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EC Tree
IUBMB Comments 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.
The enzyme appears in viruses and cellular organisms
Synonyms
MecgoR,
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ecgonine methyl ester + NADP+ = ecgonone methyl ester + NADPH + H+
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-
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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.
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6-hydroxytropinone + NADPH + H+
? + NADP+
reduction at 45% of the activity with methylecgonone
-
-
r
methyl ecgonone + NADH + H+
methyl ecgonine + NAD+
NADH can substitute for NADPH with 14% of the activity compared to NADPH
-
-
r
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
nortropinone + NADPH + H+
? + NADP+
reduction at 6% of the activity with methylecgonone
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
reduction at 36% of the activity with methylecgonone
-
-
r
additional information
?
-
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
-
-
-
r
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
cocaine biosynthesis
-
-
r
additional information
?
-
no reduction of 8-thiabicyclo[3.2.1]octan-3-one, cyclohexanone, cyclooctanone, N-methyl-4-piperidone
-
-
?
additional information
?
-
-
no reduction of 8-thiabicyclo[3.2.1]octan-3-one, cyclohexanone, cyclooctanone, N-methyl-4-piperidone
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-
?
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methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
cocaine biosynthesis
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-
r
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NADH
14% of the activity with NADPH
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additional information
not activated by monovalent or divalent cations
additional information
-
not activated by monovalent or divalent cations
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Co2+
5 mM, inhibition by less than 30%
Cu2+
5 mM, 8% residual activity
Fe2+
5 mM, inhibition by less than 30%
Zn2+
5 mM, 58% residual activity
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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+
pH 6.8, temperature not specified in the publication
0.0009
NADPH
pH 6.8, temperature not specified in the publication
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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
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0.0002669
pH 6.8 temperature not specified in the publication
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6.8
reduction of methyl ecgonone
9.8
oxidation of methyl ecgonine
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UniProt
brenda
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less than 20% of activity compared to young leaves
brenda
highest activity in young leaves
brenda
of young leaves
brenda
-
brenda
less than 20% of activity compared to young leaves
brenda
additional information
no activity in mature leaves or in roots
brenda
additional information
-
no activity in mature leaves or in roots
brenda
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MER_ERYCB
327
0
36908
Swiss-Prot
other Location (Reliability: 3 )
A0A396HKH1_MEDTR
Medicago tribuloides
104
0
12356
TrEMBL
other Location (Reliability: 5 )
A0A396HKH1_MEDTR
104
0
12356
TrEMBL
other Location (Reliability: 5 )
A0A396HGB9_MEDTR
322
0
36070
TrEMBL
other Location (Reliability: 2 )
A0A2P6P1M4_ROSCH
329
0
36540
TrEMBL
other Location (Reliability: 3 )
A0A396HGC2_MEDTR
317
0
35465
TrEMBL
other Location (Reliability: 2 )
A0A396I729_MEDTR
184
0
21094
TrEMBL
other Location (Reliability: 1 )
A0A2G9IBC0_9LAMI
329
0
36731
TrEMBL
other Location (Reliability: 3 )
A0A396ICF3_MEDTR
111
0
12285
TrEMBL
other Location (Reliability: 2 )
A0A2G9HML7_9LAMI
318
0
35824
TrEMBL
other Location (Reliability: 3 )
A0A396HIG8_MEDTR
303
0
34398
TrEMBL
other Location (Reliability: 2 )
A0A396I9I4_MEDTR
108
0
11796
TrEMBL
other Location (Reliability: 3 )
A0A2G9HMJ1_9LAMI
318
0
35815
TrEMBL
other Location (Reliability: 3 )
A0A2G9I7B5_9LAMI
329
0
36733
TrEMBL
other Location (Reliability: 3 )
A0A396I713_MEDTR
172
0
19775
TrEMBL
other Location (Reliability: 5 )
A0A2G9G9J4_9LAMI
279
0
31015
TrEMBL
other Location (Reliability: 5 )
A0A396IAX1_MEDTR
172
0
19710
TrEMBL
other Location (Reliability: 4 )
A0A2G9FYJ2_9LAMI
316
0
35480
TrEMBL
other Location (Reliability: 5 )
A0A396I701_MEDTR
102
0
11186
TrEMBL
other Location (Reliability: 2 )
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36910
calculated from the amino acid sequence
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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
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expressed in Escherichia coli
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Jirschitzka, J.; Schmidt, G.W.; Reichelt, M.; Schneider, B.; Gershenzon, J.; D'Auria, J.C.
Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae
Proc. Natl. Acad. Sci. USA
109
10304-10309
2012
Erythroxylum coca (E7C196), Erythroxylum coca
brenda
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1.1.1.334 methylecgonone reductase
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