CHEBI:142075 - tabernaemontanine

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ChEBI Name tabernaemontanine
ChEBI ID CHEBI:142075
Definition A monoterpenoid indole alkaloid with formula C21H26N2O3, isolated from several species of Tabernaemontana.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
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Formula C21H26N2O3
Net Charge 0
Average Mass 354.444
Monoisotopic Mass 354.19434
InChI InChI=1S/C21H26N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h5-8,12,14,17,19,22H,4,9-11H2,1-3H3/t12-,14+,17+,19+/m1/s1
InChIKey FFVRRQMGGGTQRH-DTPILHQWSA-N
SMILES CC[C@@H]1CN(C)[C@]2(CC=3C4=CC=CC=C4NC3C(C[C@@]1([C@@]2(C(=O)OC)[H])[H])=O)[H]
Metabolite of Species Details
Ervatamia yunnanensis (IPNI:78987-1) Found in aerial part (BTO:0001658). See: Yang, Y., Jinming, G., and Jikai, L. ' The constituents of Ervatamia yunnanensis' (1999). Acta Botanica Yunnanica. vol 21(3), p 399-405.
Tabernaemontana coronaria (IPNI:82068-1) Found in bark (BTO:0001301). See: PubMed
Tabernaemontana corymbosa (NCBI:txid1679252) Found in leaf (BTO:0000713). See: PubMed
Tabernaemontana divaricata (NCBI:txid52861) See: PubMed
Tabernaemontana elegans (NCBI:txid761068) Found in root (BTO:0001188). See: PubMed
Tabernaemontana elegans (NCBI:txid761068) 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.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tabernaemontanine (CHEBI:142075) has role antineoplastic agent (CHEBI:35610)
tabernaemontanine (CHEBI:142075) has role apoptosis inducer (CHEBI:68495)
tabernaemontanine (CHEBI:142075) has role plant metabolite (CHEBI:76924)
tabernaemontanine (CHEBI:142075) is a alkaloid ester (CHEBI:38481)
tabernaemontanine (CHEBI:142075) is a methyl ester (CHEBI:25248)
tabernaemontanine (CHEBI:142075) is a monoterpenoid indole alkaloid (CHEBI:65323)
tabernaemontanine (CHEBI:142075) is a organic heterotetracyclic compound (CHEBI:38163)
tabernaemontanine (CHEBI:142075) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
methyl (20β)-3-oxo-19,20-dihydrovobasan-17-oate
Synonyms Sources
(−)-tabernaemontanine KNApSAcK
(−)-tabernemontanine KNApSAcK
20-epidregamine KNApSAcK
tabernaemontanin KNApSAcK
tabernemontanine ChEBI
Manual Xref Database
C00026055 KNApSAcK
View more database links
Registry Numbers Types Sources
2134-98-7 CAS Registry Number KNApSAcK
32846872 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
13740864 PubMed citation Europe PMC
17253850 PubMed citation Europe PMC
19525111 PubMed citation Europe PMC
26169128 PubMed citation Europe PMC
28189906 PubMed citation Europe PMC
28423921 PubMed citation Europe PMC
29758521 PubMed citation Europe PMC
Last Modified
06 March 2020