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Information on EC 2.1.1.6 - catechol O-methyltransferase and Organism(s) Homo sapiens and UniProt Accession P21964

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EC Tree
     2 Transferases
         2.1 Transferring one-carbon groups
             2.1.1 Methyltransferases
                2.1.1.6 catechol O-methyltransferase
IUBMB Comments
The mammalian enzyme acts more rapidly on catecholamines such as adrenaline or noradrenaline than on catechols.
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Select one or more organisms in this record:
This record set is specific for:
Homo sapiens
UNIPROT: P21964
Word Map
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
The taxonomic range for the selected organisms is: Homo sapiens
Synonyms
catechol-o-methyltransferase, catechol-o-methyl transferase, s-comt, mb-comt, comt i, comt1, comt ii, catechol methyltransferase, ctomt1, comt2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
catechol methyltransferase
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catechol-O-methyl transferase
247
-
catechol-O-methyltransferase
247
-
catechol-O-transferase
247
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catecholamine O-methyltransferase
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COMT I
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COMT II
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-
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-
COMT1
247
isoform
COMT2
247
isoform
MB-COMT
methyltransferase, catechol
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-
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S-COMT
SCOMT
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + a catechol = S-adenosyl-L-homocysteine + a guaiacol
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
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O-methylation
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:catechol O-methyltransferase
The mammalian enzyme acts more rapidly on catecholamines such as adrenaline or noradrenaline than on catechols.
CAS REGISTRY NUMBER
COMMENTARY hide
9012-25-3
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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 + 1-hydroxyestradiol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 2,3-dihydroxybenzaldehyde
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 2,3-dihydroxynaphthalene
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 2-(1-thienyl)ethyl-3,4-dihydroxybenzylcyano acetate
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 3,4-dihydroxyacetophenone
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 3,4-dihydroxybenzoic acid ethyl ester
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 3,4-dihydroxymandelic acid
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 3,4-dihydroxyphenylacetic acid
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 3,4-dihydroxyphenylglycol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 3-fluorocatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 3-methoxy-5-bromocatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 3-methoxycatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 4-chlorocatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
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?
S-adenosyl-L-methionine + 4-hydroxyestradiol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
?
S-adenosyl-L-methionine + 4-isopropylcatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 4-methylcatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 4-nitrocatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
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?
S-adenosyl-L-methionine + 4-tert-butyl-5-methoxycatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
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?
S-adenosyl-L-methionine + 4-tert-butylcatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 5-hydroxydopamine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 6-hydroxydopa
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 6-hydroxydopamine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + adrenaline
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
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?
S-adenosyl-L-methionine + carbidopa
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + catechin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + catechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
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?
S-adenosyl-L-methionine + chlorogenic acid
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
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?
S-adenosyl-L-methionine + dihydrexidine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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?
S-adenosyl-L-methionine + dobutamine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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-
-
?
S-adenosyl-L-methionine + dopamine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
S-adenosyl-L-methionine + epicatechin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
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?
S-adenosyl-L-methionine + epicatechin gallate
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
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?
S-adenosyl-L-methionine + epigallocatechin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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-
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?
S-adenosyl-L-methionine + epigallocatechin gallate
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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-
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?
S-adenosyl-L-methionine + ethyl-3,4-dihydroxybenzylcyanoacetate
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
S-adenosyl-L-methionine + gallic acid
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
S-adenosyl-L-methionine + L-Dopa
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
?
S-adenosyl-L-methionine + methyl gallate
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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?
S-adenosyl-L-methionine + noradrenaline
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
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?
S-adenosyl-L-methionine + pyrogallol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
S-adenosyl-L-methionine + rosmarinic acid
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
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?
S-adenosyl-L-methionine + salsoline
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
S-adenosyl-L-methionine + salsoline-1-carboxylic acid
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
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?
S-adenosyl-L-methionine + SKF38393
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
S-adenosyl-L-methionine + tetrachlorocatechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
(+)-catechin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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3'-O-methyl derivatives are consistently the main metabolites, 3'-O-methyl derivatives are consistently the main metabolites, meta/para ratio of the metabolites is approximately 25:1
-
?
(+)-epicatechin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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?
(-)-epicatechin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
(-)-epigallocatechin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
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?
(-)-epigallocatechin-3-O-gallate + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
(R)-1,2-dihydroxy-4-[2-(methylamino)butyl]benzene + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
(R)-3,4-dihydroxymethamphetamine + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
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?
(R)-N-ethyl-3,4-dihydroxyamphetamine + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
(S)-1,2-dihydroxy-4-[2-(methylamino)butyl]benzene + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
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?
(S)-3,4-dihydroxymethamphetamine + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
(S)-N-ethyl-3,4-dihydroxyamphetamine + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
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?
2-hydroxyestradiol + S-adenosyl-L-methionine
2-hydroxyestradiol 3-methyl ether + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
2-hydroxyestradiol + S-adenosyl-L-methionine
2-methoxyestradiol + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
2-hydroxyestradiol + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + 2-methoxyestradiol + 2-hydroxy-3-methoxyestradiol
show the reaction diagram
-
-
-
-
?
2-hydroxyestradiol + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
2-hydroxyestradiol-17beta + S-adenosyl-L-methionine
2-methoxyestradiol-17beta + 2-hydroxyestradiol-17beta methyl ether + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
?
3,4-dihydroxybenzoic acid + S-adenosyl-L-methionine
4-hydroxy-3-methoxybenzoic acid + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
the meta/para ratio of the metabolites is approximately 4.5
-
?
3,4-dihydroxybenzoic acid + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
3,5-dinitrocatechol + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
3-hydroxytyramine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + 3-methoxytyramine
show the reaction diagram
-
-
-
-
?
4-hydroxyestradiol + S-adenosyl-L-methionine
(17beta)-estra-1(10),2,4-triene-3,4,17-triol + S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
MCF-10F cells oxidize 4-hydroxyestradiol to estrone (estradiol)-3,4-quinones, which react with DNA to form the depurinating N3Ade and N7Gua adducts
-
-
?
4-hydroxyestradiol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
4-hydroxyestradiol + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
dobutamine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
dopa + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
dopamine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + 3-O-methyldopamine
show the reaction diagram
-
-
-
-
?
dopamine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
epinephrine + S-adenosyl-L-methionine
metanephrine + S-adenosyl-L-homocysteine
show the reaction diagram
esculetin + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
isoetharine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
isoproterenol + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
L-dopa + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + 3-O-methyl-L-dopa
show the reaction diagram
-
-
-
-
?
noradrenaline + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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-
-
-
?
norepinephrine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + normetanephrine
show the reaction diagram
-
-
-
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?
procyanidin dimer B1 + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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flavanyl units of procyanidins are methylated consecutively, leading to monomethylated and dimethylated dimeric metabolites
-
?
procyanidin dimer B2 + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
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flavanyl units of procyanidins are methylated consecutively, leading to monomethylated and dimethylated dimeric metabolites
-
?
procyanidin dimer B3 + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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flavanyl units of procyanidins are methylated consecutively, leading to monomethylated and dimethylated dimeric metabolites
-
?
procyanidin dimer B4 + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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flavanyl units of procyanidins are methylated consecutively, leading to monomethylated and dimethylated dimeric metabolites
-
?
procyanidin dimer B5 + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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flavanyl units of procyanidins are methylated consecutively, leading to monomethylated and dimethylated dimeric metabolites
-
?
procyanidin dimer B7 + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
flavanyl units of procyanidins are methylated consecutively, leading to monomethylated and dimethylated dimeric metabolites
-
?
procyanidin trimer C1 + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
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flavanyl units of procyanidins are methylated consecutively, leading to monomethylated, dimethylated, and trimethylated C1 metabolites
-
?
