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Enzyme Nomenclature
Information on EC 1.14.11.31 - thebaine 6-O-demethylase
for references in articles please use BRENDA:EC1.14.11.31
Word Map on EC 1.14.11.31
- 1.14.11.31
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opium
- poppy
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alkaloids
- codeine
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papaver
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dioxygenases
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benzylisoquinoline
- somniferum
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virus-induced
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o-demethylation
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non-heme
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The expected taxonomic range for this enzyme is: Papaver
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EC NUMBER 
COMMENTARY 
1.14.11.31
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RECOMMENDED NAME
GeneOntology No.
thebaine 6-O-demethylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2
spontaneous conversion of neopinione to codeinone
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thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating)
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.
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
high-morphine varieties (i.e. L, 11 and 40) and a mutant variety (i.e. T) that accumulates high levels of thebaine and oripavine, but lacks morphine and codeine
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
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the enzyme belongs to the 2-oxoglutarate/Fe(II)-dependent dioxygenase superfamily
malfunction
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virus-induced gene silencing of T6ODM in opium poppy efficiently blocks metabolism at thebaine
metabolism
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thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy
physiological function
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thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy, but has also roles in the metabolism of protopine, benzo[c]phenanthridine, and rhoeadine alkaloids
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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
(R,S)-canadine + 2-oxoglutarate + O2
?
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a protoberberine, 32% of activity with oripavine
-
-
?
(R,S)-tetrahydropalmatine + 2-oxoglutarate + O2
?
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a protoberberine, O-demethylation, below 1% of activity with oripavine
-
-
?
(R,S)-tetrahydropapaverine + 2-oxoglutarate + O2
?
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a 1-benzylisoquinoline, O-demethylation, 2.1% of activity with oripavine
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-
?
allocryptopine + 2-oxoglutarate + O2
?
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a protopine, O-demethylation, 9.5% of activity with oripavine
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-
?
cryptopine + 2-oxoglutarate + O2
?
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a protopine, O-demethylation, below 1% of activity with oripavine
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-
?
oripavine + 2-oxoglutarate + O2
morphinane + formaldehyde + succinate + CO2
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-
-
-
?
papaverine + 2-oxoglutarate + O2
?
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a 1-benzylisoquinoline,O-demethylation, below 1% of activity with oripavine
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-
?
thebaine + 2-oxoglutarate + O2
codeinone + formaldehyde + succinate + CO2
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-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
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-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
-
a step of morphine biosynthesis
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-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
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alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde
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-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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-
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
-
a step of morphine biosynthesis
spontaneous conversion to codeinone
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?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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85% of the activity with oripavine. Alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde
spontaneous conversion to codeinone
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?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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a morphinan, 97.2% of activity with oripavine
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-
?
additional information
?
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no activity with (S)-reticuline, (S)-scoulerine, papaverine, (S)-corytuberine, pavine, salutaridine, noscapine, codeine
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additional information
?
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when assayed with a wide range of benzylisoquinoline alkaloids, the enzyme shows efficient dealkylation activities, including regio- and substrate-specific O-demethylation and O,O-demethylenation, substrate specificity, overview. No or poor activity with (S)-reticuline, (S)-isocorydine, (S)-scoulerine, (R,S)-stylopine, berberine, O-demethylcryptopine, protopine, and codeine
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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
oripavine + 2-oxoglutarate + O2
morphinane + formaldehyde + succinate + CO2
-
-
-
-
?
thebaine + 2-oxoglutarate + O2
codeinone + formaldehyde + succinate + CO2
-
-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
-
-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
-
a step of morphine biosynthesis
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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-
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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a step of morphine biosynthesis
spontaneous conversion to codeinone
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?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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PDB
SCOP
CATH
ORGANISM
UNIPROT
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
endophyte SM3B (Marmoricola sp.) can enhance enzyme expression by 2.5fold
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enzyme expression is significantly up-regulated with methyl jasmonate and salicylic acid treatments at 48 h
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.11.31)
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