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Literature summary extracted from
- Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy. (2010), Nat. Chem. Biol., 6, 273-275.
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.14.11.31 | His6-tagged protein is produced in Escherichia coli | Papaver somniferum |
| 1.14.11.32 | His6-tagged protein is produced in Escherichia coli | Papaver somniferum |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.11.31 | thebaine | - |
Papaver somniferum |  |
| 1.14.11.32 | codeine | - |
Papaver somniferum | |
| 1.14.11.32 | thebaine | - |
Papaver somniferum | |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.11.31 | 0.0154 | - |
oripavine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.31 | 0.0164 | - |
2-oxoglutarate | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.31 | 0.0203 | - |
thebaine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 0.019 | - |
2-oxoglutarate | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 0.0205 | - |
codeine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 0.0419 | - |
thebaine | pH 7.4, 30°C | Papaver somniferum | |
Metals/Ions
| EC Number | Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.11.31 | Fe2+ | required | Papaver somniferum | |
| 1.14.11.32 | Fe2+ | required | Papaver somniferum | |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.11.31 | oripavine + 2-oxoglutarate + O2 | Papaver somniferum | a step of morphine biosynthesis | morphinone + formaldehyde + succinate + CO2 | - |
? | |
| 1.14.11.31 | thebaine + 2-oxoglutarate + O2 | Papaver somniferum | a step of morphine biosynthesis | neopinone + formaldehyde + succinate + CO2 | spontaneous conversion to codeinone | ? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.11.31 | Papaver somniferum | - |
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 | - |
| 1.14.11.32 | Papaver somniferum | - |
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 | - |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 1.14.11.31 | - |
Papaver somniferum |
| 1.14.11.32 | - |
Papaver somniferum |
Reaction
| EC Number | Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|---|
| 1.14.11.31 | thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2 | spontaneous conversion of neopinione to codeinone | Papaver somniferum |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.11.31 | additional information | no activity with (S)-reticuline, (S)-scoulerine, papaverine, (S)-corytuberine, pavine, salutaridine, noscapine, codeine | Papaver somniferum | ? | - |
? | |
| 1.14.11.31 | oripavine + 2-oxoglutarate + O2 | a step of morphine biosynthesis | Papaver somniferum | morphinone + formaldehyde + succinate + CO2 | - |
? | |
| 1.14.11.31 | oripavine + 2-oxoglutarate + O2 | alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde | Papaver somniferum | morphinone + formaldehyde + succinate + CO2 | - |
? | |
| 1.14.11.31 | thebaine + 2-oxoglutarate + O2 | a step of morphine biosynthesis | Papaver somniferum | neopinone + formaldehyde + succinate + CO2 | spontaneous conversion to codeinone | ? | |
| 1.14.11.31 | thebaine + 2-oxoglutarate + O2 | 85% of the activity with oripavine. Alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde | Papaver somniferum | neopinone + formaldehyde + succinate + CO2 | spontaneous conversion to codeinone | ? | |
| 1.14.11.32 | codeine + 2-oxoglutarate + O2 | alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde | Papaver somniferum | morphine + formaldehyde + succinate + CO2 | - |
? | |
| 1.14.11.32 | additional information | no activity with (S)-reticuline, papaverine, (S)-corytuberine, pavine, salutaridine, oripavine, noscapine | Papaver somniferum | ? | - |
? | |
| 1.14.11.32 | scoulerine + 2-oxoglutarate + O2 | 120% of the activity with codeine | Papaver somniferum | 3-O-demethylscoulerine + formaldehyde + succinate + CO2 | - |
? | |
| 1.14.11.32 | thebaine + 2-oxoglutarate + O2 | 25% of the activity with codeine. Alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde | Papaver somniferum | oripavine + formaldehyde + succinate + CO2 | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.11.31 | T6ODM | - |
Papaver somniferum |
| 1.14.11.32 | codeine O-demethylase | - |
Papaver somniferum |
| 1.14.11.32 | CODM | - |
Papaver somniferum |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 1.14.11.31 | 30 | - |
assay at | Papaver somniferum |
| 1.14.11.32 | 30 | - |
assay at | Papaver somniferum |
Turnover Number [1/s]
| EC Number | Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.11.31 | 0.0081 | - |
2-oxoglutarate | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.31 | 0.017 | - |
thebaine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.31 | 0.0191 | - |
oripavine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 0.0099 | - |
thebaine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 0.011 | - |
2-oxoglutarate | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 0.0161 | - |
codeine | pH 7.4, 30°C | Papaver somniferum | |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.14.11.31 | 7.4 | - |
assay at | Papaver somniferum |
| 1.14.11.32 | 7.4 | - |
assay at | Papaver somniferum |
Ki Value [mM]
| EC Number | Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.11.31 | 0.518 | - |
thebaine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 0.642 | - |
codeine | pH 7.4, 30°C | Papaver somniferum | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.14.11.31 | malfunction | virus-induced gene silencing of T6ODM in opium poppy efficiently blocks metabolism at thebaine | Papaver somniferum |
| 1.14.11.32 | malfunction | virus-induced gene silencing of CODM in opium poppy efficiently blocks metabolism at codeine | Papaver somniferum |
kcat/KM [mM/s]
| EC Number | kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.11.31 | 492.9 | - |
2-oxoglutarate | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.31 | 837.1 | - |
thebaine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.31 | 1243 | - |
oripavine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 235.2 | - |
thebaine | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 578.9 | - |
2-oxoglutarate | pH 7.4, 30°C | Papaver somniferum | |
| 1.14.11.32 | 785.4 | - |
codeine | pH 7.4, 30°C | Papaver somniferum | |
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