Structure via PubChem · Public domain (PubChem)
cerberin
Sign in to saveAlso known as 3beta-O-(L-2'-O-acetylthevetosyl)-14beta-hydroxy-5beta-card-20(22)-enolide, 2'-Acetylneriifolin
Cerberin is a type of cardiac glycoside found in the seeds of trees in the genus Cerbera, including the suicide tree (Cerbera odollam) and the sea mango (Cerbera manghas). As a cardiac glycoside, cerberin disrupts the function of the heart by blocking its sodium and potassium ATPase. Cerberin can be used as a treatment for heart failure and arrhythmia.
Chemical data
- Formula
- C32H48O9
- Molecular weight
- 576.7 g/mol
- IUPAC name
- [(2R,3S,4R,5S,6S)-5-hydroxy-2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-6-methyloxan-3-yl] acetate
- SMILES
- C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O
- InChIKey
- UYQMTWMXBKEHJQ-IVHDSYOHSA-N
- XLogP
- 2.7
- Polar surface area
- 121 Ų
- H-bond donors
- 2
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 576.33
Show 4 more facts
- canonical SMILES
- CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O
- chemical formula
- C₃₂H₄₈O₉
- isomeric SMILES
- C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O
- found in taxon
- Thevetia
Sources (2)
via Wikidata · CC0
~10 min read
Encyclopedic overview
14 sectionsContents
- Structure and properties
- Structure
- Physical properties
- Toxicity
- Symptoms
- Poisonings
- Mechanism of action
- Na<sup>+</sup>/K<sup>+</sup>-ATPase pump
- Na<sup>+</sup>/Ca<sup>2+</sup>-exchanger
- Metabolism
- Efficacy
- Therapeutic uses
- Further reading
- References
Cerberin is a type of cardiac glycoside found in the seeds of trees in the genus Cerbera, including the suicide tree (Cerbera odollam) and the sea mango (Cerbera manghas). As a cardiac glycoside, cerberin disrupts the function of the heart by blocking its sodium and potassium ATPase. Cerberin can be used as a treatment for heart failure and arrhythmia.
Overconsumption of cerberin results in poisoning. Symptoms include nausea, vomiting, and bradycardia, often leading to death. Cerberin-containing plants such as Cerbera odollam have historically been used for suicide and homicide in their native regions due to their high toxicity.
Excerpted from Wikipedia’s “cerberin” article, available under the CC BY-SA 4.0 licence.