KEGG   ORTHOLOGY: K13394
Entry
K13394                      KO                                     
Symbol
COR1
Name
codeinone reductase [EC:1.1.1.247]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00944  Morphine biosynthesis, (S)-reticuline => morphine
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K13394  COR1; codeinone reductase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.247  codeinone reductase (NADPH)
     K13394  COR1; codeinone reductase
Other DBs
RN: R03592 R05124
GO: 0047036
Genes
MING: 122080318
PSOM: 113293958 113294469 113328200 113328201
AG: AAF13736(COR1)
Reference
PMID:10417697
  Authors
Unterlinner B, Lenz R, Kutchan TM
  Title
Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum.
  Journal
Plant J 18:465-75 (1999)
DOI:10.1046/j.1365-313X.1999.00470.x
  Sequence
[ag:AAF13736]
LinkDB

KEGG   ORTHOLOGY: K03378
Entry
K03378            Tight     KO                                     
Symbol
morA
Name
morphine 6-dehydrogenase [EC:1.1.1.218]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K03378  morA; morphine 6-dehydrogenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.218  morphine 6-dehydrogenase
     K03378  morA; morphine 6-dehydrogenase
Other DBs
RN: R03591 R03592
GO: 0050109
Genes
AG: AAB17356(morA)
Reference
PMID:8452544
  Authors
Willey DL, Caswell DA, Lowe CR, Bruce NC
  Title
Nucleotide sequence and over-expression of morphine dehydrogenase, a plasmid-encoded gene from Pseudomonas putida M10.
  Journal
Biochem J 290 ( Pt 2):539-44 (1993)
DOI:10.1042/bj2900539
  Sequence
[ag:AAB17356]
LinkDB

KEGG   ENZYME: 1.1.1.218
Entry
EC 1.1.1.218                Enzyme                                 
Name
morphine 6-dehydrogenase;
naloxone reductase
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
morphine:NAD(P)+ 6-oxidoreductase
Reaction(IUBMB)
morphine + NAD(P)+ = morphinone + NAD(P)H + H+ [RN:R03591 R03592]
Reaction(KEGG)
R03591 R03592
Substrate
morphine [CPD:C01516];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006]
Product
morphinone [CPD:C01735];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
Also acts on some other alkaloids, including codeine, normorphine and ethylmorphine, but only very slowly on 7,8-saturated derivatives such as dihydromorphine and dihydrocodeine. In the reverse direction, also reduces naloxone to the 6alpha-hydroxy analogue. Activated by 2-sulfanylethan-1-ol (2-mercaptoethanol).
History
EC 1.1.1.218 created 1989, modified 1990
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K03378  morphine 6-dehydrogenase
K13374  aldo-keto reductase family 1 member C13
Genes
MMU: 27384(Akr1c13) 622402(Akr1c12)
MCAL: 110288103
MPAH: 110333723
RNO: 361266(Akr1c13)
CGE: 100769523
NGI: 103725887
CCAN: 109680003
DORD: 105980361 105980413 105980416 105980418
DSP: 122113029
Reference
1  [PMID:2580834]
  Authors
Yamano S, Kageura E, Ishida T, Toki S.
  Title
Purification and characterization of guinea pig liver morphine 6-dehydrogenase.
  Journal
J Biol Chem 260:5259-64 (1985)
Reference
2  [PMID:3539118]
  Authors
Yamano S, Nishida F, Toki S.
  Title
Guinea-pig liver morphine 6-dehydrogenase as a naloxone reductase.
  Journal
Biochem Pharmacol 35:4321-6 (1986)
DOI:10.1016/0006-2952(86)90712-4
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.218
IUBMB Enzyme Nomenclature: 1.1.1.218
ExPASy - ENZYME nomenclature database: 1.1.1.218
BRENDA, the Enzyme Database: 1.1.1.218
CAS: 97002-71-6
LinkDB

KEGG   ENZYME: 1.1.1.247
Entry
EC 1.1.1.247                Enzyme                                 
Name
codeinone reductase (NADPH)
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
codeine:NADP+ oxidoreductase
Reaction(IUBMB)
codeine + NADP+ = codeinone + NADPH + H+ [RN:R05124]
Reaction(KEGG)
R05124;
(other) R03592
Substrate
codeine [CPD:C06174];
NADP+ [CPD:C00006]
Product
codeinone [CPD:C06171];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
History
EC 1.1.1.247 created 1999, modified 2001
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13394  codeinone reductase
Genes
MING: 122080318
PSOM: 113293958 113294469 113328200 113328201
Reference
1
  Authors
Lenz, R. and Zenk, M.H.
  Title
Stereoselective reduction of codeinone, the penultimate step during morphine biosynthesis in Papaver somniferum.
  Journal
Tetrahedron Lett 36:2449-2452 (1995)
Reference
2  [PMID:7588736]
  Authors
Lenz R, Zenk MH.
  Title
Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures and differentiated plants.
  Journal
Eur J Biochem 233:132-9 (1995)
DOI:10.1111/j.1432-1033.1995.132_1.x
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.247
IUBMB Enzyme Nomenclature: 1.1.1.247
ExPASy - ENZYME nomenclature database: 1.1.1.247
BRENDA, the Enzyme Database: 1.1.1.247
CAS: 153302-41-1
LinkDB

KEGG   REACTION: R03591
Entry
R03591                      Reaction                               
Name
morphine:NAD+ 6-oxidoreductase
Definition
Morphine + NAD+ <=> Morphinone + NADH + H+
Equation
C01516 + C00003 <=> C01735 + C00004 + C00080
Comment
NADP+ (see R03592)
Reaction class
RC00001  C00003_C00004
RC00206  C01516_C01735
Enzyme
1.1.1.218
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Orthology
K03378  morphine 6-dehydrogenase [EC:1.1.1.218]
Other DBs
RHEA: 14320
LinkDB

KEGG   REACTION: R03592
Entry
R03592                      Reaction                               
Name
morphine:NAD(P)+ 6-oxidoreductase
Definition
Morphine + NADP+ <=> Morphinone + NADPH + H+
Equation
C01516 + C00006 <=> C01735 + C00005 + C00080
Comment
NAD+ (see R03591)
Reaction class
RC00001  C00005_C00006
RC00206  C01516_C01735
Enzyme
1.1.1.218       1.1.1.247
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00944  Morphine biosynthesis, (S)-reticuline => morphine
Orthology
K03378  morphine 6-dehydrogenase [EC:1.1.1.218]
K13394  codeinone reductase [EC:1.1.1.247]
Other DBs
RHEA: 14324
LinkDB

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