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Enzyme Nomenclature
Information on EC 1.14.13.71 - N-methylcoclaurine 3'-monooxygenase
Word Map on EC 1.14.13.71
- 1.14.13.71
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alkaloid
- poppy
- berberine
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s-n-methylcoclaurine
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benzylisoquinoline
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opium
- papaver
- codeinone
- somniferum
- sanguinarine
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s-reticuline
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elicitors
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narcotic
- jasmonate
- california
- eschscholzia
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benzophenanthridine
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p-450-dependent
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6-o-methyltransferase
- n-methyltransferase
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penultimate
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latex
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companion
- papaverine
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sieve
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coptis
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analgesics
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3'-hydroxylation
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jasmonate-induced
- japonica
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branch-point
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laticifers
- thebaine
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s-norcoclaurine
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morphinan
- biotechnology
- medicine
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.71
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RECOMMENDED NAME
GeneOntology No.
N-methylcoclaurine 3'-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-N-methylcoclaurine + NADPH + H+ + O2 = (S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydroxylation
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-
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(S)-N-methylcoclaurine, NADPH:oxygen oxidoreductase (3'-hydroxylating)
A heme-thiolate protein (P-450) involved in benzylisoquinoline alkaloid synthesis in higher plants.
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CAS REGISTRY NUMBER
COMMENTARY
202420-37-9
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
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enzyme silencing is associated with a 22% reduction in total alkaloid accumulation, with a notable decrease in the levels of thebaine and codeine compared with controls. In contrast, absolute levels of morphine and papaverine are not affected
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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-
-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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absolute requirement for an N-methyl group, a 4'-hydroxyl moiety and S-configuration at carbon atom 1
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?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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the enzyme is involved in the sanguinarine biosynthetic pathway, overview
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-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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-
-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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the enzyme catalyzes a key regulation step in morphine biosynthesis
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-
?
(S)-N-methylcoclaurine + NADPH + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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-
-
-
?
(S)-N-methylcoclaurine + NADPH + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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one of the key enzymes in biosynthesis of benzylisoquinoline alkaloids in the opium poppy, CYP80B1 catalyzes the second to last step in the formation of (S)-reticuline, the last common intermediate in sanguinarine and morphine biosynthesis, overview
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?
(S)-N-methylcoclaurine + NADPH + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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the catalyzes step 5 in the unique, cell type-specific biosynthesis of benzylisoquinoline alkaloids in the opium poppy, biosynthetic pathway leading from L-DOPA to morphine, overview
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-
?
(S)-N-methylcoclaurine + NADPH + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
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specific for the substrate
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-
?
additional information
?
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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additional information
?
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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-
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additional information
?
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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-
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additional information
?
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline. Accumulates in response to elicitor treatment
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
B2BF50
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-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
-
-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
-
the enzyme is involved in the sanguinarine biosynthetic pathway, overview
-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
-
-
-
-
?
(S)-N-methylcoclaurine + NADPH + H+ + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
-
the enzyme catalyzes a key regulation step in morphine biosynthesis
-
-
?
(S)-N-methylcoclaurine + NADPH + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
-
one of the key enzymes in biosynthesis of benzylisoquinoline alkaloids in the opium poppy, CYP80B1 catalyzes the second to last step in the formation of (S)-reticuline, the last common intermediate in sanguinarine and morphine biosynthesis, overview
-
-
?
(S)-N-methylcoclaurine + NADPH + O2
(S)-3'-hydroxy-N-methylcoclaurine + NADP+ + H2O
-
the catalyzes step 5 in the unique, cell type-specific biosynthesis of benzylisoquinoline alkaloids in the opium poppy, biosynthetic pathway leading from L-DOPA to morphine, overview
-
-
?
additional information
?
-
-
the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
-
-
-
additional information
?
-
-
the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
-
-
-
additional information
?
-
-
the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
-
-
-
additional information
?
-
-
the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline. Accumulates in response to elicitor treatment
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-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
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sequential treatment with methyl jasmonate, salicylic acid, and yeast extract leads to accumulation of benzophenanthridine alkaloids and increased expression of involved synthesizing enzymes, sequential treatment using different signal elicitors is more effective than single elicitor or simultaneous treatment with the elicitors, overview
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additional information
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CYP80B1 is rapidly induced to high levels in response to fungal elicitor treatment
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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localization in the sieve elements adjacent or proximal to laticifers in the root and hypocotyl of opium poppy seedlings
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root phloem, the abundance of the enzyme increases rapidly between 1 and 3 days after seed germination
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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membrane-bound, CYP80B1 from opium poppy contains a noncleavable N-terminal ER-signal peptide
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene cyp80b3, overexpression in Papaver somniferum plants, expression of anti-sense constructs, construction of transgenic plants using the Agrobacterium tumefaciens, strain AGL1, transfection method, expression of antisense cyp80b3 leads to a reduction of total alkaloid in latex up to 84%, phenotype, overview, enzyme overexpression results in an up to 450% increase in the amount of total alkaloid in latex without changing the ratio of the individual alkaloids, or together with an overall increase in the ratio of morphine
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
biotechnology
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the enzyme provides practical means to genetically engineer valuable secondary metabolites in this important medicinal plant
medicine
traditional Chinese medicinal plant containing benzylisoquinoline alkaloids as active agents
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.71)
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