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Information on EC 1.14.11.31 - thebaine 6-O-demethylase

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EC Tree

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

IUBMB Comments

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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1.14.11.31
poppy
opium
papaver
codeine
somniferum
benzylisoquinoline
o-demethylation
dioxygenases
virus-induced
acinetobacter
capsule
endophyte
reticuline
non-heme
morphinan

The enzyme appears in viruses and cellular organisms

Reaction Schemes

Synonyms

T6ODM,

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

T6ODM

T6ODM

T6ODM

700357, 725537, 743555

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2

2 entries

thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2

spontaneous conversion of neopinione to codeinone

Papaver somniferum

700357

thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2

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Go to Pathway Search

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PATHWAY SOURCE

PATHWAYS

KEGG

Biosynthesis of secondary metabolites, Isoquinoline alkaloid biosynthesis

MetaCyc

morphine biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating)

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

(R,S)-canadine + 2-oxoglutarate + O2

Papaver somniferum

a protoberberine, 32% of activity with oripavine

725537

(R,S)-tetrahydropalmatine + 2-oxoglutarate + O2

Papaver somniferum

a protoberberine, O-demethylation, below 1% of activity with oripavine

725537

(R,S)-tetrahydropapaverine + 2-oxoglutarate + O2

Papaver somniferum

a 1-benzylisoquinoline, O-demethylation, 2.1% of activity with oripavine

725537

allocryptopine + 2-oxoglutarate + O2

Papaver somniferum

a protopine, O-demethylation, 9.5% of activity with oripavine

725537

cryptopine + 2-oxoglutarate + O2

Papaver somniferum

a protopine, O-demethylation, below 1% of activity with oripavine

725537

oripavine + 2-oxoglutarate + O2

Papaver somniferum

a morphinan, best substrate

725537

oripavine + 2-oxoglutarate + O2

morphinane + formaldehyde + succinate + CO2

Papaver orientale

743439

oripavine + 2-oxoglutarate + O2

morphinone + formaldehyde + succinate + CO2

3 entries

papaverine + 2-oxoglutarate + O2

Papaver somniferum

a 1-benzylisoquinoline,O-demethylation, below 1% of activity with oripavine

725537

thebaine + 2-oxoglutarate + O2

codeinone + formaldehyde + succinate + CO2

Papaver orientale

743439

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

4 entries

additional information

2 entries

oripavine + 2-oxoglutarate + O2

morphinone + formaldehyde + succinate + CO2

Papaver somniferum

743555

oripavine + 2-oxoglutarate + O2

morphinone + formaldehyde + succinate + CO2

Papaver somniferum

a step of morphine biosynthesis

700357

oripavine + 2-oxoglutarate + O2

morphinone + formaldehyde + succinate + CO2

Papaver somniferum

alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde

700357

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

Papaver somniferum

725537, 743555

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

Papaver somniferum

a step of morphine biosynthesis

700357

spontaneous conversion to codeinone

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

Papaver somniferum

85% of the activity with oripavine. Alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde

700357

spontaneous conversion to codeinone

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

Papaver somniferum

a morphinan, 97.2% of activity with oripavine

725537

additional information

Papaver somniferum

no activity with (S)-reticuline, (S)-scoulerine, papaverine, (S)-corytuberine, pavine, salutaridine, noscapine, codeine

700357

additional information

Papaver somniferum

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

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

oripavine + 2-oxoglutarate + O2

morphinane + formaldehyde + succinate + CO2

Papaver orientale

743439

oripavine + 2-oxoglutarate + O2

morphinone + formaldehyde + succinate + CO2

2 entries

thebaine + 2-oxoglutarate + O2

codeinone + formaldehyde + succinate + CO2

Papaver orientale

743439

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

2 entries

oripavine + 2-oxoglutarate + O2

morphinone + formaldehyde + succinate + CO2

Papaver somniferum

743555

oripavine + 2-oxoglutarate + O2

morphinone + formaldehyde + succinate + CO2

Papaver somniferum

a step of morphine biosynthesis

700357

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

Papaver somniferum

725537, 743555

thebaine + 2-oxoglutarate + O2

neopinone + formaldehyde + succinate + CO2

Papaver somniferum

a step of morphine biosynthesis

700357

spontaneous conversion to codeinone

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METALS and IONS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Fe2+

