cereulide

Cereulide is a heat-stable toxin produced by some strains of Bacillus cereus, B. megaterium and related species. It is a potent cytotoxin that destroys mitochondria. It causes nausea and vomiting.

Chemical data

Formula: C57H96N6O18
Molecular weight: 1153.4 g/mol
IUPAC name: (3R,6R,9S,12S,15R,18R,21S,24S,27R,30R,33S,36S)-3,15,27-trimethyl-6,18,30-tris(2-methylpropyl)-9,12,21,24,33,36-hexa(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone

via PubChem

Wikidata facts

Mass: 1152.678110232
Image: Cereulide.svg

Show 4 more facts

isomeric SMILES: O=C1N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H]1C(C)C)C)CC(C)C)C(C)C)C(C)C)C)CC(C)C)C(C)C)C(C)C)C)CC(C)C)C(C)C
chemical formula: C₅₇H₉₆N₆O₁₈
found in taxon: Bacillus cereus
canonical SMILES: CC(C)CC1OC(=O)C(C(C)C)NC(=O)C(C(C)C)OC(=O)C(C)NC(=O)C(CC(C)C)OC(=O)C(C(C)C)NC(=O)C(C(C)C)OC(=O)C(C)NC(=O)C(CC(C)C)OC(=O)C(C(C)C)NC(=O)C(C(C)C)OC(=O)C(C)NC1=O

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Encyclopedic overview

4 sections

Contents

Biosynthesis
In the news
References
External links

Cereulide is a heat-stable toxin produced by some strains of Bacillus cereus, B. megaterium and related species. It is a potent cytotoxin that destroys mitochondria. It causes nausea and vomiting.

Cereulide acts as an ionophore with a high affinity for potassium cations. Exposure to cereulide causes loss of the membrane potential and uncoupling of oxidative phosphorylation in the mitochondria. The nausea and vomiting is believed to be caused by cereulide's binding and activation of 5-HT3 receptors, leading to increased afferent vagus nerve stimulation.

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