BRENDA home
History
Information on EC 1.1.1.247 - codeinone reductase (NADPH)
for references in articles please use BRENDA:EC1.1.1.247Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
1.1.1.247 codeinone reductase (NADPH)IUBMB Comments
Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
Specify your search results
Word Map
- 1.1.1.247
- morphine
- papaver
- poppy
- somniferum
-
opium
-
benzylisoquinoline
-
narcotic
- thebaine
-
morphinans
- berberine
-
penultimate
- sanguinarine
- chalcone
-
analgesics
- cyp80b1
-
3\'-hydroxylase
- salutaridinol
- latex
- bracteatum
-
s-n-methylcoclaurine
-
laticifer
-
7-o-acetyltransferase
-
s-reticuline
-
aldo-keto
-
4\'omt
- norcoclaurine
-
antitussive
-
6-o-methyltransferase
- o-demethylase
- synthesis
The enzyme appears in viruses and cellular organisms
Synonyms
codeine oxidase, codeine: NADP oxidoreductase, codeine:NADP oxidoreductase, codeinone reductase, codeinone reductase (NADPH), CodR, COR, PsCor1.1, reductase, codeinone (reduced nicotinamide adenine dinucleotide phosphate), 
more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
codeine oxidase
-
-
-
-
codeine: NADP oxidoreductase
-
-
-
-
codeine:NADP oxidoreductase
-
-
-
-
codeinone reductase
COR
reductase, codeinone (reduced nicotinamide adenine dinucleotide phosphate)
-
-
-
-
codeinone reductase
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
codeine + NADP+ = codeinone + NADPH + H+
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
MetaCyc
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
153302-41-1
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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+
-
no reaction with NADH and NAD+
(-)codeine
?
Codeinone + NADPH
Codeine + NADP+
-
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
-
-
?
Codeinone + NADPH
Codeine + NADP+
-
important regulating function in morphine biosynthesis
-
-
?
Codeinone + NADPH
Codeine + NADP+
-
penultimate step in morphine biosynthesis
-
-
r
additional information
?
-
-
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
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL 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+
-
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
-
-
?
Codeinone + NADPH
Codeine + NADP+
-
important regulating function in morphine biosynthesis
-
-
?
Codeinone + NADPH
Codeine + NADP+
-
penultimate step in morphine biosynthesis
-
-
r
additional information
?
-
-
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
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
10-100fold increase in enzyme activity of enzymes involved in the biosynthesis of morphinan alkaloids by overexpression of regulatory transcription factors, overview
-
additional information
-
10-100fold increase in enzyme activity of enzymes involved in the biosynthesis of morphinan alkaloids by overexpression of regulatory transcription factors, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.2 - 7.6
-
50% of maximal activity at pH 6.2 and pH 7.6, reduction of codeinone
8.2 - 9.8
-
50% of maximal activity at pH 8.2 and pH 9.8, oxidation of codeine
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
29 - 47
-
50% of maximal activity at 29°C and 47°C, reduction of codeinone
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
high expression. Peaks of transcription in the capsules wall are at flowering
brenda
-
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
brenda
additional information
-
laticifers are not found in developing root tip, and likewise, codeinone reductase is not detected
brenda
-
high expression. The expression increases until pre-flowering and then decreases
brenda
-
high expression. Relative expression has two peaks at bud initiation, the maximum rate, and flowering stages
brenda
-
high expression in upper stem. Peaks of expression are at flowering and lancing
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). COR11_PAPSO
321
0
35808
Swiss-Prot
other Location (Reliability: 2)
COR12_PAPSO
321
0
35705
Swiss-Prot
other Location (Reliability: 2)
COR13_PAPSO
321
0
35797
Swiss-Prot
other Location (Reliability: 2)
COR14_PAPSO
321
0
35764
Swiss-Prot
other Location (Reliability: 2)
COR15_PAPSO
321
0
35794
Swiss-Prot
other Location (Reliability: 2)
A0A2P6R4C7_ROSCH
48
0
5298
TrEMBL
other Location (Reliability: 5)
Q9SQ65_PAPSO
97
0
10913
TrEMBL
Secretory Pathway (Reliability: 5)
Q9SQ66_PAPSO
51
0
5637
TrEMBL
other Location (Reliability: 5)
A0A2G9HUU1_9LAMI
273
0
30259
TrEMBL
other Location (Reliability: 4)
A0A2I6ZMS8_PAPSO
321
0
35784
TrEMBL
other Location (Reliability: 2)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
UNIPROT
ORGANISM
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
Papaver bracteatum hairy roots expressing CodR gene have a high potential to produce morphinan alkaloids
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lenz, R.; Zenk, M.H.
Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures and differentiated plants
Eur. J. Biochem.
233
132-139
1995
Papaver somniferum
brenda
Gollwitzer, J.; Lenz, R.; Hampp, N.; Zenk, M.H.
The transformation of neopinone to codeinone in morphine biosynthesis proceeds non-enzymatically
Tetrahedron Lett.
34
5703-5706
1993
Papaver somniferum
-
brenda
Lenz, R.; Zenk, M.H.
Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum
Tetrahedron Lett.
36
2449-2452
1995
Papaver somniferum
-
brenda
Bird, D.A.; Franceschi, V.R.; Facchini, P.J.
A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy
Plant Cell
15
2626-2635
2003
Papaver somniferum
brenda
Weid, M.; Ziegler, J.; Kutchan, T.M.
The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum
Proc. Natl. Acad. Sci. USA
101
13957-13962
2004
Papaver somniferum
brenda
Alcantara, J.; Bird, D.A.; Franceschi, V.R.; Facchini, P.J.
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment
Plant Physiol.
138
173-183
2005
Papaver somniferum (Q9SQ70), Papaver somniferum
brenda
Samanani, N.; Alcantara, J.; Bourgault, R.; Zulak, K.G.; Facchini, P.J.
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy
Plant J.
47
547-563
2006
Papaver somniferum
brenda
Ziegler, J.; Voigtlaender, S.; Schmidt, J.; Kramell, R.; Miersch, O.; Ammer, C.; Gesell, A.; Kutchan, T.M.
Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis
Plant J.
48
177-192
2006
Papaver somniferum
brenda
Larkin, P.J.; Miller, J.A.; Allen, R.S.; Chitty, J.A.; Gerlach, W.L.; Frick, S.; Kutchan, T.M.; Fist, A.J.
Increasing morphinan alkaloid production by over-expressing codeinone reductase in transgenic Papaver somniferum
Plant Biotechnol. J.
5
26-37
2007
Papaver somniferum
brenda
Apuya, N.R.; Park, J.H.; Zhang, L.; Ahyow, M.; Davidow, P.; Van Fleet, J.; Rarang, J.C.; Hippley, M.; Johnson, T.W.; Yoo, H.D.; Trieu, A.; Krueger, S.; Wu, C.Y.; Lu, Y.P.; Flavell, R.B.; Bobzin, S.C.
Enhancement of alkaloid production in opium and California poppy by transactivation using heterologous regulatory factors
Plant Biotechnol. J.
6
160-175
2008
Eschscholzia californica, Papaver somniferum
brenda
Sharafi, A.; Sohi, H.H.; Mousavi, A.; Azadi, P.; Khalifani, B.H.; Razavi, K.
Metabolic engineering of morphinan alkaloids by over-expression of codeinone reductase in transgenic hairy roots of Papaver bracteatum, the Iranian poppy
Biotechnol. Lett.
35
445-453
2013
Papaver somniferum (Q9SQ67), Papaver somniferum
brenda
Rezaei, M.; Naghavi, M.; Hoseinzade, A.; Abbasi, A.
Developmental accumulation of thebaine and some gene transcripts in different organs of Papaver bracteatum
Ind. Crops Prod.
80
262-268
2016
Papaver bracteatum
-
brenda
Alagöz, Y.; Gürkök, T.; Parmaksiz, I.; Ünver, T.
Identification and sequence analysis of alkaloid biosynthesis genes in papaver section oxytona
Turk. J. Biol.
40
174-183
2016
Papaver pseudo-orientale (A0A0H4BJ99)
-
brenda
Select items on the left to see more content.
EXTERNAL LINKS (specific for EC-Number 1.1.1.247)
html completed
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
About BRENDA
Help
Download
Contribution
member of
curated at
curated at
Server: brenda4 Ver: 9edf756-main (2022-05-17 10:30:03 +0200)