adenosyl-L-homocysteine + chloromethane
show the reaction diagram
very low activity
-
-
?
S-adenosyl-L-methionine + HS-
?
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + HS-
S-adenosyl-L-homocysteine + CH3SH
show the reaction diagram
S-adenosyl-L-methionine + iodide
S-adenosyl-L-homocysteine + iodomethane
show the reaction diagram
-
-
-
?
S-aristeromycinyl-L-methionine + 2-mercaptoethanol
S-aristeromycinyl-L-homocysteine + S-methyl-2-mercaptoethanol
show the reaction diagram
-
-
-
-
?
S-N6-methyladenosyl-L-methionine + 2-mercaptoethanol
S-N6-methyladenosyl-L-homocysteine + S-methyl-2-mercaptoethanol
show the reaction diagram
-
-
-
-
?
S-tubercidinyl-L-methionine + 2-mercaptoethanol
S-tubercidinyl-L-homocysteine + S-methyl-2-mercaptoethanol
show the reaction diagram
-
-
-
-
?
SH- + S-adenosyl-L-methionine
CH3SH + S-adenosyl-L-homocysteine
show the reaction diagram
thiobenzoic acid + S-adenosyl-L-methionine
methylthiobenzoate + S-adenosyl-L-homocysteine + H+
show the reaction diagram
-
-
-
-
?
thiocyanate + S-adenosyl-L-methionine
?
show the reaction diagram
thiocyanate + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
thiocyanate + S-adenosyl-L-methionine
methyl thiocyanate + S-adenosyl-L-homocysteine
show the reaction diagram
thiophenol + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
thiophenol + S-adenosyl-L-methionine
S-methylphenylmercaptan + S-adenosyl-L-homocysteine
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + a thiol
S-adenosyl-L-homocysteine + a thioether
show the reaction diagram
thiocyanate + S-adenosyl-L-methionine
?
show the reaction diagram
Q0WP12
AtHOL1 is involved in glucosinolate metabolism and defense against phytopathogens. CH3Cl synthesized by AtHOL1 could be considered a byproduct of NCS- metabolism
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K+
-
5 mM chloride salt, stimulates PpSABATH1 activity by 70%
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,3-dichloro-alpha-methylbenzylamine
-
in liver S-9 fraction 90% inhibition at 1 mM
2,3-dichloromethyl benzylamine
-
-
-
Ca2+
-
5 mM chloride salt, mild inhibitory effect, <25%, PpSABATH1
Cu2+
-
5 mM chloride salt, strong inhibitory effect, 50-100%, PpSABATH1
cystine
-
55% inhibition at 10 mM
Fe2+
-
5 mM chloride salt, strong inhibitory effect, 50-100%, PpSABATH1
Fe3+
-
5 mM chloride salt, strong inhibitory effect, 50-100%, PpSABATH1
iodoacetamide
-
55% inhibition at 10 mM
Mg2+
-
5 mM chloride salt, strong inhibitory effect, 50-100%, PpSABATH1
Mn2+
-
5 mM chloride salt, strong inhibitory effect, 50-100%, PpSABATH1
N-ethylmaleimide
p-chloromercuribenzoate
p-hydroxymercuribenzoic acid
-
95% inhibition at 10 mM, reversed in presence of 20 mM Cys
S-3-deazaadenosyl-L-homocysteine
-
-
S-adenosyl-L-homocysteine
-
-
S-Tubercidinyl-L-homocysteine
-
-
SKF 525A
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.4
1-methylimidazol-2-thiol
-
-
1.6
2,3-Dimercaptopropanol
-
-
0.11
2-Benzimidazole thiol
-
-
2.37 - 8.1
2-mercaptoethanol
1.2
2-mercaptopropionic acid
-
-
0.043
2-Thioacetanilide
-
-
4.7
3-mercaptopropionic acid methyl ester
-
-
0.00054
4-Chlorothiophenol
-
-
0.0028
4-Nitrothiophenol
-
-
1
6-Propyl-2-thiouracil
-
-
0.218
benzene thiol
-
-
12.24
bisulfide
in 20 mM MES (pH 7.0), at 30°C
177.3
bromide
in 20 mM MES (pH 7.0), at 30°C
1657
chloride
in 20 mM MES (pH 7.0), at 30°C
0.012
Diethylthiocarbamoyl sulfide
-
-
0.014
dihydroziprasidone
-
liver cytosol fraction, pH 7.4, 37°C
0.056
furfuryl thiol
-
-
0.064
H2S
-
-
4.47
Iodide
in 20 mM MES (pH 7.0), at 30°C
0.21
L-cysteine methyl ester
-
-
0.24
methanethiol
-
-
0.4
N-acetyl-L-cysteine
-
-
0.099 - 0.141
NCS-
0.082
Pentachlorobenzenethiol
-
-
0.0011
phenyl sulfide
-
-
0.12
S-3'-Deoxyadenosyl-L-methionine
-
-
0.224
S-3-Deazaadenosyl-L-methionine
-
-
0.719
S-8-Azaadenosyl-L-methionine
-
-
0.096 - 94.2
S-adenosyl-L-methionine
0.06
S-Aristeromycinyl-L-methionine
-
-
1.017
S-N6-Methyladenosyl-L-methionine
-
-
0.154
S-Tubercidinyl-L-methionine
-
-
0.145 - 7.9
SCN-
9.9 - 12.24
SH-
83.2
thiobenzoic acid
-
PpSABATH1, pH 7.5, 25°C
0.04
Thiocyanate
in 20 mM MES (pH 7.0), at 30°C; pH 7.0, 30°C, purified recombinant enzyme
0.19
thioglycolic acid
-
-
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000372 - 0.0102
SCN-
0.0381
SH-
Phaeodactylum tricornutum
B7FWR0
pH 7.0, 30°C
0.046
thiobenzoic acid
Physcomitrella patens
-
PpSABATH1, pH 7.5, 25°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00129 - 0.00308
SCN-
1032
0.00385
SH-
Phaeodactylum tricornutum
B7FWR0
pH 7.0, 30°C
5616
