KEGG   ORTHOLOGY: K14976
Entry
K14976            Tight     KO                                     
Symbol
T6ODM
Name
thebaine 6-O-demethylase [EC:1.14.11.31]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00944  Morphine biosynthesis, (S)-reticuline => morphine
Reaction
R03698  oripavine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating)
R05126  thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K14976  T6ODM; thebaine 6-O-demethylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.11  With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
    1.14.11.31  thebaine 6-O-demethylase
     K14976  T6ODM; thebaine 6-O-demethylase
Other DBs
GO: 0102802
Genes
PSOM: 113272570 113347785 113347786 113347787 113347789 113347790
AG: ADD85329(T6ODM)
Reference
PMID:20228795
  Authors
Hagel JM, Facchini PJ
  Title
Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy.
  Journal
Nat Chem Biol 6:273-5 (2010)
DOI:10.1038/nchembio.317
  Sequence
[ag:ADD85329]
LinkDB

KEGG   ENZYME: 1.14.11.31
Entry
EC 1.14.11.31               Enzyme                                 
Name
thebaine 6-O-demethylase;
T6ODM
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
Sysname
thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating)
Reaction(IUBMB)
thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2 [RN:R05126]
Reaction(KEGG)
R05126;
(other) R03698
Substrate
thebaine [CPD:C06173];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]
Product
neopinone [CPD:C06172];
formaldehyde [CPD:C00067];
succinate [CPD:C00042];
CO2 [CPD:C00011]
Comment
Requires Fe2+. Catalyses a step in morphine biosynthesis. The product neopinione spontaneously rearranges to the more stable codeinone. The enzyme also catalyses the 6-O-demethylation of oripavine to morphinone, with lower efficiency.
History
EC 1.14.11.31 created 2010
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14976  thebaine 6-O-demethylase
Genes
PSOM: 113272570 113347785 113347786 113347787 113347789 113347790
Reference
1  [PMID:20228795]
  Authors
Hagel JM, Facchini PJ
  Title
Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy.
  Journal
Nat Chem Biol 6:273-5 (2010)
DOI:10.1038/nchembio.317
  Sequence
[ag:ADD85329]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.11.31
IUBMB Enzyme Nomenclature: 1.14.11.31
ExPASy - ENZYME nomenclature database: 1.14.11.31
BRENDA, the Enzyme Database: 1.14.11.31
LinkDB

KEGG   REACTION: R05126
Entry
R05126                      Reaction                               
Name
thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating)
Definition
Thebaine + 2-Oxoglutarate + Oxygen <=> Neopinone + Formaldehyde + Succinate + CO2
Equation
C06173 + C00026 + C00007 <=> C06172 + C00067 + C00042 + C00011
Reaction class
RC01994  C06172_C06173
RC02542  C00067_C06173
Enzyme
1.14.11.31
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.11  With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
    1.14.11.31
     R05126  Thebaine + 2-Oxoglutarate + Oxygen <=> Neopinone + Formaldehyde + Succinate + CO2
Orthology
K14976  thebaine 6-O-demethylase [EC:1.14.11.31]
Other DBs
RHEA: 27480
LinkDB

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