S-adenosyl-L-homocysteine + 4''-O-methyl epigallocatechin gallate
S-adenosyl-L-homocysteine + 4',4''-di-O-methyl epigallocatechin gallate
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 2-hydroxyestradiol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 3,4-dihydroxy-L-Phe
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxyequilenin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxyestradiol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + a catechol
?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + catechin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + catechol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + dopamine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + epicatechin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + epigallocatechin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + epigallocatechin gallate
S-adenosyl-L-homocysteine + 4''-O-methyl epigallocatechin gallate
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + epigallocatechin-3-gallate
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + esculetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + fisetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + L-Dopa
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + levodopa
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + norepinephrine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
S-adenosyl-L-methionine + scopoletin
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
-
?
tolcapone + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
inhibitor of isoform MB-COMT, substrate of isoform S-COMT
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-
-
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
4-hydroxyestradiol + S-adenosyl-L-methionine
(17beta)-estra-1(10),2,4-triene-3,4,17-triol + S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
MCF-10F cells oxidize 4-hydroxyestradiol to estrone (estradiol)-3,4-quinones, which react with DNA to form the depurinating N3Ade and N7Gua adducts
-
-
?
4-hydroxyestradiol + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
in the mammary gland, catechol estrogens are predominately inactivated by catechol-O-methyltransferase. in the isoflavone-induced. The estrogen receptor is involved in the down-regulation of COMT expression
-
-
?
S-adenosyl-L-methionine + a catechol
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
-
may partly substitute for Mg2+
Mg2+
-
Mg(II) bound to COMT is the most potent of the studied cations
additional information
-
activity of the enzyme is strongly influenced by the nature of the buffer
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ca2+
-
quantum mechanical/molecular mechanical dynamics study
Fe3+
-
quantum mechanical/molecular mechanical dynamics study
(-)-epicatechin-3-gallate
-
IC50: 0.0002 mM with 2-hydroxyestradiol as substrate, IC50: 0.0003 mM with 4-hydroxyestradiol as substrate
(-)-epigallocatechin
-
IC50: 0.044 mM with 2-hydroxyestradiol as substrate, IC50: 0.05 nM with 4-hydroxyestradiol as substrate
(-)-epigallocatechin-3-gallate
(-)-epigallocatechin-3-gallate-3''-O-glucuronide
-
IC50: 0.002 mM with 2-hydroxyestradiol as substrate, IC50: 0.0025 mM with 4-hydroxyestradiol as substrate
(-)-epigallocatechin-3-gallate-3'-O-glucuronide
-
IC50: 0.0018 mM with 2-hydroxyestradiol as substrate, IC50: 0.0023 mM with 4-hydroxyestradiol as substrate
(-)-epigallocatechin-3-gallate-4''-O-glucuronide
-
IC50: 0.0025 mM with 2-hydroxyestradiol as substrate, IC50: 0.004 mM with 4-hydroxyestradiol as substrate
(-)-epigallocatechin-3-gallate-7-O-glucuronide
-
IC50: 600 nM with 2-hydroxyestradiol as substrate, IC50: 800 nM with 4-hydroxyestradiol as substrate
