epsilon-Amanitin

ε-Amanitin
Names

Other names Amanine
Identifiers
CAS Number	21705-02-2^Y
ChemSpider	26234941^Y
Jmol interactive 3D	Image
PubChem	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

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.^[1]

References

↑ 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. doi:10.1016/0005-2787(74)90182-8. PMID 4601749.

External links

Amatoxins REVISED
Poisonous Mushrooms (German)

Poisoning from Amanitas

sect.
Amanita

Species	A. albocreata A. crenulata A. farinosa A. frostiana A. gemmata A. multisquamosa A. muscaria A. pantherina A. porphyria A. regalis A. strobiliformis A. xanthocephala

Compounds	Toxins: Ibotenic Acid Muscimol Other compounds: Muscarine Muscazone Amavadine

sect.
Phalloidea

Species

Destroying angels	A. bisporigera A. exitialis A. magnivelaris A. ocreata A. verna A. virosa A. virosiformis

Other members	A. arocheae A. phalloides A. subjunquilea

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

sect.
Lepidella

Species	A. nauseosa A. proxima A. smithiana A. sphaerobulbosa A. thiersii

Compounds	Allenic norleucine (2-amino-4,5-hexadienoic acid) Propargylglycine

sect.
Validae

Species	A. rubescens (A. amerirubescens nom. prov.)

Compounds	Rubescenslysin

Toxins

Clostridium:	tetani Tetanospasmin Tetanolysin perfringens Alpha toxin Enterotoxin difficile A B botulinum Botox

other:	Anthrax toxin Listeriolysin O

Cocci

Streptolysin Leukocidin Panton-Valentine leukocidin

Staphylococcus	Staphylococcus aureus alpha/beta/delta Exfoliatin Toxic shock syndrome toxin Staphylococcal Enterotoxin B (SEB)

Plant toxins

Invertebrate toxins

scorpion:	Androctonus australis hector insect toxin Charybdotoxin Maurotoxin Agitoxin Margatoxin Slotoxin Scyllatoxin Hefutoxin Lq2 Birtoxin Bestoxin BmKAEP Phaiodotoxin Imperatoxin Pi3

spider:	Latrotoxin Alpha-latrotoxin CSTX Cupiennins PhTx3 Stromatoxin Vanillotoxin Huwentoxin

mollusca:	Conotoxin Eledoisin Onchidal Saxitoxin Tetrodotoxin

Vertebrate toxins

fish:	Ciguatera Tetrodotoxin

amphibian:	(+)-Allopumiliotoxin 267A Batrachotoxin Bufotoxins Arenobufagin Bufotalin Bufotenin Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin

reptile/snake venom:	Bungarotoxin Alpha-Bungarotoxin Beta-Bungarotoxin Calciseptine Taicatoxin Calcicludine Cardiotoxin III

note: some toxins are produced by lower species and pass through intermediate species

Category
Commons
WikiProject

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epsilon-Amanitin

Toxicology

See also

References

External links