CHEBI:141966 - voacangine

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ChEBI Name voacangine
ChEBI ID CHEBI:141966
Definition A monoterpenoid indole alkaloid with formula C22H28N2O3, isolated from several plant species.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
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Formula C22H28N2O3
Net Charge 0
Average Mass 368.470
Monoisotopic Mass 368.20999
InChI InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14+,20+,22-/m1/s1
InChIKey MMAYTCMMKJYIAM-PHKAQXKASA-N
SMILES CC[C@H]1C[C@@]2(C[C@]3(C4=C(CCN(C2)[C@@]13[H])C=5C=C(C=CC5N4)OC)C(=O)OC)[H]
Metabolite of Species Details
Ervatamia pandacaqui (IPNI:78961-1) Found in leaf (BTO:0000713). See: PubMed
Ervatamia yunnanensis (IPNI:78987-1) Found in stem (BTO:0001300). See: PubMed
Voacanga schweinfurthii (NCBI:txid1239737) See: PubMed
Voacanga africana (NCBI:txid141630) Found in bark (BTO:0001301). See: PubMed
Voacanga africana (NCBI:txid141630) Found in bark (BTO:0001301). See: PubMed
Tabernaemontana catharinensis (NCBI:txid403124) See: Pereira, C.G., Carvalho, J.E. and Meireles, M.A.A. Anticancer activity of Tabernaemontana catharinensis extract obtained by supercritical fluid extraction (2006). Rev. Bras. Pl. Med., Botucatu, 8(4), p 144–149.
Tabernaemontana divaricata (NCBI:txid52861) Found in flower (BTO:0000469). See: PubMed
Tabernaemontana arborea (NCBI:txid681494) Found in bark (BTO:0001301). See: PubMed
Trachelospermum jasminoides (NCBI:txid69389) Found in leaf (BTO:0000713). See: PubMed
Tabernaemontana alba (NCBI:txid761051) Found in bark (BTO:0001301). See: PubMed
Tabernaemontana psorocarpa (NCBI:txid761091) Found in bark (BTO:0001301). 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 )
Application(s): angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing voacangine (CHEBI:141966) has role angiogenesis inhibitor (CHEBI:48422)
voacangine (CHEBI:141966) has role antineoplastic agent (CHEBI:35610)
voacangine (CHEBI:141966) has role plant metabolite (CHEBI:76924)
voacangine (CHEBI:141966) is a methyl ester (CHEBI:25248)
voacangine (CHEBI:141966) is a monoterpenoid indole alkaloid (CHEBI:65323)
voacangine (CHEBI:141966) is a organic heteropentacyclic compound (CHEBI:38164)
voacangine (CHEBI:141966) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
methyl 12-methoxyibogamine-18-carboxylate
Synonyms Sources
(−)-voacangine KNApSAcK
12-methoxyibogamine-18-carboxylic acid methyl ester ChEBI
carbomethoxyibogaine KNApSAcK
Manual Xrefs Databases
C00025223 KNApSAcK
Voacangine Wikipedia
View more database links
Registry Numbers Types Sources
510-22-5 CAS Registry Number ChemIDplus
510-22-5 CAS Registry Number KNApSAcK
55361 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14254313 PubMed citation Europe PMC
17268963 PubMed citation Europe PMC
17405098 PubMed citation Europe PMC
19647051 PubMed citation Europe PMC
22155252 PubMed citation Europe PMC
23569415 PubMed citation Europe PMC
24484240 PubMed citation Europe PMC
26140390 PubMed citation Europe PMC
27448833 PubMed citation Europe PMC
29728039 PubMed citation Europe PMC
29883785 PubMed citation Europe PMC
Last Modified
20 September 2018