Papaver somniferum

required

700357, 725537

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

thebaine

Papaver somniferum

700357

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.0164

2-oxoglutarate

Papaver somniferum

pH 7.4, 30Â°C

700357

0.0154

oripavine

Papaver somniferum

pH 7.4, 30Â°C

700357

0.0203

thebaine

Papaver somniferum

pH 7.4, 30Â°C

700357

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TURNOVER NUMBER [1/s]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.0081

2-oxoglutarate

Papaver somniferum

pH 7.4, 30Â°C

700357

0.0191

oripavine

Papaver somniferum

pH 7.4, 30Â°C

700357

0.017

thebaine

Papaver somniferum

pH 7.4, 30Â°C

700357

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kcat/KM VALUE [1/mMs^-1]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

492.9

2-oxoglutarate

Papaver somniferum

pH 7.4, 30Â°C

700357

1243

oripavine

Papaver somniferum

pH 7.4, 30Â°C

700357

837.1

thebaine

Papaver somniferum

pH 7.4, 30Â°C

700357

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Ki VALUE [mM]

INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.518

thebaine

Papaver somniferum

pH 7.4, 30Â°C

700357

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.4

Papaver somniferum

assay at

700357, 725537

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Papaver somniferum

assay at

700357, 725537

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

brenda

brenda

cv. Bea's Choice

brenda

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

700357

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

brenda

show all columns Go to General Information Search

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GENERAL INFORMATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

evolution

Papaver somniferum

the enzyme belongs to the 2-oxoglutarate/Fe(II)-dependent dioxygenase superfamily

725537

malfunction

Papaver somniferum

virus-induced gene silencing of T6ODM in opium poppy efficiently blocks metabolism at thebaine

700357

metabolism

Papaver somniferum

thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy

725537

physiological function

Papaver somniferum

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

725537

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

SEQUENCE

LOCALIZATION PREDICTION

The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).

D4N500 pBLAST

DIOX1_PAPSO

Papaver somniferum

364

40624

Swiss-Prot

Show Sequence

other Location (Reliability: 3)

A0A072U060 pBLAST

A0A072U060_MEDTR

Medicago truncatula

370

42309

TrEMBL

Show Sequence

other Location (Reliability: 4)

A0A396JBY5 pBLAST

A0A396JBY5_MEDTR

Medicago truncatula

384

44304

TrEMBL

Show Sequence

other Location (Reliability: 5)

A0A2G9GHQ2 pBLAST

A0A2G9GHQ2_9LAMI

Handroanthus impetiginosus

356

39749

TrEMBL

Show Sequence

other Location (Reliability: 3)

A0A072UFL7 pBLAST

A0A072UFL7_MEDTR

Medicago truncatula

352

40073

TrEMBL

Show Sequence

other Location (Reliability: 3)

A0A2P6Q562 pBLAST

A0A2P6Q562_ROSCH

Rosa chinensis

310

35449

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A396GMH7 pBLAST

A0A396GMH7_MEDTR

Medicago truncatula

365

41266

TrEMBL

Show Sequence

other Location (Reliability: 5)

A0A396GPI6 pBLAST

A0A396GPI6_MEDTR

Medicago truncatula

9573

TrEMBL

Show Sequence

other Location (Reliability: 4)

A0A2G9GZ15 pBLAST

A0A2G9GZ15_9LAMI

Handroanthus impetiginosus

11063

TrEMBL

Show Sequence

other Location (Reliability: 4)

A0A2G9G071 pBLAST

A0A2G9G071_9LAMI

Handroanthus impetiginosus

177

20294

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A396GMK1 pBLAST

A0A396GMK1_MEDTR

Medicago truncatula

6773

TrEMBL

Show Sequence

other Location (Reliability: 3)

A0A2G9GYU2 pBLAST

A0A2G9GYU2_9LAMI

Handroanthus impetiginosus

358

40269

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A2G9HXH5 pBLAST

A0A2G9HXH5_9LAMI

Handroanthus impetiginosus

352

39543

TrEMBL

Show Sequence

other Location (Reliability: 3)

A0A396GME6 pBLAST

A0A396GME6_MEDTR

Medicago truncatula

131

14765

TrEMBL

Show Sequence

other Location (Reliability: 3)

