CHEBI:141967 - voachalotine

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ChEBI Name voachalotine
ChEBI ID CHEBI:141967
Definition A monoterpenoid indole alkaloid with formula C22H26N2O3, isolated from several Tabernaemontana species.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information
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Formula C22H26N2O3
Net Charge 0
Average Mass 366.454
Monoisotopic Mass 366.19434
InChI InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4-/t16-,18-,19-,22+/m0/s1
InChIKey IWEYXWIPVZEVPT-VQVRLUHXSA-N
SMILES [C@]1([C@]2(N3[C@@](C[C@]1(/C(/C3)=C\C)[H])(C4=C(C2)C5=C(N4C)C=CC=C5)[H])[H])(C(OC)=O)CO
Metabolite of Species Details
Tabernaemontana australis (IPNI:315554-2) See: PubMed
Ervatamia officinalis (IPNI:78954-1) See: PubMed
Ochrosia acuminata (IPNI:80487-1) Found in root (BTO:0001188). See: PubMed
Tabernaemontana catharinensis (NCBI:txid403124) Found in aerial part (BTO:0001658). See: PubMed
Tabernaemontana catharinensis (NCBI:txid403124) Found in root (BTO:0001188). See: PubMed
Neisosperma acuminatum (NCBI:txid453904) Found in root (BTO:0001188). See: PubMed
Tabernaemontana buchtieni (NCBI:txid52860) Found in bark (BTO:0001301). Isolated from stem bark. See: Azoug, M., Loukaci, A., Richard, B., Nuzillard, J.M., Moreti, C., Hanrot, M.Z. and Olivier, L.L.M. (1995) Alkaloids from stem bark and leaves of Peschiera buchtieni. Phytochemistry, 39(8), 1223-1228.
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): 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 voachalotine (CHEBI:141967) is a methyl ester (CHEBI:25248)
voachalotine (CHEBI:141967) is a monoterpenoid indole alkaloid (CHEBI:65323)
voachalotine (CHEBI:141967) is a organic heteropentacyclic compound (CHEBI:38164)
voachalotine (CHEBI:141967) is a primary alcohol (CHEBI:15734)
voachalotine (CHEBI:141967) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
methyl (19E)-16-(hydroxymethyl)-1-methylsarpagan-17-oate
Synonyms Sources
voachalotin ChEBI
voachalotine ChemIDplus
Manual Xref Database
C00040643 KNApSAcK
View more database links
Registry Numbers Types Sources
664-25-5 CAS Registry Number KNApSAcK
664-25-5 CAS Registry Number ChemIDplus
6748787 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15497947 PubMed citation Europe PMC
15911323 PubMed citation Europe PMC
17253850 PubMed citation Europe PMC
21892126 PubMed citation Europe PMC
23983637 PubMed citation Europe PMC
Last Modified
01 November 2018