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Amanullin

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Amanullin
Names
Other names
3-Isoleucine-alpha-amanitin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C39H54N10O12S/c1-5-17(3)31-36(58)42-13-29(53)43-26-16-62(61)38-22(21-8-7-19(50)9-23(21)46-38)11-24(33(55)41-14-30(54)47-31)44-37(59)32(18(4)6-2)48-35(57)27-10-20(51)15-49(27)39(60)25(12-28(40)52)45-34(26)56/h7-9,17-18,20,24-27,31-32,46,50-51H,5-6,10-16H2,1-4H3,(H2,40,52)(H,41,55)(H,42,58)(H,43,53)(H,44,59)(H,45,56)(H,47,54)(H,48,57) checkY
    Key: QQLVIKWYAVVKKF-UHFFFAOYSA-N checkY
  • O=C(NCC(N[C@@](C(NCC(N[C@@H](C3)C(N[C@@H](CC(N)=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)CC)([H])N[C@@]4=O)=O
  • O=C2N1CC(O)CC1C(=O)NC(C(=O)NC5C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CC(=O)N)CS(=O)c4c(c3ccc(O)cc3n4)C5)C(C)CC)C(C)CC
Properties
C39H54N10O12S
Molar mass 886.86 g/mol
Appearance Colorless, crystalline solid
Soluble
Solubility in ethanol, methanol Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Amanullin is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in several members of the Amanita genus of mushrooms. The oral LD50 of amanullin is approximately 20 mg/kg in mice, however it is non-toxic in humans.

Toxicology

Like other amatoxins, amanullin is an inhibitor of RNA polymerase II. Amanullin has a species dependent and specific attraction to the enzyme RNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme, effectively causing cytolysis of hepatocytes (liver cells).[1]

See also

References

  1. ^ Cochet-Meilhac M, Chambon P (June 1974). "Animal DNA-dependent RNA polymerases. 11. Mechanism of the inhibition of RNA polymerases B by amatoxins". Biochim. Biophys. Acta. 353 (2): 160–84. doi:10.1016/0005-2787(74)90182-8. PMID 4601749.
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