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

DBGET integrated database retrieval system