ε-Amanitin

ε-Amanitin (epsilon-Amanitin) is a cyclic peptide. It is an amatoxin, all of which are found in several members of the mushroom genus Amanita. The oral LD50 of ε-amanitin is approximately 0.1 mg/kg.

ε-Amanitin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)/t16-,17-,18-,20+,24-,25-,26-,27-,31-,32-,63?/m0/s1 checkY
    Key: OFILNAORONITPV-ZUROAWGWSA-N checkY
  • InChI=1/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)/t16-,17-,18-,20+,24-,25-,26-,27-,31-,32-,63?/m0/s1
    Key: OFILNAORONITPV-ZUROAWGWBI
  • O=C(NCC(N[C@@](C(NCC(N[C@@H](C3)C(N[C@@H](CC(O)=O)C(N5[C@H]4C[C@@H](O)C5)=O)=O)=O)=O)([H])[C@@H](C)CC)=O)[C@H](CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC([C@@]([C@@H](C)[C@@H](O)C)([H])N[C@@]4=O)=O
Properties
C39H53N9O14S
Molar mass 903.96 g/mol
Appearance Colorless, crystalline solid
Soluble
Solubility in ethanol and methanol Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Toxicology

Like other amatoxins, ε-amanitin is an inhibitor of RNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme which completely prevents mRNA synthesis, effectively causing cytolysis of hepatocytes (liver cells) and kidney cells.[1]

See also

References
  1. M. Cochet-Meillhac; Chambon P. (1974). "Animal DNA-dependent RNA polymerases. 11. Mechanism of the inhibition of RNA polymerases B by amatoxins". Biochim Biophys Acta. 353 (2): 160–184. doi:10.1016/0005-2787(74)90182-8. PMID 4601749.
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