Structure via PubChem · Public domain (PubChem)
riddelliine
Sign in to saveAlso known as riddelline, riddeline, (15E)-12,18-Dihydroxy-13,19-didehydrosenecionan-11,16-dione
Riddelliine is a chemical compound classified as a pyrrolizidine alkaloid. It was first isolated from Senecio riddellii and is also found in a variety of plants including Jacobaea vulgaris, Senecio vulgaris, and others plants in the genus Senecio.
Chemical data
- Formula
- C18H23NO6
- Molecular weight
- 349.4 g/mol
- IUPAC name
- (1R,4Z,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
- SMILES
- C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O
- InChIKey
- SVCNNZDUGWLODJ-RAYFHMIRSA-N
- XLogP
- 0.2
- Polar surface area
- 96.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 349.152537456
Show 5 more facts
- chemical formula
- C₁₈H₂₃NO₆
- isomeric SMILES
- [H][C@]1(C(COC([C@@]2(O)CO)=O)=CC3)N3CC[C@H]1OC(/C(CC2=C)=C\C)=O
- found in taxon
- Crotalaria juncea
- canonical SMILES
- O=C1OC2CCN3CC=C(COC(=O)C(O)(C(=C)CC1=CC)CO)C32
- subject has role
- carcinogen
via Wikidata · CC0
~11 min read
Encyclopedic overview
13 sectionsContents
- Structure and Reactivity
- Synthesis
- Mechanism
- Toxicity
- Indications
- Adverse Effects
- Diseases
- Genotoxicity
- Carcinogenicity
- Effects on animals
- History
- See also
- References
Riddelliine is a chemical compound classified as a pyrrolizidine alkaloid. It was first isolated from Senecio riddellii and is also found in a variety of plants including Jacobaea vulgaris, Senecio vulgaris, and others plants in the genus Senecio.
Riddelliine can be found as a contaminant in foods such as meat, grains, seeds, milk, herbal tea, and honey.
Excerpted from Wikipedia’s “riddelliine” article, available under the CC BY-SA 4.0 licence.