Information on EC 1.14.21.5 - (S)-canadine synthase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.14.21.5
-
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RECOMMENDED NAME
GeneOntology No.
(S)-canadine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-tetrahydrocolumbamine + NADPH + H+ + O2 = (S)-canadine + NADP+ + 2 H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
berberine biosynthesis
-
-
Biosynthesis of secondary metabolites
-
-
Isoquinoline alkaloid biosynthesis
-
-
noscapine biosynthesis
-
-
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SYSTEMATIC NAME
IUBMB Comments
(S)-tetrahydrocolumbamine,NADPH:oxygen oxidoreductase (methylenedioxy-bridge-forming)
A heme-thiolate enzyme (P-450) catalysing an oxidative reaction that does not incorporate oxygen into the product. Oxidation of the methoxyphenol group of the alkaloid tetrahydrocolumbamine results in the formation of the methylenedioxy bridge of canadine.
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CAS REGISTRY NUMBER
COMMENTARY hide
114308-22-4
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Berberis crataegina
-
-
-
Manually annotated by BRENDA team
Berberis henryana
-
-
-
Manually annotated by BRENDA team
Berberis taliensis
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Thalictrum flavum ssp. glaucum
-
-
-
Manually annotated by BRENDA team
Thalictrum glabrum
-
-
-
Manually annotated by BRENDA team
Thalictrum glaucum
-
-
-
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
virus-induced gene silencing of CYP719A21 causes a significant increase in (S)-tetrahydrocolumbamine accumulation and a corresponding decrease in the levels of putative downstream intermediates and noscapine
physiological function
CYP719A13 can be involved in both sanguinarine and berberine formation in Argemone mexicana
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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
(S)-tetrahydrocolumbamine + NADH + O2
?
show the reaction diagram
(S)-tetrahydrocolumbamine + NADPH + H+ + O2
(S)-canadine + NADP+ + H2O
show the reaction diagram
(S)-tetrahydrocolumbamine + NADPH + O2
(S)-canadine + NADP+ + H2O
show the reaction diagram
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-tetrahydrocolumbamine + NADPH + H+ + O2
(S)-canadine + NADP+ + H2O
show the reaction diagram
-
strict substrate specificity and high affinity for (S)-tetrahydrocolumbamine
-
-
?
(S)-tetrahydrocolumbamine + NADPH + O2
(S)-canadine + NADP+ + H2O
show the reaction diagram
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome c
-
microsomal-bound enzyme
juglone
-
microsomal-bound enzyme
ketoconazole
-
microsomal-bound enzyme
menadione
-
microsomal-bound enzyme
Metyrapone
-
microsomal-bound enzyme
Plumbagin
-
microsomal-bound enzyme
Prochloraz
-
microsomal-bound enzyme
Propiconazole
-
microsomal-bound enzyme
Tetcyclacis
-
microsomal-bound enzyme
Triadimefone
-
microsomal-bound enzyme
tropolone
-
microsomal-bound enzyme
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00463 - 2.7
(S)-tetrahydrocolumbamine
0.033
NADPH
-
canadine synthase in complex with a cytochrome P-450 reductase
0.0115
tetrahydrocolumbamine
-
canadine synthase in complex with a cytochrome P-450 reductase
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5
-
canadine synthase in complex with a cytochrome P-450 reductase
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10
half optimal activity at pH 6.5 and pH 9
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
canadine synthase in complex with a cytochrome P-450 reductase
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57450
calculated from cDNA
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae strain YPL 154C:Pep4
-
expressed in Spodoptera frugiperda Sf9 cells
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.21.5)
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)