CHEBI:141964 - vindolinine

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ChEBI Name vindolinine
ChEBI ID CHEBI:141964
Definition A monoterpenoid indole alkaloid with formula C21H24N2O2, isolated from several plant species.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
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Formula C21H24N2O2
Net Charge 0
Average Mass 336.428
Monoisotopic Mass 336.18378
InChI InChI=1S/C21H24N2O2/c1-13-19-8-5-10-23-11-9-20(18(19)23)14-6-3-4-7-16(14)22-21(13,20)15(12-19)17(24)25-2/h3-8,13,15,18,22H,9-12H2,1-2H3/t13-,15+,18+,19+,20-,21-/m1/s1
InChIKey JSLDLCGKZDUQSH-SBDPWIONSA-N
SMILES C12=CC=CC=C1N[C@@]34[C@@]25[C@@]6([C@](C[C@H]3C(=O)OC)(C=CCN6CC5)[C@@]4([H])C)[H]
Metabolite of Species Details
Melodinus tenuicaudatus (IPNI:80259-1) Found in bark (BTO:0001301). See: PubMed
Catharanthus lanceus (NCBI:txid1750993) Found in leaf (BTO:0000713). See: PubMed
Catharanthus trichophyllus (NCBI:txid319559) Found in root (BTO:0001188). See: PubMed
Catharanthus roseus (NCBI:txid4058) Found in leaf (BTO:0000713). See: PubMed
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 vindolinine (CHEBI:141964) has role plant metabolite (CHEBI:76924)
vindolinine (CHEBI:141964) is a methyl ester (CHEBI:25248)
vindolinine (CHEBI:141964) is a monoterpenoid indole alkaloid (CHEBI:65323)
vindolinine (CHEBI:141964) is a organic heteropentacyclic compound (CHEBI:38164)
vindolinine (CHEBI:141964) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
methyl (3β,5α,12β,19α,20R)-6,7-didehydro-2,20-cycloaspidospermidine-3-carboxylate
Synonyms Sources
(−)-vindolinine KNApSAcK
Vindolinin ChEBI
Manual Xref Database
C00024615 KNApSAcK
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Registry Numbers Types Sources
52849 Reaxys Registry Number Reaxys
5980-02-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15682277 PubMed citation Europe PMC
17265274 PubMed citation Europe PMC
24241871 PubMed citation Europe PMC
26854826 PubMed citation Europe PMC
4473533 PubMed citation Europe PMC
4530263 PubMed citation Europe PMC
5677682 PubMed citation Europe PMC
Last Modified
11 September 2018
General Comment
2018-09-11 Relevant article: Werner Kohl, Barbara Witte und Gerhard Höfle. Alkaloide aus Catharanthus roseus-Zellkulturen (1981). Z. Naturforsch. 86b, p 1153-1162.