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00000003
-
liver cytosol fraction, pH 7.4, 37°C
0.000822
-
substrate SCN-, 0.5 mM S-adenosyl-L-methionine, pH 7.5, 25°C
0.000966
-
substrate SCN-, 0.5 mM S-adenosyl-L-methionine, pH 7.5, 25°C
0.0434
-
substrate NCS-, V23C mutant protein, pH not specified in the publication, temperature not specified in the publication
0.0436
-
substrate NCS-, wild type protein, pH not specified in the publication, temperature not specified in the publication
0.046
-
substrate NCS-, Y172F mutant protein, pH not specified in the publication, temperature not specified in the publication
0.0696
-
with thiobenzoic acid as substrate, pH 7.5, 25°C
0.1043
substrate iodometane, pH 7.0, 30°C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
50% activity at pH 6.0 or pH 8.5
7.2 - 7.6
-
high-affinity form
7.2 - 8.1
-
high-affinity form
7.8 - 9
-
S-methylation of 2-mercaptoethanol
8.8
-
low-affinity form
9 - 9.3
-
with furfuryl thiol as substrate
9.2
-
low-affinity form
9.5
-
reaction rate increases with pH to at least pH 9.5
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.2 - 6.4
-
form II
5.8 - 7.8
-
form III
6.5 - 11
-
with furfuryl thiol as substrate
6.6 - 8.6
-
about 50% of maximum activity at pH 6.6 and pH 8.6
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
-
with furfuryl thiol as substrate
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10 - 30
-
with furfuryl thiol as substrate
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
rice expression profile database
Manually annotated by BRENDA team
-
rice expression profile database
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
in extracts of liver, kidney, intestine and spleen
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
21000
-
gel filtration
26200
-
x * 26200, predicted molecular mass
27300
-
x * 27300, predicted molecular mass
29000
SDS-PAGE
34000
1 * 34000, SDS-PAGE, His-tagged protein
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
co-crystallized with S-adenosyl-L-homocysteine
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
70% of its maximal enzyme activity, PpSABATH1
723371
7.9
-
30°C, absence of nucleotide substrate, half-life: less than 1 min
441584
8
-
54% of its maximal enzyme activity, PpSABATH1
723371
9
-
33% of its maximal enzyme activity, PpSABATH1
723371
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10
-
loss of 20% of enzyme activity when incubated for 30 min, PpSABATH1
20
-
loss of 57% of enzyme activity when incubated for 30 min, PpSABATH1
30
-
loss of 64% of enzyme activity when incubated for 30 min, PpSABATH1
50
-
loss of 100% of enzyme activity when incubated for 30 min, PpSABATH1
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
freezing destroys activity
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 140 mM NaCl, 10 mM Tris-chloride, pH 7.4, half-life: 4 days, best conditions of storage
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE-Toyopearl 650 M column chromatography and Ni-Sepharose column chromatography; partial
glutathione-Sepharose, GST part removed
-
immobilized metal ion affinity chromatography (Ni2+)
immobilized metal ion affinity chromatography, His-tag remove
-
partial
purification of recombinant His-tagged PpSABATH1 protein
-
to near homogeneity by Ni-chelation affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli; expressed in Escherichia coli BL21(DE3) cells
GST-fusion protein expressed in Escherichia coli BL21(DE3)
-
His-tagged protein expressed in Escherichia coli BL21(DE3), together with chaperone-coding genes (plasmid pG-KJE8)
His-tagged protein expressed in Escherichia coli Rosetta II (DE3)
-
PpSABATH1 full-length cDNA cloned into the pET100/DTOPO vector in Escherichia coli
-
subcloned for expression of a His-tagged recombinant protein in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
2 h after treatment with 250 microM and 500 microM thiobenzoic acid expression of PpSABATH1 is down-regulated
-
24 h after treatment, expression of PpSABATH1 is up-regulated by eight-fold in plants treated with 250 microM thiobenzoic acid and 16-fold in plants treated with 500 microM thiobenzoic acid
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
V23C
-
not conserved active site residue, slightly improved activity, lowered stability
Y172F
-
reduced efficiency with Cl-
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
additional information
-
a few changes in key residues are sufficient to convert an OMT into a S-methyltransferase