CHEBI:137485 - (3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine
ChEBI ID CHEBI:137485
ChEBI ASCII Name (3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine
Definition A monoterpenoid indole alkaloid that is a reactive intermediate in the biosynthesis of vindoline by Catharanthus roseus.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H26N2O4
Net Charge 0
Average Mass 382.454
Monoisotopic Mass 382.18926
InChI InChI=1S/C22H26N2O4/c1-4-20-8-5-10-24-11-9-21(18(20)24)15-7-6-14(27-2)12-16(15)23-17(21)22(26,13-20)19(25)28-3/h5-8,12,18,26H,4,9-11,13H2,1-3H3/t18-,20-,21-,22+/m0/s1
InChIKey ADHQBWGHPFFYKI-JKLQHZFJSA-N
SMILES [C@@]123C(=NC4=C1C=CC(=C4)OC)[C@](C[C@]5([C@@]2(N(CC=C5)CC3)[H])CC)(C(=O)OC)O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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
ChEBI Ontology
Outgoing (3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) has functional parent 16-hydroxytabersonine (CHEBI:17699)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) has role plant metabolite (CHEBI:76924)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) is a aromatic ether (CHEBI:35618)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) is a methyl ester (CHEBI:25248)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) is a monoterpenoid indole alkaloid (CHEBI:65323)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) is a organic heteropentacyclic compound (CHEBI:38164)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) is a tertiary alcohol (CHEBI:26878)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) is a tertiary amino compound (CHEBI:50996)
(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485) is conjugate base of (3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersoninium (CHEBI:136640)
Incoming (3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersoninium (CHEBI:136640) is conjugate acid of (3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine (CHEBI:137485)
IUPAC Name
methyl (3β,5α,12β,19α)-3-hydroxy-16-methoxy-1,2,6,7-tetradehydroaspidospermidine-3-carboxylate
Manual Xref Database
CPD-19892 MetaCyc
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Registry Number Type Source
28120142 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
25918424 PubMed citation Europe PMC
Last Modified
21 June 2017