(-)-epigallocatechin-3-O-gallate
(-)epicatechin
-
IC50: 0.06 mM with 2-hydroxyestradiol as substrate, IC50: 0.08 mM with 4-hydroxyestradiol as substrate
(2-amino-3-methylbutanoyloxy)methyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
(2R,3R)-5,7-bis(acetyloxy)-2-[3,4,5-tris(acetyloxy)phenyl]-3,4-dihydro-2H-chromen-3-yl 3,4-bis(acetyloxy)-5-(2-oxopropyl)benzoate
-
-
(2R,3S)-1,2,3,4-tetrahydronaphthalene-2,3-diyl bis(3,4,5-trihydroxybenzoate)
-
-
(2R,3S)-1,2,3,4-tetrahydronaphthalene-2,3-diyl bis(3,5-dihydroxybenzoate)
-
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(2R,3S)-1,2,3,4-tetrahydronaphthalene-2,3-diyl bis[3,4,5-tris(acetyloxy)benzoate]
-
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(2R,3S)-1,2,3,4-tetrahydronaphthalene-2,3-diyl bis[3,5-bis(acetyloxy)benzoate]
-
-
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
1,2-dihydroxy-4-[2-(methylamino)butyl]benzene
-
uncompetitive inhibitor of the sCOMT isoform
1-(butyryloxy)ethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
1-(isobutyryloxy)ethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
1-[1-(2-chlorobenzyl)-1H-benzimidazol-4-yl]-3-hydroxypyridin-4(1H)-one
-
-
1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-5-hydroxy-2-(1-hydroxyethyl)pyridin-4(1H)-one
-
-
2-Hydroxyestradiol-17beta 3-methyl ether
-
product inhibition
2-hydroxyoestrogen
-
-
2-methoxyestradiol-17beta
-
product inhibition
3,4-dihydroxymethamphetamine
-
uncompetitive inhibitor of the sCOMT isoform
3-chloro-5,6-dihydroxy-7-nitro-1-benzothiophene-2-carboxylic acid
-
-
4'-4''-di-O-methyl-epigallocatechin-3-gallate
-
IC50: 0.00015 mM with 2-hydroxyestradiol or 4-hydroxyestradiol as substrate, competitive with respect S-adenyosylmethionine, noncompetitive with respect to catechol
4'-O-methyl-(-)-epigallocatechin
-
IC50: 0.032 mM with 2-hydroxyestradiol as substrate, IC50: 0.04 mM with 4-hydroxyestradiol as substrate
4'-O-methyl-epigallocatechin-3-gallate
-
IC50: 0.0001 mM with 2-hydroxyestradiol or 4-hydroxyestradiol as substrate
4-(tert-octyl)phenol
-
causes significant inhibition of enzyme activity
4-hydroxyequilenin
-
inhibits its own methylation by COMT at higher concentrations in the presence of the reducing agent dithiothreitol, irreversible inhibitor, the inhibitor causes formation of intermolecular disulfide bonds, cys33 in recombinant human soluble COMT is the residue most likely modified by the inhibitor
5-hydroxy-1-[3-(isoquinolin-4-yl)phenyl]-2-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one
-
-
ascorbic acid
-
-
benzyl butyl phthalate
-
causes significant inhibition of enzyme activity
benzyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
butyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
butyryloxymethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
Ca2+
-
-
caffeic acid
caffeic acid phenethyl ester
-
COMT from liver, using 2-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from liver, using 4-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C
catechin
CGP 28014
-
-
chlorogenic acid
-
COMT from liver, using 2-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from liver, using 4-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from placenta, using 2-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from placenta, using 4-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C
chrysin
-
slight inhibition at 0.3 mM
daidzein
-
soy isoflavones at hormonally active concentrations cause a significant reduction of both COMT mRNA levels and COMT activity as well as of the methylation of 4-hydroxyestradiol
dibutyl phthalate
-
causes significant inhibition of enzyme activity
