Information on EC 2.1.1.146 - (iso)eugenol O-methyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.1.1.146
-
RECOMMENDED NAME
GeneOntology No.
(iso)eugenol O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + isoeugenol = S-adenosyl-L-homocysteine + isomethyleugenol
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
volatile cinnamoic ester biosynthesis
-
-
Phenylpropanoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:isoeugenol O-methyltransferase
Acts on eugenol and chavicol as well as isoeugenol.
CAS REGISTRY NUMBER
COMMENTARY hide
191744-33-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
synonym Ocimum sanctum
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
var. spontanea
-
-
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-methoxy-4-methylphenol
S-adenosyl-L-homocysteine + 1,2-dimethoxy-4-methylbenzene
show the reaction diagram
-
16.8% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + 2-methoxyphenol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
4% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + 5-methoxyeugenol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
about 18% of the activity with isoeugenol
-
-
?
S-adenosyl-L-methionine + chavicol
S-adenosyl-L-homocysteine + estragol
show the reaction diagram
24% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + dihydrochavicol
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
about 23% of the activity with isoeugenol
-
-
?
S-adenosyl-L-methionine + dihydroeugenol
S-adenosyl-L-homocysteine + methyldihydroeugenol
show the reaction diagram
-
about 50% of the activity with isoeugenol
-
-
?
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
show the reaction diagram
S-adenosyl-L-methionine + guaiacol
S-adenosyl-L-homocysteine + 1,2-dimethoxybenzene
show the reaction diagram
29.9% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
show the reaction diagram
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + methylisoeugenol
show the reaction diagram
S-adenosyl-L-methionine + t-anol
S-adenosyl-L-homocysteine + t-anethole
show the reaction diagram
-
methylation of the p-OH group. 45% of the rate with isoeugenol
-
-
?
S-adenosyl-L-methionine + trans-isoeugenol
S-adenosyl-L-homocysteine + (E)-2',3'-dimethoxy-1-propenylbenzene
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + zingerone
S-adenosyl-L-homocysteine + 4-(3,4-dimethoxyphenyl)-butan-2-one
show the reaction diagram
-
26.8% of the activity with eugenol
-
-
?
additional information
?
-
-
no substrate: chavicol, eugenol, guaiacol, caffeic acid, 2-propylphenol
-
-
-
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 + eugenol
S-adenosyl-L-homocysteine + methyleugenol
show the reaction diagram
-
the enzyme is involved in the production of the floral volatile compounds methyleugenol and methylisoeugenol
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
show the reaction diagram
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + methylisoeugenol
show the reaction diagram
-
the enzyme is involved in the production of the floral volatile compounds methyleugenol and methylisoeugenol
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
methylation of eugenol and isoeugenol
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ca2+
-
5 mM, weak inhibition
Fe3+
-
5 mM, strong inhibition
K+
-
5 mM, weak inhibition
Mg2+
-
5 mM, 33% inhibition
Na+
-
5 mM, weak inhibition
NH4+
-
5 mM, weak inhibition
additional information
-
not inhibitory: 2.5 mM K+, Na+, Ca2+, and Mg2+
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.007
chavicol
-
0.003 - 0.159
Eugenol
0.0193 - 0.214
Isoeugenol
0.005 - 0.0545
S-adenosyl-L-methionine
0.01
trans-isoeugenol
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00087
chavicol
Ocimum basilicum
Q93WU2
-
0.0031 - 0.019
Eugenol
0.015 - 0.031
Isoeugenol
0.0013
t-isoeugenol
Ocimum basilicum
Q93WU2
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.78
Isoeugenol
Pimpinella anisum
-
pH 7.5, 25C
3640
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
methylation of eugenol and isoeugenol
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.4
calculated from amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
expression throughout the plant with highest level in developing fruit
Manually annotated by BRENDA team
additional information
-
expression throughout the plant with highest level in developing fruit
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
81000
gel filtration
88000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 22490, calculated from amino acid sequence
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
-
stable for at least 30 min
35
-
30 min, stable up to
37
-
stable for at least 30 min
45
-
30 min, activity is dramatically decreased
50
-
30 min, 88% residual activity
65
-
30 min, less than 5% residual activity
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme exhibits enhanced expression in juvenile stage that increases further during preflowering but decreases at flowering and further at postflowering