A0A2G9GGH5 pBLAST

A0A2G9GGH5_9LAMI

Handroanthus impetiginosus

355

40034

TrEMBL

Show Sequence

other Location (Reliability: 4)

A0A2G9GVE4 pBLAST

A0A2G9GVE4_9LAMI

Handroanthus impetiginosus

350

40260

TrEMBL

Show Sequence

other Location (Reliability: 3)

A0A396GMQ9 pBLAST

A0A396GMQ9_MEDTR

Medicago truncatula

371

42136

TrEMBL

Show Sequence

other Location (Reliability: 4)

A0A396HYT1 pBLAST

A0A396HYT1_MEDTR

Medicago truncatula

379

43699

TrEMBL

Show Sequence

Mitochondrion (Reliability: 3)

A0A396JDV8 pBLAST

A0A396JDV8_MEDTR

Medicago truncatula

334

38451

TrEMBL

Show Sequence

other Location (Reliability: 3)

A0A072TJA3 pBLAST

A0A072TJA3_MEDTR

Medicago truncatula

261

29948

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A396GYS0 pBLAST

A0A396GYS0_MEDTR

Medicago truncatula

457

52785

TrEMBL

Show Sequence

Secretory Pathway (Reliability: 4)

A0A2G9HXH1 pBLAST

A0A2G9HXH1_9LAMI

Handroanthus impetiginosus

166

18652

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A072TL01 pBLAST

A0A072TL01_MEDTR

Medicago truncatula

353

39919

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A2P6RV84 pBLAST

A0A2P6RV84_ROSCH

Rosa chinensis

301

34112

TrEMBL

Show Sequence

other Location (Reliability: 4)

A0A396GUN0 pBLAST

A0A396GUN0_MEDTR

Medicago truncatula

355

40376

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A072VFZ2 pBLAST

A0A072VFZ2_MEDTR

Medicago truncatula

358

40386

TrEMBL

Show Sequence

other Location (Reliability: 2)

A0A072UER0 pBLAST

A0A072UER0_MEDTR

Medicago truncatula

353

40116

TrEMBL

Show Sequence

other Location (Reliability: 5)

Entries 1 - 20 of 27

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PDB

SCOP

CATH

UNIPROT

ORGANISM

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PURIFICATION (Commentary)

ORGANISM

UNIPROT

LITERATURE

Papaver somniferum

700357

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

His6-tagged protein is produced in Escherichia coli

Papaver somniferum

700357

phylogenetic tree, T6ODM real time quantitative PCR expression analysis

Papaver somniferum

725537

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EXPRESSION

ORGANISM

UNIPROT

LITERATURE

endophyte SM3B (Marmoricola sp.) can enhance enzyme expression by 2.5fold

Papaver somniferum

743555

enzyme expression is significantly up-regulated with methyl jasmonate and salicylic acid treatments at 48 h

Papaver orientale

743439

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

700357

Hagel, J.M.; Facchini, P.J.

Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy.

Nat. Chem. Biol.

273-275

2010

Papaver somniferum

20228795

brenda

725537

Farrow, S.C.; Facchini, P.J.

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

J. Biol. Chem.

288

28997-29012

2013

Papaver somniferum

23928311

brenda

743439

Hashemi, S.; Naghavi, M.

Production and gene expression of morphinan alkaloids in hairy root culture of Papaver orientale L. using abiotic elicitors

Plant Cell

125

31-41

2016

Papaver orientale

brenda

743555

Pandey, S.S.; Singh, S.; Babu, C.S.; Shanker, K.; Srivastava, N.K.; Kalra, A.

Endophytes of opium poppy differentially modulate host plant productivity and genes for the biosynthetic pathway of benzylisoquinoline alkaloids

Planta

243

1097-1114

2016

Papaver somniferum

26794966

brenda

Entries 1 - 20 of 4

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EXTERNAL LINKS (specific for EC-Number 1.14.11.31)

ExplorEnz (official portal for IUBMB Enzyme Nomenclature)

Expasy Enzyme Nomenclature Database

KEGG

MetaCyc

SABIO-RK

NCBI: PubMed, Protein, Nucleotide, Structure, Gene, OMIM

Enzyme Nomenclature (alternative site)

UniProt

PDB

PROSITE Database of protein families and domains

InterPro (database of protein families, domains and functional sites)

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