dihydromyricetin
-
competitive
diisononyl phthalate
-
causes significant inhibition of enzyme activity
dioctyl phthalate
-
causes significant inhibition of enzyme activity
dobutamine
-
competitive to dopamine
dopamine
-
competitive to dobutamine
entacapone
-
-
epicatechin
epigallocatechin
-
-
epigallocatechin-3-gallate
-
inhibition in vitro. Supplementation with a high dose does not impair the activity of COMT
fisetin
flavone
-
IC50: 0.00549 mM
gallic acid
-
-
genistein
iodoacetic acid
-
-
isobutyryloxymethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
isopropyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
methyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
Mg2+
-
required for activity
myricetin
-
competitive
Myricitrin
-
competitive
N-(2-[2-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-ethoxy]-ethyl)-2,3-dihydroxy-5-nitro-benzamide
-
IC50: 0.002 mM
N-ethyl-3,4-dihydroxyamphetamine
-
uncompetitive inhibitor of the sCOMT isoform
N-[(E)-4-[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-but-2-enyl]-2,3-dihydroxy-5-nitro-benzamide
-
IC50: 9 nM
N-[2-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]ethyl]-2,3-dihydroxy-5-nitrobenzene-1-carboxamide
-
IC50: 60 nM
N-[3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]propyl]2,3-dihydroxy-5-nitrobenzene-1-carboxamide
-
IC50: 200 nM
N-[4-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]butyl]-2,3-dihydroxy-5-nitrobenzene-1-carboxamide
-
IC50: 0.005 mM
N-[[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl]-2,3-dihydroxy-5-nitrobenzene-1-carboxamide
-
IC50: 0.09 mM, very potent bisubstrate inhibitor
nebicapone
-
-
nitecapone
-
-
nordihydroguaiaretic acid
-
-
propyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
-
purpurogallin
-
decreased Vmax and increased Km-value
purpurogallin carboxylic acid
-
-
pyrogallol
-
-
quercetin
Ro 41-0960
-
IC50: 5-42 nM
Ro41-0960
S-adenosyl-L-homocysteine
S-adenosyl-L-methionine
-
-
theaflavin-3,3'-digallate
-
decreased Vmax and increased Km-value
tolcapone
Triton X-100
-
-
tropolone
U-0521
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cysteine
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0022 - 0.0082
(-)-epicatechin
-
-
0.0039 - 0.0067
(-)-epigallocatechin
-
-
0.02
(R)-1,2-dihydroxy-4-[2-(methylamino)butyl]benzene
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.03
(R)-3,4-dihydroxymethamphetamine
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.09
(R)-N-ethyl-3,4-dihydroxyamphetamine
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.02
(S)-1,2-dihydroxy-4-[2-(methylamino)butyl]benzene
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.03
(S)-3,4-dihydroxymethamphetamine
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.07
(S)-N-ethyl-3,4-dihydroxyamphetamine
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.00032 - 0.0175
2-hydroxyestradiol
0.014
2-hydroxyestradiol-17beta
-
-
0.0024
4-hydroxyequilenin
-
pH 7.8
0.00037 - 0.0161
4-hydroxyestradiol
0.0022 - 0.0089
catechin
0.01 - 0.108
catechol
0.05
dobutamine
-
-
0.0033 - 0.44
dopamine
0.0043 - 0.0257
epicatechin
0.0117
epigallocatechin
-
-
0.004
epigallocatechin gallate
-
-
0.0288 - 0.3947
epinephrine
0.0015
fisetin
-
S-COMT, 0.25 mM S-adenosyl-L-methionine
0.266 - 0.613
levodopa
0.024 - 0.369
norepinephrine
0.0015
quercetin
-
S-COMT, 0.25 mM S-adenosyl-L-methionine
0.0031 - 0.1453
S-adenosyl-L-methionine
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.085 - 0.99
2-hydroxyestradiol
0.1
4-hydroxyequilenin
-
pH 7.8
0.035 - 0.077
4-hydroxyestradiol
0.18 - 0.26
catechin
0.088 - 0.19
dopamine
0.17 - 0.315
epicatechin
0.085 - 0.25
epinephrine
0.04 - 0.18
