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ε-Amanitin

Names
Other names Amanine
Identifiers
CAS Number	21705-02-2
3D model (JSmol)	Interactive image
ChemSpider	26234941
PubChem CID	30508
CompTox Dashboard (EPA)	DTXSID201028142
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/s1Key: OFILNAORONITPV-ZUROAWGWSA-N 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/s1Key: OFILNAORONITPV-ZUROAWGWBI
SMILES O=C(NCC(N(C(NCC(N(C3)C(N(CC(O)=O)C(N54C(O)C5)=O)=O)=O)=O)()(C)CC)=O)(CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC(((C)(O)C)()N4=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 , 100 kPa). Y verify (what is  ?) Infobox references

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

Toxicology

Like other amatoxins, ε-amanitin 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.

References

1. M. Cochet-Meillhac and 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. PMID 4601749.

See also

• Mushroom poisoning

External links

• Amatoxins REVISED
• Poisonous Mushrooms (German)

v t e Poisonous Amanita mushrooms
Subgenus Amanita	Amanita Species A. albocreata A. crenulata A. farinosa A. frostiana A. gemmata A. ibotengutake A. multisquamosa A. muscaria A. pantherina A. porphyria A. regalis A. strobiliformis A. xanthocephala Compounds Toxins: Ibotenic Acid Muscimol Other compounds: Muscarine Muscazone Amavadine
Subgenus Amanitina	Lepidella (=Saproamanita) Species A. thiersii Compounds unknown toxin Phalloideae Species Destroying angels A. bisporigera A. exitialis A. magnivelaris A. ocreata A. verna A. virosa A. virosiformis Other members A. arocheae A. fuliginea A. fuligineoides A. pallidorosea A. phalloides A. rimosa A. subjunquillea Compounds Amatoxins Amanitins alpha- beta- gamma- epsilon- Amanullin Amanullinic acid Amaninamide Amanin Proamanullin Phallotoxins Phallacidin Phallacin Phallisacin Phallisin Phalloidin Phalloin Prophalloin Virotoxins Alaviroidin Viroisin Deoxoviroisin Viroidin Deoxoviroidin Other compounds Antamanide Phallolysin Toxophallin Roanokenses Species A. proxima A. smithiana A. sphaerobulbosa Compounds Allenic norleucine (2-amino-4,5-hexadienoic acid) Propargylglycine Validae Species A. rubescens (A. amerirubescens nom. prov.) Compounds Rubescenslysin

• Peptides
• Amatoxins
• Hepatology
• Indoles