BRENDA - Enzyme Database
show all sequences of 1.14.11.31

Dioxygenases catalyze O-demethylation and O,O-demethylenation with widespread roles in benzylisoquinoline alkaloid metabolism in opium poppy

Farrow, S.C.; Facchini, P.J.; J. Biol. Chem. 288, 28997-29012 (2013)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
phylogenetic tree, T6ODM real time quantitative PCR expression analysis
Papaver somniferum
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Fe2+
required
Papaver somniferum
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
thebaine + 2-oxoglutarate + O2
Papaver somniferum
-
neopinone + formaldehyde + succinate + CO2
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Papaver somniferum
-
cv. Bea's Choice
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
(R,S)-canadine + 2-oxoglutarate + O2
a protoberberine, 32% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
(R,S)-tetrahydropalmatine + 2-oxoglutarate + O2
a protoberberine, O-demethylation, below 1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
(R,S)-tetrahydropapaverine + 2-oxoglutarate + O2
a 1-benzylisoquinoline, O-demethylation, 2.1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
allocryptopine + 2-oxoglutarate + O2
a protopine, O-demethylation, 9.5% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
cryptopine + 2-oxoglutarate + O2
a protopine, O-demethylation, below 1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
additional information
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
725537
Papaver somniferum
?
-
-
-
?
oripavine + 2-oxoglutarate + O2
a morphinan, best substrate
725537
Papaver somniferum
?
-
-
-
?
papaverine + 2-oxoglutarate + O2
a 1-benzylisoquinoline,O-demethylation, below 1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
thebaine + 2-oxoglutarate + O2
-
725537
Papaver somniferum
neopinone + formaldehyde + succinate + CO2
-
-
-
?
thebaine + 2-oxoglutarate + O2
a morphinan, 97.2% of activity with oripavine
725537
Papaver somniferum
neopinone + formaldehyde + succinate + CO2
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
T6ODM
-
Papaver somniferum
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
assay at
Papaver somniferum
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.4
-
assay at
Papaver somniferum
Cloned(Commentary) (protein specific)
Commentary
Organism
phylogenetic tree, T6ODM real time quantitative PCR expression analysis
Papaver somniferum
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Fe2+
required
Papaver somniferum
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
thebaine + 2-oxoglutarate + O2
Papaver somniferum
-
neopinone + formaldehyde + succinate + CO2
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
(R,S)-canadine + 2-oxoglutarate + O2
a protoberberine, 32% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
(R,S)-tetrahydropalmatine + 2-oxoglutarate + O2
a protoberberine, O-demethylation, below 1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
(R,S)-tetrahydropapaverine + 2-oxoglutarate + O2
a 1-benzylisoquinoline, O-demethylation, 2.1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
allocryptopine + 2-oxoglutarate + O2
a protopine, O-demethylation, 9.5% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
cryptopine + 2-oxoglutarate + O2
a protopine, O-demethylation, below 1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
additional information
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
725537
Papaver somniferum
?
-
-
-
?
oripavine + 2-oxoglutarate + O2
a morphinan, best substrate
725537
Papaver somniferum
?
-
-
-
?
papaverine + 2-oxoglutarate + O2
a 1-benzylisoquinoline,O-demethylation, below 1% of activity with oripavine
725537
Papaver somniferum
?
-
-
-
?
thebaine + 2-oxoglutarate + O2
-
725537
Papaver somniferum
neopinone + formaldehyde + succinate + CO2
-
-
-
?
thebaine + 2-oxoglutarate + O2
a morphinan, 97.2% of activity with oripavine
725537
Papaver somniferum
neopinone + formaldehyde + succinate + CO2
-
-
-
?
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
assay at
Papaver somniferum
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.4
-
assay at
Papaver somniferum
General Information
General Information
Commentary
Organism
evolution
the enzyme belongs to the 2-oxoglutarate/Fe(II)-dependent dioxygenase superfamily
Papaver somniferum
metabolism
thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy
Papaver somniferum
physiological function
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
Papaver somniferum
General Information (protein specific)
General Information
Commentary
Organism
evolution
the enzyme belongs to the 2-oxoglutarate/Fe(II)-dependent dioxygenase superfamily
Papaver somniferum
metabolism
thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy
Papaver somniferum
physiological function
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
Papaver somniferum
Other publictions for EC 1.14.11.31
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
743439
Hashemi
-
Production and gene expressio ...
Papaver orientale
Plant Cell
125
31-41
2016
-
-
-
-
-
-
-
-
-
-
-
2
-
1
-
-
-
-
-
1
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2
-
1
-
-
-
-
-
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-
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-
-
2
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
743555
Pandey
Endophytes of opium poppy dif ...
Papaver somniferum
Planta
243
1097-1114
2016
-
-
-
-
-
-
-
-
-
-
-
2
-
3
-
-
-
-
-
-
-
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2
-
1
-
-
-
-
-
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-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
725537
Farrow
Dioxygenases catalyze O-demeth ...
Papaver somniferum
J. Biol. Chem.
288
28997-29012
2013
-
-
1
-
-
-
-
-
-
1
-
1
-
4
-
-
-
-
-
-
-
-
10
-
1
1
-
-
-
1
-
-
-
-
-
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-
-
1
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
10
-
1
-
-
-
1
-
-
-
-
3
3
-
-
-
700357
Hagel
Dioxygenases catalyze the O-de ...
Papaver somniferum
Nat. Chem. Biol.
6
273-275
2010
-
-
1
-
-
-
1
3
-
1
-
2
-
4
-
-
1
1
-
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5
-
1
1
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3
1
-
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1
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1
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1
1
3
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1
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2
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1
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5
-
1
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3
1
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1
1
-
3
3