Information on EC 1.1.1.247 - codeinone reductase (NADPH)

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.247
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RECOMMENDED NAME
GeneOntology No.
codeinone reductase (NADPH)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
codeine + NADP+ = codeinone + NADPH + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
morphine biosynthesis
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Isoquinoline alkaloid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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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.
CAS REGISTRY NUMBER
COMMENTARY hide
153302-41-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
Codeinone + NADPH
Codeine + NADP+
show the reaction diagram
codeinone + NADPH + H+
codeine + NADP+
show the reaction diagram
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-
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r
Dihydrocodeine + NADP+
?
show the reaction diagram
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-
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Hydrocodone + NADPH
?
show the reaction diagram
Hydromorphone + NADPH
?
show the reaction diagram
Morphinone + NADPH
Morphine + NADP+
show the reaction diagram
Naloxone + NADPH
?
show the reaction diagram
Naltrexone + NADPH
?
show the reaction diagram
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
Codeinone + NADPH
Codeine + NADP+
show the reaction diagram
codeinone + NADPH + H+
codeine + NADP+
show the reaction diagram
Q9SQ67
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r
Morphinone + NADPH
Morphine + NADP+
show the reaction diagram
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biosynthesis of morphine
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additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.076 - 0.178
codeine
0.009 - 0.023
codeinone
0.422 - 0.424
Dihydrocodeine
0.026 - 0.027
Hydrocodone
0.042 - 0.05
Hydromorphone
0.063
morphine
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isoenzymes from capsule tissue
0.029 - 0.047
NADP+
0.081 - 0.168
NADPH
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
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reduction of codeinone
9.1
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oxidation of codeine
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
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
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
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reduction of codeinone
46
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oxidation of codeine
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
29 - 47
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50% of maximal activity at 29C and 47C, reduction of codeinone
34 - 53
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50% of maximal activity at 34C and 53C, oxidation of codeine
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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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
Manually annotated by BRENDA team
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localized in laticifers
Manually annotated by BRENDA team
additional information
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laticifers are not found in developing root tip, and likewise, codeinone reductase is not detected
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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34000-35000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2 isoenzymes from capsule tissue, enzyme from cell culture
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Ni2+-charged HiTrap column chromatography
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Ni21-charged HiTrap column chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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 hide
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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
Papaver bracteatum hairy roots expressing CodR gene have a high potential to produce morphinan alkaloids