KEGG   ORTHOLOGY: K20618
Entry
K20618                      KO                                     

Name
CYP76A26
Definition
nepetalactol monooxygenase [EC:1.14.14.161]
Pathway
ko00902  Monoterpenoid biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00902 Monoterpenoid biosynthesis
    K20618  CYP76A26; nepetalactol monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K20618  CYP76A26; nepetalactol monooxygenase
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
    1.14.14.161  nepetalactol monooxygenase
     K20618  CYP76A26; nepetalactol monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP76 family
   K20618  CYP76A26; nepetalactol monooxygenase
Other DBs
RN: R12182 R12231 R12253
Genes
SIND: 105174133
OEU: 111386126 111412687
AG: AHX24370(CYP76A26)
Reference
PMID:24594312 (CYP76A26)
  Authors
Salim V, Wiens B, Masada-Atsumi S, Yu F, De Luca V
  Title
7-deoxyloganetic acid synthase catalyzes a key 3 step oxidation to form 7-deoxyloganetic acid in Catharanthus roseus iridoid biosynthesis.
  Journal
Phytochemistry 101:23-31 (2014)
DOI:10.1016/j.phytochem.2014.02.009
  Sequence

KEGG   ENZYME: 1.14.14.161
Entry
EC 1.14.14.161              Enzyme                                 

Name
nepetalactol monooxygenase;
CYP76A26 (gene name);
iridoid oxidase (misleading)
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
(+)-cis,trans-nepetalactol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
Reaction(IUBMB)
(+)-cis,trans-nepetalactol + 3 [reduced NADPH---hemoprotein reductase] + 3 O2 = 7-deoxyloganetate + 3 [oxidized NADPH---hemoprotein reductase] + 4 H2O (overall reaction) [RN:R12230];
(1a) (+)-cis,trans-nepetalactol + [reduced NADPH---hemoprotein reductase] + O2 = 7-deoxyloganetic alcohol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12231];
(1b) 7-deoxyloganetic alcohol + [reduced NADPH---hemoprotein reductase] + O2 = iridotrial + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R12253];
(1c) iridotrial + [reduced NADPH---hemoprotein reductase] + O2 = 7-deoxyloganetate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12182]
Reaction(KEGG)
R12182 R12230 R12231 R12253;
(other) R12181
Substrate
(+)-cis,trans-nepetalactol [CPD:C09804];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
7-deoxyloganetic alcohol [CPD:C22014];
iridotrial [CPD:C06070]
Product
7-deoxyloganetate [CPD:C20789];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
7-deoxyloganetic alcohol [CPD:C22014];
iridotrial [CPD:C06070]
Comment
The enzyme, characterized from the plant Catharanthus roseus, is a cytochrome P-450 (heme thiolate) protein. It catalyses three successive reactions in the pathway leading to biosynthesis of monoterpenoid indole alkaloids.
History
EC 1.14.14.161 created 2018
Pathway
ec00902  Monoterpenoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K20618  nepetalactol monooxygenase
Genes
SIND: 105174133
OEU: 111386126 111412687
Reference
1  [PMID:24710322]
  Authors
Miettinen K, Dong L, Navrot N, Schneider T, Burlat V, Pollier J, Woittiez L, van der Krol S, Lugan R, Ilc T, Verpoorte R, Oksman-Caldentey KM, Martinoia E, Bouwmeester H, Goossens A, Memelink J, Werck-Reichhart D.
  Title
The seco-iridoid pathway from Catharanthus roseus.
  Journal
Nat Commun 5:3606 (2014)
DOI:10.1038/ncomms4606
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.161
IUBMB Enzyme Nomenclature: 1.14.14.161
ExPASy - ENZYME nomenclature database: 1.14.14.161
BRENDA, the Enzyme Database: 1.14.14.161

KEGG   REACTION: R12253
Entry
R12253                      Reaction                               

Name
7-deoxyloganetic alcohol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
Definition
7-Deoxyloganetic alcohol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Iridotrial + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Equation
Comment
the second step of three-step reaction (see R12230, R12231+R12253+R12182)
Enzyme
Pathway
rn00902  Monoterpenoid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Orthology
K20618  nepetalactol monooxygenase [EC:1.14.14.161]

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