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Information on EC 1.14.14.167 - (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase and Organism(s) Papaver somniferum and UniProt Accession I3V6B7

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IUBMB Comments
This cytochrome P-450 (heme-thiolate) enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
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This record set is specific for:
Papaver somniferum
UNIPROT: I3V6B7
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The taxonomic range for the selected organisms is: Papaver somniferum
The expected taxonomic range for this enzyme is: Papaver somniferum
Synonyms
1-hydroxy-13-O-acetyl-N-methylcanadine 8-hydroxylase, CYP82X1, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1-hydroxy-13-O-acetyl-N-methylcanadine 8-hydroxylase
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CYP82X1
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-
-
-
SYSTEMATIC NAME
IUBMB Comments
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
This cytochrome P-450 (heme-thiolate) enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2
(13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(S)-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
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-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2
(13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
heme-thiolate enzyme
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0049
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine
pH 7.5, 30°C
0.0106
(S)-1-hydroxy-N-methylcanadine
pH 7.5, 30°C
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
C82X1_PAPSO
540
1
61207
Swiss-Prot
Secretory Pathway (Reliability: 2)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae. Reconstitution of the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
reconstitute of the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Dang, T.; Chen, X.; Facchini, P.
Acetylation serves as a protective group in noscapine biosynthesis in opium poppy
Nat. Chem. Biol.
11
104-106
2015
Papaver somniferum (I3V6B7)
Manually annotated by BRENDA team
Li, Y.; Smolke, C.
Engineering biosynthesis of the anticancer alkaloid noscapine in yeast
Nat. Commun.
7
12137
2016
Papaver somniferum (I3V6B7)
Manually annotated by BRENDA team
Li, Y.; Li, S.; Thodey, K.; Trenchard, I.; Cravens, A.; Smolke, C.
Complete biosynthesis of noscapine and halogenated alkaloids in yeast
Proc. Natl. Acad. Sci. USA
115
E3922-E3931
2018
Papaver somniferum (I3V6B7)
Manually annotated by BRENDA team