norepinephrine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00032 - 0.00037
(-)-epigallocatechin-3-gallate
0.000006
(2-amino-3-methylbutanoyloxy)methyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0000016
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0000166
1-(butyryloxy)ethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.000017
1-(isobutyryloxy)ethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.000001
3-chloro-5,6-dihydroxy-7-nitro-1-benzothiophene-2-carboxylic acid
-
Ki value below 0.000001 mM, pH not specified in the publication, temperature not specified in the publication
0.026
4-hydroxyequilenin
-
pH 7.8, inhibition og methylation of 4-hydroxyestradiol
0.0000102
benzyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0000013
butyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0000106
butyryloxymethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0009
dihydromyricetin
-
37°C, pH not specified in the publication
0.0003
entacapone
-
-
0.000017
isobutyryloxymethyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0000011
isopropyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0000022
methyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.0002
myricetin
-
37°C, pH not specified in the publication
0.0005
Myricitrin
-
37°C, pH not specified in the publication
0.00102
nitecapone
-
-
0.0000092
propyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
-
pH not specified in the publication, temperature not specified in the publication
0.001 - 0.039
S-adenosyl-L-homocysteine
0.00027
tolcapone
-
-
0.005
tropolone
-
plus dopamine
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0003
(-)-epicatechin-3-gallate
Homo sapiens
-
IC50: 0.0002 mM with 2-hydroxyestradiol as substrate, IC50: 0.0003 mM with 4-hydroxyestradiol as substrate
0.044 - 0.05
(-)-epigallocatechin
0.00007 - 0.00008
(-)-epigallocatechin-3-gallate
0.0025
(-)-epigallocatechin-3-gallate-3''-O-glucuronide
Homo sapiens
-
IC50: 0.002 mM with 2-hydroxyestradiol as substrate, IC50: 0.0025 mM with 4-hydroxyestradiol as substrate
0.0023
(-)-epigallocatechin-3-gallate-3'-O-glucuronide
Homo sapiens
-
IC50: 0.0018 mM with 2-hydroxyestradiol as substrate, IC50: 0.0023 mM with 4-hydroxyestradiol as substrate
0.004
(-)-epigallocatechin-3-gallate-4''-O-glucuronide
Homo sapiens
-
IC50: 0.0025 mM with 2-hydroxyestradiol as substrate, IC50: 0.004 mM with 4-hydroxyestradiol as substrate
0.0006 - 0.0008
(-)-epigallocatechin-3-gallate-7-O-glucuronide
0.00004 - 0.00054
(-)-epigallocatechin-3-O-gallate
0.08
(-)epicatechin
Homo sapiens
-
IC50: 0.06 mM with 2-hydroxyestradiol as substrate, IC50: 0.08 mM with 4-hydroxyestradiol as substrate
0.029
(2R,3S)-1,2,3,4-tetrahydronaphthalene-2,3-diyl bis(3,5-dihydroxybenzoate)
Homo sapiens
-
70-79% inhibition at 0.025-0.05 mM
0.3
1,2-dihydroxy-4-[2-(methylamino)butyl]benzene
Homo sapiens
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.0000449 - 0.000857
1-[1-(2-chlorobenzyl)-1H-benzimidazol-4-yl]-3-hydroxypyridin-4(1H)-one
0.000039 - 0.000226
1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-5-hydroxy-2-(1-hydroxyethyl)pyridin-4(1H)-one
0.2
3,4-dihydroxymethamphetamine
Homo sapiens
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.00015
4'-4''-di-O-methyl-epigallocatechin-3-gallate
Homo sapiens
-
IC50: 0.00015 mM with 2-hydroxyestradiol or 4-hydroxyestradiol as substrate, competitive with respect S-adenyosylmethionine, noncompetitive with respect to catechol
0.04
4'-O-methyl-(-)-epigallocatechin
Homo sapiens
-
IC50: 0.032 mM with 2-hydroxyestradiol as substrate, IC50: 0.04 mM with 4-hydroxyestradiol as substrate
0.0001
4'-O-methyl-epigallocatechin-3-gallate
