EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

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

ChEBI IDCHEBI:137485
ChEBI Name(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine
Stars
ASCII Name(3R)-1,2-didehydro-3-hydroxy-16-methoxy-2,3-dihydrotabersonine
DefinitionA monoterpenoid indole alkaloid that is a reactive intermediate in the biosynthesis of vindoline by Catharanthus roseus.
Last Modified21 June 2017
SubmitterSteve
DownloadsMolfile
FormulaC22H26N2O4
Net Charge0
Average Mass382.460
Monoisotopic Mass382.18926
SMILES[H][C@]12N3CC=C[C@@]1(CC)C[C@](O)(C(=O)OC)C1=Nc4cc(OC)ccc4[C@@]12CC3
InChIInChI=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
InChIKeyADHQBWGHPFFYKI-JKLQHZFJSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
(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 Relation(s)
(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 XrefsDatabases
CPD-19892MetaCyc
Registry NumbersSources
Reaxys:28120142Reaxys
Citations