CHEBI:70507 - (−)-vincadifformine

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ChEBI Name (−)-vincadifformine
ChEBI ID CHEBI:70507
ChEBI ASCII Name (-)-vincadifformine
Definition An aspidosperma alkaloid that is (5α,12β,19α)-2,3-didehydroaspidospermidine which is substituted at position 3 by a methoxycarbonyl group. A natural product found in several species in the Apocynaceae (dogbane) family, including Alstonia spatulata.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H26N2O2
Net Charge 0
Average Mass 338.444
Monoisotopic Mass 338.19943
InChI InChI=1S/C21H26N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-5,7-8,19,22H,3,6,9-13H2,1-2H3/t19-,20-,21-/m0/s1
InChIKey GIGFIWJRTMBSRP-ACRUOGEOSA-N
SMILES C=1(C[C@]2([C@@]3(N(CCC2)CC[C@]43C5=C(NC41)C=CC=C5)[H])CC)C(=O)OC
Metabolite of Species Details
Alstonia sp.tulata (IPNI:76595-1) Found in leaf (BTO:0000713). Extraction of leaves with concentrated EtOH with dilute acids 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.
antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-vincadifformine (CHEBI:70507) has role antiplasmodial drug (CHEBI:64915)
(−)-vincadifformine (CHEBI:70507) has role plant metabolite (CHEBI:76924)
(−)-vincadifformine (CHEBI:70507) is a Aspidosperma alkaloid (CHEBI:142772)
(−)-vincadifformine (CHEBI:70507) is a methyl ester (CHEBI:25248)
(−)-vincadifformine (CHEBI:70507) is a organic heteropentacyclic compound (CHEBI:38164)
(−)-vincadifformine (CHEBI:70507) is a organonitrogen heterocyclic compound (CHEBI:38101)
(−)-vincadifformine (CHEBI:70507) is a secondary amino compound (CHEBI:50995)
(−)-vincadifformine (CHEBI:70507) is a tertiary amino compound (CHEBI:50996)
(−)-vincadifformine (CHEBI:70507) is conjugate base of (−)-vincadifformine(1+) (CHEBI:142771)
(−)-vincadifformine (CHEBI:70507) is enantiomer of (+)-vincadifformine (CHEBI:142834)
Incoming (−)-vincadifformine(1+) (CHEBI:142771) is conjugate acid of (−)-vincadifformine (CHEBI:70507)
(+)-vincadifformine (CHEBI:142834) is enantiomer of (−)-vincadifformine (CHEBI:70507)
IUPAC Name
methyl (5α,12β,19α)-2,3-didehydroaspidospermidine-3-carboxylate
Synonyms Sources
(5α,12β,19α)-2,3-didehydroaspidospermidine-3-carboxylic acid methyl ester ChEBI
6,7-dihydrotabersonine ChEBI
aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methylester, (5alpha,12beta,19alpha)- ChEBI
methyl (5S,12R,19S)-2,3-didehydroaspidospermidine-3-carboxylate ChEBI
vincadifformine ChEBI
Manual Xref Database
C00024463 KNApSAcK
View more database links
Registry Number Type Source
3247-10-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
13900664 PubMed citation Europe PMC
13935801 PubMed citation Europe PMC
13943964 PubMed citation Europe PMC
21043460 PubMed citation Europe PMC
21753848 PubMed citation Europe PMC
23971538 PubMed citation Europe PMC
25522533 PubMed citation Europe PMC
27936683 PubMed citation Europe PMC
29131648 PubMed citation Europe PMC
Last Modified
01 January 2019
General Comment
2018-12-11 For details on antiplasmodial activity, see Indonesian J. Biotechnol., 2006, 11(1), 878-883.