KEGG   ORTHOLOGY: K22096
Entry
K22096            Tight     KO                                     
Symbol
CYP82X1
Name
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase [EC:1.14.14.167]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00946  Noscapine biosynthesis, (S)-reticuline => noscapine
Reaction
R11690  (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K22096  CYP82X1; (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K22096  CYP82X1; (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
Enzymes [BR:ko01000]
 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
    1.14.14.167  (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
     K22096  CYP82X1; (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP82 family
   K22096  CYP82X1; (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
Genes
PSOM: 113322295
AG: AFB74614(CYP82X1)
Reference
PMID:22653730
  Authors
Winzer T, Gazda V, He Z, Kaminski F, Kern M, Larson TR, Li Y, Meade F, Teodor R, Vaistij FE, Walker C, Bowser TA, Graham IA
  Title
A Papaver somniferum 10-gene cluster for synthesis of the anticancer alkaloid noscapine.
  Journal
Science 336:1704-8 (2012)
DOI:10.1126/science.1220757
  Sequence
[ag:AFB74614]
Reference
PMID:25485687
  Authors
Dang TT, Chen X, Facchini PJ
  Title
Acetylation serves as a protective group in noscapine biosynthesis in opium poppy.
  Journal
Nat Chem Biol 11:104-6 (2015)
DOI:10.1038/nchembio.1717
LinkDB

KEGG   ENZYME: 1.14.14.167
Entry
EC 1.14.14.167              Enzyme                                 
Name
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase;
CYP82X1 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
(13S,14R)-13-O-acetyl-1-hydroxy-cis-N-methylcanadine 8-hydroxylase,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
Reaction(IUBMB)
(13S,14R)-13-O-acetyl-1-hydroxy-cis-N-methylcanadine + [reduced NADPH---hemoprotein reductase] + O2 = (13S,14R)-13-O-acetyl-1,8-dihydroxy-cis-N-methylcanadine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11690]
Reaction(KEGG)
R11690
Substrate
(13S,14R)-13-O-acetyl-1-hydroxy-cis-N-methylcanadine [CPD:C21588];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(13S,14R)-13-O-acetyl-1,8-dihydroxy-cis-N-methylcanadine [CPD:C21589];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
This cytochrome P-450 (heme-thiolate) enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
History
EC 1.14.14.167 created 2018
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22096  (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
Genes
PSOM: 113322295
Reference
1  [PMID:25485687]
  Authors
Dang TT, Chen X, Facchini PJ
  Title
Acetylation serves as a protective group in noscapine biosynthesis in opium poppy.
  Journal
Nat Chem Biol 11:104-6 (2015)
DOI:10.1038/nchembio.1717
Reference
2  [PMID:27378283]
  Authors
Li Y, Smolke CD
  Title
Engineering biosynthesis of the anticancer alkaloid noscapine in yeast.
  Journal
Nat Commun 7:12137 (2016)
DOI:10.1038/ncomms12137
Reference
3  [PMID:29610307]
  Authors
Li Y, Li S, Thodey K, Trenchard I, Cravens A, Smolke CD
  Title
Complete biosynthesis of noscapine and halogenated alkaloids in yeast.
  Journal
Proc Natl Acad Sci U S A 115:E3922-E3931 (2018)
DOI:10.1073/pnas.1721469115
  Sequence
[ag:AFB74614]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.167
IUBMB Enzyme Nomenclature: 1.14.14.167
ExPASy - ENZYME nomenclature database: 1.14.14.167
BRENDA, the Enzyme Database: 1.14.14.167
LinkDB

KEGG   REACTION: R11690
Entry
R11690                      Reaction                               
Name
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
Definition
(13S,14R)-13-O-Acetyl-1-hydroxy-cis-N-methylcanadine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (13S,14R)-13-O-Acetyl-1,8-dihydroxy-cis-N-methylcanadine + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C21588 + C03024 + C00007 <=> C21589 + C03161 + C00001
Comment
1-hydroxy-13-O-acetyl-N-methylcanadine 8-hydroxylase
Reaction class
RC03497  C21588_C21589
Enzyme
1.14.14.167
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00946  Noscapine biosynthesis, (S)-reticuline => noscapine
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  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
    1.14.14.167
     R11690  (13S,14R)-13-O-Acetyl-1-hydroxy-cis-N-methylcanadine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (13S,14R)-13-O-Acetyl-1,8-dihydroxy-cis-N-methylcanadine + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K22096  (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase [EC:1.14.14.167]
LinkDB

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