Information on EC 2.1.1.25 - phenol O-methyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.1.1.25
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RECOMMENDED NAME
GeneOntology No.
phenol O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + phenol = S-adenosyl-L-homocysteine + anisole
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:phenol O-methyltransferase
Acts on a wide variety of simple alkyl-, methoxy- and halo-phenols.
CAS REGISTRY NUMBER
COMMENTARY hide
37256-94-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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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
S-adenosyl-L-methionine + 2,4-dibromophenol
S-adenosyl-L-homocysteine + 2,4-dibromo-1-methoxybenzene
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 2,4-dichlorophenol
S-adenosyl-L-homocysteine + 2,4-dichloro-1-methoxybenzene
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxy-3,5-dimethoxyacetophenone
S-adenosyl-L-homocysteine + 3,4,5-trimethoxyacetophenone
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxy-3,5-dimethoxybenzaldehyde
S-adenosyl-L-homocysteine + 3,4,5-trimethoxybenzaldehyde
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 4-hydroxy-3,5-dimethoxybenzoic acid
S-adenosyl-L-homocysteine + 3,4,5-trimethoxybenzoic acid
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 4-hydroxy-3-methoxyacetophenone
S-adenosyl-L-homocysteine + 3,4-dimethoxyacetophenone
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxy-3-methoxybenzaldehyde
S-adenosyl-L-homocysteine + 3,4-dimethoxybenzaldehyde
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxy-3-methoxybenzoic acid
S-adenosyl-L-homocysteine + 3,4-dimethoxybenzoic acid
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + acetaminophen
S-adenosyl-L-homocysteine + N-(4-methoxyphenyl)-acetamide
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + m-bromophenol
S-adenosyl-L-homocysteine + m-bromoanisole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + m-chlorophenol
S-adenosyl-L-homocysteine + m-chloroanisole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + m-methoxyphenol
S-adenosyl-L-homocysteine + 1,3-dimethoxybenzene
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + m-nitrophenol
S-adenosyl-L-homocysteine + m-nitroanisole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + o-chlorophenol
S-adenosyl-L-homocysteine + o-chloroanisole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + o-methoxyphenol
S-adenosyl-L-homocysteine + veratrole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + o-methylphenol
S-adenosyl-L-homocysteine + o-methylanisole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + p-chlorophenol
S-adenosyl-L-homocysteine + p-chloroanisole
show the reaction diagram
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-
-
?
S-adenosyl-L-methionine + p-ethylphenol
S-adenosyl-L-homocysteine + p-ethylanisole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + p-hydroxyacetanilide
S-adenosyl-L-homocysteine + p-methoxyacetanilide
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + p-methoxyphenol
S-adenosyl-L-homocysteine + 1,4-dimethoxybenzene
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + p-methylphenol
S-adenosyl-L-homocysteine + p-methylanisole
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + phenol
S-adenosyl-L-homocysteine + anisole
show the reaction diagram
additional information
?
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3-methoxy- and 3,5-dimethoxy-substituted 4-hydroxy-benzaldehydes, -benzoic acids, and -acetophenones are the preferred substrates. The corresponding 3,4-dihydroxy compounds are methylated relatively slowly, while the 3-hydroxy-4-methoxy compounds are almost inactive as substrates. Substituents in both the 2 and 4 positions relative to the hydroxyl group appear to be essential for significant enzyme attack of a substrate. Xenobiotic compounds such as 2,4-dichlorophenol and 2,4-dibromophenol are methylated almost as readily as 4-hydroxy-3-methoxyacetophenone. No substrates: homovanillic acid, caffeic acid, ferulic acid
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ag+
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0.1 mM, no resiudal activity
Cu2+
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0.1 mM, no resiudal activity
Hg2+
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0.1 mM, no resiudal activity
Mg2+
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10 mM, 61% inhibition
NEM
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0.1 mM, 90% inhibition
PCMB
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0.01 mM, 85% inhibition
Phenylmercuriacetate
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0.01 mM, no resiudal activity
S-adenosyl-L-homocysteine
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product inhibition
SKF 525
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0.5 mM, 56% inhibition
Zn2+
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0.1 mM, 45% resiudal activity
additional information
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not inhibitory: EDTA, Mg2+, Ca2+, iodoacetamide
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.034
4-hydroxy-3-methoxyacetophenone
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pH 8.0, 37°C
21.2
acetaminophen
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2
phenol
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0.0048 - 0.099
S-adenosyl-L-methionine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.041
S-adenosyl-L-homocysteine
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pH 8.0, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
101
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pH 8.0, 37°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.6 - 8.3
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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low activity
Manually annotated by BRENDA team
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low activity
Manually annotated by BRENDA team
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low activity
Manually annotated by BRENDA team
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low activity
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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from erythrocyte
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 54000, SDS-PAGE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
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rapid inactivation above
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-4°C, 100 mM potassium phosphate buffer, pH 6.5, 1 mM dithiothreitol, 75% loss of activity, in presence of 10% glycerol 5% loss of activtiy
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2°C, 100 mM potassium phosphate buffer, pH 6.5, 1 mM dithiothreitol, a half-life of approximately 30 h
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE