InChI=1S/C16H17NO3/c1-20-14-8-12-10(6-13(14)19)9-17-5-4-16(12)3-2-11(18)7-15(16)17/h2-3,6,8,15,19H,4-5,7,9H2,1H3/t15-,16-/m0/s1 |
VEXDOCFQMVMPHJ-HOTGVXAUSA-N |
C1(=C(C=C2C(=C1)[C@@]34[C@@](N(C2)CC3)(CC(C=C4)=O)[H])O)OC |
|
Galanthus elwesii
(NCBI:txid82232)
|
See:
PubMed
|
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
|
|
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
|
|
View more via ChEBI Ontology
Outgoing
|
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
has role
plant metabolite
(CHEBI:76924)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
aromatic ether
(CHEBI:35618)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
bridged compound
(CHEBI:35990)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
cyclic ketone
(CHEBI:3992)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
enone
(CHEBI:51689)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
isoquinoline alkaloid
(CHEBI:24921)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
organic heterotetracyclic compound
(CHEBI:38163)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
phenols
(CHEBI:33853)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is a
tertiary amino compound
(CHEBI:50996)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is conjugate base of
(4aS,10bR)-noroxomaritidine(1+)
(CHEBI:133995)
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
is enantiomer of
(4aR,10bS)-noroxomaritidine
(CHEBI:136560)
|
|
Incoming
|
(4aS,10bR)-noroxomaritidine(1+)
(CHEBI:133995)
is conjugate acid of
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
(4aR,10bS)-noroxomaritidine
(CHEBI:136560)
is enantiomer of
(4aS,10bR)-noroxomaritidine
(CHEBI:136557)
|
(4aS,10bR)-8-hydroxy-9-methoxy-4,4a-dihydro-3H,6H-5,10b-ethanophenanthridin-3-one
|
1545884
|
Reaxys Registry Number
|
Reaxys
|
21385538
|
Reaxys Registry Number
|
Reaxys
|
Kilgore MB, Augustin MM, May GD, Crow JA, Kutchan TM (2016) CYP96T1 of Narcissus sp. aff. pseudonarcissus Catalyzes Formation of the Para-Para' C-C Phenol Couple in the Amaryllidaceae Alkaloids. Frontiers in plant science 7, 225 [PubMed:26941773] [show Abstract] The Amaryllidaceae alkaloids are a family of amino acid derived alkaloids with many biological activities; examples include haemanthamine, haemanthidine, galanthamine, lycorine, and maritidine. Central to the biosynthesis of the majority of these alkaloids is a C-C phenol-coupling reaction that can have para-para', para-ortho', or ortho-para' regiospecificity. Through comparative transcriptomics of Narcissus sp. aff. pseudonarcissus, Galanthus sp., and Galanthus elwesii we have identified a para-para' C-C phenol coupling cytochrome P450, CYP96T1, capable of forming the products (10bR,4aS)-noroxomaritidine and (10bS,4aR)-noroxomaritidine from 4'-O-methylnorbelladine. CYP96T1 was also shown to catalyzed formation of the para-ortho' phenol coupled product, N-demethylnarwedine, as less than 1% of the total product. CYP96T1 co-expresses with the previously characterized norbelladine 4'-O-methyltransferase. The discovery of CYP96T1 is of special interest because it catalyzes the first major branch in Amaryllidaceae alkaloid biosynthesis. CYP96T1 is also the first phenol-coupling enzyme characterized from a monocot. |
|