Chemistry:epsilon-Amanitin

Short description: Cyclic peptide part of a group of toxins present in Amanita mushrooms

ε-Amanitin

Names
Other names Amanine
Identifiers
CAS Number	21705-02-2 Y
3D model (JSmol)	Interactive image
ChemSpider	26234941 Y
PubChem CID	30508
InChI 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 Y Key: OFILNAORONITPV-ZUROAWGWSA-N Y 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
SMILES 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
Chemical formula	C39H53N9O14S
Molar mass	903.96 g/mol
Appearance	Colorless, crystalline solid
Solubility in water	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).
Y verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

epsilon-Amanitin or ε-amanitin is a cyclic peptide. It is an amatoxin, all of which are found in several members of the mushroom genus Amanita. The oral -1">50 of ε-amanitin is approximately 0.1 mg/kg.

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.

See also

• Mushroom poisoning

External links

• Amatoxins REVISED
• Poisonous Mushrooms (German)