Information on EC 2.1.1.46 - isoflavone 4'-O-methyltransferase

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The expected taxonomic range for this enzyme is: Cicer arietinum

EC NUMBER
COMMENTARY hide
2.1.1.46
-
RECOMMENDED NAME
GeneOntology No.
isoflavone 4'-O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + a 4'-hydroxyisoflavone = S-adenosyl-L-homocysteine + a 4'-methoxyisoflavone
show the reaction diagram
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-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
formononetin biosynthesis
-
-
isoflavonoid biosynthesis II
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-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:4'-hydroxyisoflavone 4'-O-methyltransferase
Requires Mg2+ for activity. The enzyme catalyses the methylation of daidzein and genistein. It does not methylate naringenin, apigenin, luteolin or kaempferol.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
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 + 5,7,4'trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,7-dihydroxy-4'-O-methylisoflavone
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 7 hydroxy-4'-methoxylisoflavone
show the reaction diagram
-
i.e. daidzein. The reaction follows an ordered BiBi mechanism with S-adenosylmethionine and S-adenosylhomocysteine as leading reaction partners
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 7-hydroxy-4'-O-methylisoflavone
show the reaction diagram
additional information
?
-
-
no methylation of: p-hydroxycinnamic acid, p-hydroxybenzoic acid, 3,4-dihydroxycinnamic acid, naringenin, (5,7,4'-trihydroxyflavanone), apigenin (5,7,4'-trihydroxyflavone), luteolin (5,7,3',4'-tetrahydroxyflavone), kaempferol (3,5,7,4'-tetrahydroxyflavone), wedelolactone (5,3',4'-trihydroxy-7-methoxycoumestone)
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-
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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 + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 7-hydroxy-4'-O-methylisoflavone
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
does not require Mg2+ or other divalent cations
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-chloromercuribenzoate
-
0.001 50% inhibition
Ba2+
-
1 mM, 25% inhibition
Cd2+
-
1 mM, complete inhibition
Cu2+
-
1 mM, complete inhibition
Fe2+
-
1 mM, 78% inhibition
Mn2+
-
1 mM, 43% inhibition
S-adenosyl-L-homocysteine
-
-
Zn2+
-
1 mM, complete inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.08
7,4'-dihydroxyisoflavone
-
pH 8.8, 30C
0.16
S-adenosyl-L-methionine
-
pH 8.8, 30C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.03 - 0.3
S-adenosyl-L-homocysteine
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.6
-
in Tris-HCl buffer
9
-
in glycine-NaOH buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 10
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pH 7.5: about 40% of maximal activity (Tris-HCl buffer), pH 10.0: about 25% of maximal activity (glycine-NaOH buffer)
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
110000
-
gel filtration
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE