Entry
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
BRITE hierarchy
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)
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
ec01110 Biosynthesis of secondary metabolites
Orthology
K20618 nepetalactol monooxygenase
Genes
APAN : 127251352 127251997
Taxonomy
Reference
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
Other DBs
LinkDB
All DBs