Homo sapiens
-
IC50: 0.0001 mM with 2-hydroxyestradiol or 4-hydroxyestradiol as substrate
0.000063 - 0.000175
5-hydroxy-1-[3-(isoquinolin-4-yl)phenyl]-2-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one
0.00164 - 0.0153
catechin
0.00196 - 0.0532
epicatechin
0.006 - 0.015
epigallocatechin
0.0021 - 0.0045
fisetin
0.00549
flavone
Homo sapiens
-
IC50: 0.00549 mM
0.002
N-(2-[2-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-ethoxy]-ethyl)-2,3-dihydroxy-5-nitro-benzamide
Homo sapiens
-
IC50: 0.002 mM
0.1
N-ethyl-3,4-dihydroxyamphetamine
Homo sapiens
-
isoform sCOMT, in phosphate buffer (pH 7.4)
0.000009
N-[(E)-4-[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-but-2-enyl]-2,3-dihydroxy-5-nitro-benzamide
Homo sapiens
-
IC50: 9 nM
0.00006
N-[2-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]ethyl]-2,3-dihydroxy-5-nitrobenzene-1-carboxamide
Homo sapiens
-
IC50: 60 nM
0.0002
N-[3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]propyl]2,3-dihydroxy-5-nitrobenzene-1-carboxamide
Homo sapiens
-
IC50: 200 nM
0.005
N-[4-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]butyl]-2,3-dihydroxy-5-nitrobenzene-1-carboxamide
Homo sapiens
-
IC50: 0.005 mM
0.09
N-[[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl]-2,3-dihydroxy-5-nitrobenzene-1-carboxamide
Homo sapiens
-
IC50: 0.09 mM, very potent bisubstrate inhibitor
0.00048 - 0.0085
quercetin
0.000005 - 0.000042
Ro 41-0960
Homo sapiens
-
IC50: 5-42 nM
0.0000067
tolcapone
Homo sapiens
-
isoform MB-COMT, pH 7.4, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.092
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8 - 8.4
-
leads to maximal formation of 2-methoxyestradiol-17beta
7 - 8
-
methylation of 2-hydroxyestradiol or 4-hydroxyestradiol by MB-COMT; methylation of 2-hydroxyestradiol or 4-hydroxyestradiol by S-COMT
9.2
-
leads to maximal formation of 2- and 3-monomethyl ether
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
assay at
42
-
2-hydroxyestradiol-17beta
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
mononuclear cell
Manually annotated by BRENDA team
-
COMT2 is highly expressed in sensory hair cells of the inner ear
Manually annotated by BRENDA team
-
leukocyte exposure to morphine down-regulates catechol-O-methyl transferase and CYP2D6 by approximately 50% compared with control values. Exposure of white blood cells to 0.001 mM S-nitroso-N-acetyl-DL-penicillamine, a nitric oxide donor, reduces the expression of CYP2D6 and COMT. Prior naloxone (0.001 mM) or N-nitro-L-arginine methyl ester (0.1 mM) addition abrogates down-regulating activity of morphine, demonstrating morphine is initiating its actions via stimulating constitutive NO synthase derived NO release via the mu3 opiate receptor splice variant
Manually annotated by BRENDA team
-
no effect of sex on COMT activity
Manually annotated by BRENDA team
-
healthy
Manually annotated by BRENDA team
-
Val158Met polymorphism within COMT and PvuII polymorphism within ESR1, alone or together with physical activity may, at least partly, modulate muscle mass and performance phenotypes in older women. COMT Val158Met polymorphism is associated with muscle mass in that subjects with the LL genotype have significantly larger muscles than heterozygotes. Furthermore, within are observed than within other sedentary subjects or subjects with more active life-style
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
-
-
Manually annotated by BRENDA team
-
S-COMT, recombinant enzyme
Manually annotated by BRENDA team
-
MB-COMT, recombinant enzyme
Manually annotated by BRENDA team
-
S-COMT, recombinant enzyme
Manually annotated by BRENDA team
additional information