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CAS 26645-35-2

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phallacidin from amanita phalloides

Description:
Phallacidin is a potent cyclic peptide toxin derived from the mushroom Amanita phalloides, commonly known as the death cap mushroom. It is classified as a member of the amatoxin family, which are known for their high toxicity and ability to inhibit RNA polymerase II, leading to severe liver and kidney damage. Phallacidin is characterized by its ability to bind to actin filaments, disrupting cytoskeletal integrity and cellular function. The compound is typically found in trace amounts in the mushroom and is not as well-known as its more infamous counterpart, alpha-amanitin. Phallacidin is soluble in water and exhibits a relatively stable structure under physiological conditions. Due to its high toxicity, it poses significant health risks if ingested, and its effects can be lethal. Research on phallacidin is primarily focused on understanding its mechanism of action and potential applications in cellular biology, particularly in studies involving the cytoskeleton and cell motility. Caution is advised when handling or studying this compound due to its hazardous nature.
Formula:C36H48N8O12S
InChI:InChI=1/C36H48N8O12S/c1-15(2)25-31(51)43-26(35(54)55)32(52)40-23-13-57-33-19(18-7-5-6-8-20(18)41-33)10-21(28(48)39-22(29(49)42-25)11-36(4,56)14-45)38-27(47)16(3)37-30(50)24-9-17(46)12-44(24)34(23)53/h5-8,15-17,21-26,41,45-46,56H,9-14H2,1-4H3,(H,37,50)(H,38,47)(H,39,48)(H,40,52)(H,42,49)(H,43,51)(H,54,55)/t16-,17?,21-,22-,23-,24-,25?,26-,36-/m0/s1
SMILES:CC(C)C1C(=N[C@@H](C(=N[C@H]2CSc3c(C[C@@H](C(=N[C@@H](C[C@@](C)(CO)O)C(=N1)O)O)N=C([C@H](C)N=C([C@@H]1CC(CN1C2=O)O)O)O)c1ccccc1[nH]3)O)C(=O)O)O
Synonyms:
  • Phallacidin
  • (3aS,6S,9S,18R,23S,29S)-29-[(2S)-2,3-dihydroxy-2-methylpropyl]-2-hydroxy-6-methyl-4,7,19,22,25,28,31-heptaoxo-26-(propan-2-yl)-1,2,3,3a,4,5,6,7,8,9,10,15,18,19-tetradecahydro-17H-18,9-(epiminoethanoiminoethanoiminoethanoiminomethano)pyrrolo[1',2':5,6][1,5,8,11]thiatriazacyclopentadecino[15,14-b]indole-23-carboxylic acid
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