Information on EC 1.14.19.50 - noroxomaritidine synthase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.14.19.50
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RECOMMENDED NAME
GeneOntology No.
noroxomaritidine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2 = (4aS,10bR)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(2)
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-
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4'-O-methylnorbelladine + [reduced NADPH—hemoprotein reductase] + O2 = (4aR,10bS)-noroxomaritidine + [oxidized NADPH—hemoprotein reductase] + 2 H2O
show the reaction diagram
(1)
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Amaryllidacea alkaloids biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
4'-O-methylnorbelladine,NADPH—hemoprotein reductase:oxygen oxidoreductase (noroxomaritidine-forming)
A P-450 (heme-thiolate) enzyme. The enzyme, characterized from Narcissus pseudonarcissus (daffodil), forms the two enantiomers of the Amaryllidacea alkaloid noroxomaritidine by catalysing intramolecular oxidative para-para' phenol coupling. The oxidation involves molecular oxygen without its incorporation into the product.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Narcissus sp. aff. pseudonarcissus
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UniProt
Manually annotated by BRENDA team
Narcissus sp. aff. pseudonarcissus MK-2014
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UniProt
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2) 4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
(4aS,10bR)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(R)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(S)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
4'-O-methyl-N-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
(4aR,10bS)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
Narcissus sp. aff. pseudonarcissus
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formation of the para-ortho' phenol coupled product, N-demethylnarwedine, at less than 1% of the total product
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?
additional information
?
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
substrate inhibition
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4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
substrate inhibition
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.659
(R)-Coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.637
(S)-Coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.00328
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
-
0.00113
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.035
(R)-Coclaurine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
0.022
(S)-Coclaurine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
0.041
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
-
0.25
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.053
(R)-Coclaurine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
10452
0.035
(S)-Coclaurine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
5082
12.37
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
212598
216.7
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
A0A140IL90
pH 8.0, 30°C
212337
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.174
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
-
0.064
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.19.50)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)