Amanullin

Amanullin 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 amanullin is approximately 20 mg/kg in mice; however, it is non-toxic in humans.

Amanullin

Names
Other names 3-Isoleucine-alpha-amanitin
Identifiers
CAS Number	21803-57-6^Y
3D model (JSmol)	Interactive image
ChemSpider	102814^Y
PubChem CID	114856
InChI 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)^Y Key: QQLVIKWYAVVKKF-UHFFFAOYSA-N^Y
SMILES 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
Properties
Chemical formula	C39H54N10O12S
Molar mass	886.86 g/mol
Appearance	Colorless, crystalline solid
Solubility in water	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).
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Infobox references

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

• Mushroom poisoning

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.

External links

• Amatoxins REVISED
• Poisonous Mushrooms (German)