CHEBI:4752 - (−)-echitovenine

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ChEBI Name (−)-echitovenine
ChEBI ASCII Name (-)-echitovenine
Definition An Aspidosperma alkaloid that is (5α,12β,19α)-2,3-didehydroaspidospermidine which is substituted by a methoxycarbonyl group at position 3 and by an acetoxy group at position 20.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H28N2O4
Net Charge 0
Average Mass 396.487
Monoisotopic Mass 396.20491
InChI InChI=1S/C23H28N2O4/c1-14(29-15(2)26)22-9-6-11-25-12-10-23(21(22)25)17-7-4-5-8-18(17)24-19(23)16(13-22)20(27)28-3/h4-5,7-8,14,21,24H,6,9-13H2,1-3H3/t14?,21-,22-,23-/m0/s1
SMILES [C@@]123[C@]4(N(CCC[C@]4(CC(=C1NC5=C2C=CC=C5)C(OC)=O)C(C)OC(=O)C)CC3)[H]
Metabolite of Species Details
Catharanthus trichophyllus (NCBI:txid319559) See: DOI
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.
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing (−)-echitovenine (CHEBI:4752) has role plant metabolite (CHEBI:76924)
(−)-echitovenine (CHEBI:4752) is a Aspidosperma alkaloid (CHEBI:142772)
(−)-echitovenine (CHEBI:4752) is a acetate ester (CHEBI:47622)
(−)-echitovenine (CHEBI:4752) is a enamine (CHEBI:47989)
(−)-echitovenine (CHEBI:4752) is a methyl ester (CHEBI:25248)
(−)-echitovenine (CHEBI:4752) is a organic heteropentacyclic compound (CHEBI:38164)
(−)-echitovenine (CHEBI:4752) is a tertiary amino compound (CHEBI:50996)
(−)-echitovenine (CHEBI:4752) is conjugate base of (−)-echitovenine(1+) (CHEBI:144384)
Incoming (−)-echitovenine(1+) (CHEBI:144384) is conjugate acid of (−)-echitovenine (CHEBI:4752)
methyl (5α,12β,19α)-20-acetoxy-2,3-didehydroaspidospermidine-3-carboxylate
methyl 20-(acetyloxy)-5α,12β,19α-2,3-didehydroaspidospermidine-3-carboxylate
methyl 20-acetoxy-2,3-didehydro-5α,12β,19α-aspidospermidine-3-carboxylate
Manual Xref Database
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Citation Waiting for Citations Type Source
21454651 PubMed citation Europe PMC
Last Modified
09 March 2020
General Comment
2019-09-24 Both enantiomeric forms of echitovenine occur naturally.