senecionine

Also known as aureine, Senecionin

Senecionine is a toxic pyrrolizidine alkaloid isolated from various botanical sources. It takes its name from the Senecio genus and is produced by many different plants in that genus, including Jacobaea vulgaris (Senecio jacobaea). It has also been isolated from several other plants, including Brachyglottis repanda, Emilia, Erechtites hieraciifolius, Petasites, Syneilesis, Crotalaria, Caltha leptosepala, and Castilleja.

Chemical data

Formula: C18H25NO5
Molecular weight: 335.4 g/mol
IUPAC name: (1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
SMILES: C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C
InChIKey: HKODIGSRFALUTA-JTLQZVBZSA-N
XLogP: 1.1
Polar surface area: 76.1 Å²
H-bond donors: 1
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

255 papers

via PubMed

Wikidata facts

Has part: carbon
Mass: 335.173273

Show 9 more facts

subject has role: poison
chemical formula: C₁₈H₂₅NO₅
Commons category: Senecionine
canonical SMILES: CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)C
isomeric SMILES: C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C
found in taxon: Emilia sonchifolia
has characteristic: bitterness
median lethal dose (LD50): 61
minimal lethal dose: 33

Sources (2)

via Wikidata · CC0

~8 min read

Encyclopedic overview

11 sections

Contents

Toxicity
Liver toxicity
DNA damage
Diagnosis
Other bioactivity
Treatment
Biosynthesis and chemistry
Metabolism and mechanism of action
Biology and society
See also
References

The compound is toxic and consumption can lead to liver damage, cancer, and pyrrolizidine alkaloidosis. Because of this, consumption of plants that produce it has resulted in poisonings, both in humans and in animals.

Excerpted from Wikipedia’s “senecionine” article, available under the CC BY-SA 4.0 licence.