Information on EC 1.14.14.97 - methyltetrahydroprotoberberine 14-monooxygenase

for references in articles please use BRENDA:EC1.14.14.97

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EC Tree 1 Oxidoreductases 1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen 1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor 1.14.14.97 methyltetrahydroprotoberberine 14-monooxygenase

IUBMB Comments

A cytochrome P-450 (heme-thiolate) protein found in plants.

The enzyme appears in viruses and cellular organisms

Reaction Schemes

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(S)-N-methylcanadine

[reduced NADPH-hemoprotein reductase]

allocryptopine

[oxidized NADPH-hemoprotein reductase]

H2O

Synonyms
(S)-cis-N-methyltetrahydroprotoberberine-14-hydroxylase, EC 1.14.13.37, methyltetrahydroprotoberberine 14-hydroxylase, oxygenase, (S)-cis-N-methyltetrahydroberberine 14-mono-, more

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

(S)-cis-N-methyltetrahydroprotoberberine-14-hydroxylase

EC 1.14.13.37

formerly

methyltetrahydroprotoberberine 14-hydroxylase

oxygenase, (S)-cis-N-methyltetrahydroberberine 14-mono-

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

(S)-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 = allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

2 entries

(S)-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 = allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

stereo- and regiospecificity

Corydalis vaginans

285317

(S)-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 = allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

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REACTION TYPE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

oxidation

redox reaction

reduction

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Go to Pathway Search

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PATHWAY SOURCE

PATHWAYS

KEGG

Biosynthesis of secondary metabolites, Isoquinoline alkaloid biosynthesis

MetaCyc

chelerythrine biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

(S)-N-methylcanadine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating)

A cytochrome P-450 (heme-thiolate) protein found in plants.

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CAS REGISTRY NUMBER

COMMENTARY

113478-42-5

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

Reversibility
r=reversible
ir=irreversible
?=not specified

(S)-cis-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2

allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

3 entries

(S)-cis-N-methylcorydalmine + [reduced NADPH-hemoprotein reductase] + O2

muramine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: -
Products: -

(S)-cis-N-methylstylopine + [reduced NADPH-hemoprotein reductase] + O2

protopine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: -
Products: -

(S)-cis-N-methyltetrahydropalmitine + [reduced NADPH-hemoprotein reductase] + O2

muramine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: -
Products: -

(S)-cis-N-methyltetrahydrothalifendine + [reduced NADPH-hemoprotein reductase] + O2

thalictrisine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: -
Products: -

(S)-N-methylcanadine + NADPH + H+ + O2

allocryptopine + NADP+ + H2O

Corydalis vaginans

285317

Substrates: -
Products: -

(S)-cis-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2

allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: no activity without molecular oxygen
Products: -

(S)-cis-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2

allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: (R)-cis/trans-N-methyl-canadine is no substrate
Products: -

(S)-cis-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2

allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: hydroxylation in benzylisoquinoline metabolism
Products: -

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

(S)-cis-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2

allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

2 entries

(S)-cis-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2

allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: (R)-cis/trans-N-methyl-canadine is no substrate
Products: -

(S)-cis-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2

allocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O

Corydalis vaginans

285317

Substrates: hydroxylation in benzylisoquinoline metabolism
Products: -

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

cytochrome P450

Corydalis vaginans

285317

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

Ancymidol

Corydalis vaginans

285317

Corydalis vaginans

reversible by light

285317

cytochrome c

Corydalis vaginans

285317

ketoconazole

Corydalis vaginans

285317

Metyrapone

Corydalis vaginans

285317

Prochloraz

Corydalis vaginans

285317

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.0125

cis-N-methylcanadine

Corydalis vaginans

285317

0.0625

NADPH

Corydalis vaginans

285317

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SPECIFIC ACTIVITY [µmol/min/mg]

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

0.0255

Corydalis vaginans

285317

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

8.5

Corydalis vaginans

285317

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pH RANGE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

6.5 - 9.7

Corydalis vaginans

half-maximal activity at pH 6.5 and pH 9.7

285317

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Corydalis vaginans

285317

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TEMPERATURE RANGE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

10 - 45

Corydalis vaginans

half-maximal activity at 10°C and 45°C

285317

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only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks include all textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks + FRENDAco-occurrence of enzyme names and organism names (less precise)

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Corydalis vaginans

papaveraceae

285317

brenda

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only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

cell suspension culture

Corydalis vaginans

285317

brenda

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only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

microsome

Corydalis vaginans

membrane bound

285317

brenda

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Highest Expressing Human Cell Lines

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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).

L7X3S1 pBLAST

MSH_PAPSO

Papaver somniferum

526

59346

Swiss-Prot

Show Sequence

Secretory Pathway (Reliability: 4)

A0A396HB42 pBLAST

A0A396HB42_MEDTR

Medicago truncatula

132

15043

TrEMBL

Show Sequence

other Location (Reliability: 5)

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

285317

Rueffer, M.; Zenk, M.H.

Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans

Tetrahedron Lett.

5307-5310

1987

Corydalis vaginans

brenda

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EXTERNAL LINKS (specific for EC-Number 1.14.14.97)

ExplorEnz (official portal for IUBMB Enzyme Nomenclature)

Expasy Enzyme Nomenclature Database

KEGG

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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