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 30C
177.3
bromide
in 20 mM MES (pH 7.0), at 30C
1657
chloride
in 20 mM MES (pH 7.0), at 30C
0.012
Diethylthiocarbamoyl sulfide
-
-
0.014
dihydroziprasidone
-
liver cytosol fraction, pH 7.4, 37C
0.056
furfuryl thiol
-
-
0.064
H2S
-
-
4.47
Iodide
in 20 mM MES (pH 7.0), at 30C
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, 25C
0.04
Thiocyanate
in 20 mM MES (pH 7.0), at 30C; pH 7.0, 30C, 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, 30C
0.046
thiobenzoic acid
Physcomitrella patens
-
PpSABATH1, pH 7.5, 25C
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, 30C
5616
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00000003
-
liver cytosol fraction, pH 7.4, 37C
0.000822
-
substrate SCN-, 0.5 mM S-adenosyl-L-methionine, pH 7.5, 25C
0.000966
-
substrate SCN-, 0.5 mM S-adenosyl-L-methionine, pH 7.5, 25C
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, 25C
0.1043
substrate iodometane, pH 7.0, 30C
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
-
30C, 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
4C, 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