Information on EC 1.1.1.334 - methylecgonone reductase

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The expected taxonomic range for this enzyme is: Erythroxylum coca

EC NUMBER
COMMENTARY hide
1.1.1.334
-
RECOMMENDED NAME
GeneOntology No.
methylecgonone reductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ecgonine methyl ester + NADP+ = ecgonone methyl ester + NADPH + H+
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
cocaine biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
ecgonine methyl ester:NADP+ oxidoreductase
The enzyme from the plant Erythroxylum coca catalyses the penultimate step in the biosynthesis of cocaine. In vivo the reaction proceeds in the opposite direction. With NADH instead of NADPH the reaction rate is reduced to 14%. The enzyme also reduces tropinone, nortropinone and 6-hydroxytropinone but with lower reaction rates.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
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
6-hydroxytropinone + NADPH + H+
? + NADP+
show the reaction diagram
reduction at 45% of the activity with methylecgonone
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-
r
methyl ecgonone + NADH + H+
methyl ecgonine + NAD+
show the reaction diagram
NADH can substitute for NADPH with 14% of the activity compared to NADPH
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-
r
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
show the reaction diagram
nortropinone + NADPH + H+
? + NADP+
show the reaction diagram
reduction at 6% of the activity with methylecgonone
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-
r
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
reduction at 36% of the activity with methylecgonone
-
-
r
additional information
?
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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
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
show the reaction diagram
E7C196
cocaine biosynthesis
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-
r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
14% of the activity with NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Co2+
5 mM, inhibition by less than 30%
Cu2+
5 mM, 8% residual activity
Fe2+
5 mM, inhibition by less than 30%
methyl ecgonine
-
methyl ecgonone
-
Zn2+
5 mM, 58% residual activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.151
methyl ecgonine
pH 6.8, temperature not specified in the publication
0.069
methyl ecgonone
pH 6.8, temperature not specified in the publication
0.0009
NADP+
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002673
methyl ecgonine
substrate inhibition, pH 6.8, temperature not specified in the publication
0.001136
methyl ecgonone
substrate inhibition, pH 6.8, temperature not specified in the publication
0.506
NADP+
substrate inhibition, pH 6.8, temperature not specified in the publication
0.00248
NADPH
substrate inhibition, pH 6.8, temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0002669
pH 6.8 temperature not specified in the publication
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8
reduction of methyl ecgonone
9.8
oxidation of methyl ecgonine
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
less than 20% of activity compared to young leaves
Manually annotated by BRENDA team
highest activity in young leaves
Manually annotated by BRENDA team
of young leaves
Manually annotated by BRENDA team
less than 20% of activity compared to young leaves
Manually annotated by BRENDA team
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
36910
calculated from the amino acid sequence
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
30 min, more than 30% loss of activity
37
30 min, more than 70% loss of activity
50
30 min, complete inactivation abvoe 50°C
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli