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Enzyme Nomenclature
Information on EC 1.1.1.247 - codeinone reductase (NADPH)
Word Map on EC 1.1.1.247
- 1.1.1.247
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alkaloid
- morphine
- somniferum
- poppy
- papaver
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opium
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narcotic
- berberine
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morphinans
-
benzylisoquinoline
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penultimate
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analgesics
- thebaine
- cyp80b1
- sanguinarine
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latex
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s-n-methylcoclaurine
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laticifer
-
3'-hydroxylase
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elicitor
- salutaridinol
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s-reticuline
- chalcone
-
6-o-methyltransferase
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antitussive
- bracteatum
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aldo-keto
- n-methyltransferase
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semi-synthetic
- synthesis
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.1.1.247
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RECOMMENDED NAME
GeneOntology No.
codeinone reductase (NADPH)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
codeine + NADP+ = codeinone + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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reduction
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
codeine:NADP+ oxidoreductase
Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
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CAS REGISTRY NUMBER
COMMENTARY
153302-41-1
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
Codeinone + NADPH
Codeine + NADP+
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no reaction with NADH and NAD+
(-)codeine
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Codeinone + NADPH
Codeine + NADP+
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neopinone, which is formed most likely by demethylation of the vinylether of thebaine exists in the plant cell in a thermodynamic equilibrium with codeinone. The presence of the codeinone reductase/NADPH system shifts this equilibrium quantitatively in the direction of codeine, which either accumulates in the latex of the poppy plant or is further demethylated at the 3-OCH3 group yielding morphine
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Codeinone + NADPH
Codeine + NADP+
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important regulating function in morphine biosynthesis
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Codeinone + NADPH
Codeine + NADP+
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penultimate step in morphine biosynthesis
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r
additional information
?
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the enzyme is involved in biosynthesis of morphinan alkaloids, transcriptional regulation, overview
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-
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additional information
?
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the enzyme is involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine
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additional information
?
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the enzyme is involved in biosynthesis of morphinan alkaloids, overview
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additional information
?
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the enzyme also catalyzes the NADPH-dependent reduction of morphinone to morphine, reaction of EC 1.1.1.218. but codeine can also be directly converted into morphine, overview
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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
Codeinone + NADPH
Codeine + NADP+
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neopinone, which is formed most likely by demethylation of the vinylether of thebaine exists in the plant cell in a thermodynamic equilibrium with codeinone. The presence of the codeinone reductase/NADPH system shifts this equilibrium quantitatively in the direction of codeine, which either accumulates in the latex of the poppy plant or is further demethylated at the 3-OCH3 group yielding morphine
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Codeinone + NADPH
Codeine + NADP+
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important regulating function in morphine biosynthesis
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Codeinone + NADPH
Codeine + NADP+
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penultimate step in morphine biosynthesis
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-
r
additional information
?
-
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the enzyme is involved in biosynthesis of morphinan alkaloids, transcriptional regulation, overview
-
-
-
additional information
?
-
-
the enzyme is involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine
-
-
-
additional information
?
-
-
the enzyme is involved in biosynthesis of morphinan alkaloids, overview
-
-
-
additional information
?
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Q9SQ67
the enzyme also catalyzes the NADPH-dependent reduction of morphinone to morphine, reaction of EC 1.1.1.218. but codeine can also be directly converted into morphine, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
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10-100fold increase in enzyme activity of enzymes involved in the biosynthesis of morphinan alkaloids by overexpression of regulatory transcription factors, overview
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additional information
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10-100fold increase in enzyme activity of enzymes involved in the biosynthesis of morphinan alkaloids by overexpression of regulatory transcription factors, overview
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.027
Hydrocodone
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enzyme from cell culture; morphine, enzyme from cell culture
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.2 - 7.6
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50% of maximal activity at pH 6.2 and pH 7.6, reduction of codeinone
8.2 - 9.8
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50% of maximal activity at pH 8.2 and pH 9.8, oxidation of codeine
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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high expression. Peaks of transcription in the capsules wall are at flowering
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localization is restricted to the parietal region of sieve elements adjacent or proximal to laticifers. COR transcript is found in the companion cell paired with each sieve element
additional information
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laticifers are not found in developing root tip, and likewise, codeinone reductase is not detected
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high expression. The expression increases until pre-flowering and then decreases
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high expression. Relative expression has two peaks at bud initiation, the maximum rate, and flowering stages
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high expression in upper stem. Peaks of expression are at flowering and lancing
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
factors involved in transcriptional regulation, overview
gene codR, expression in Papaver bracteatum in cultured hairy roots, subcloning in Escherichia coli strain DH5alpha. The T-DNA of the vector contains a neomycin phosphoteransferase gene and CodR cDNA with CaMV35S promoter and nos terminator
overexpression of the enzyme in transgenic Papaver somnniferum plants leading to increased enzyme content and capsule alkaloid, morphine and total alkaloid, content without significant alterations of the alkaloid profile, overview
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
transgenic codeinone reductase overexpressing Papaver somniferum plants show 75% increase in thebaine besides 58% and 22% increases in codeine and morphine, respectively, compared to the wild-type plants in the field trail
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
Papaver bracteatum hairy roots expressing CodR gene have a high potential to produce morphinan alkaloids
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.247)
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