epsilon-Amanitin

ε-Amanitin

Other names Amanine
Identifiers
CAS number	21705-02-2
PubChem	30508
ChemSpider	26234941^Y
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C₃₉H₅₃N₉O₁₄S
Molar mass	903.96 g/mol
Appearance	Colorless, crystalline solid
Solubility in water	Soluble
Solubility in ethanol and methanol	Soluble
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

1 Toxicology
2 References
3 See also
4 External links

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. 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

Other compounds	Antamanide Phallolysin Toxophallin

sect.
Lepidella

Species	A. abrupta 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 (enterotoxin/neurotoxin/hemotoxin/cardiotoxin/phototoxin)

Bacterial toxins

Exotoxin

Gram positive

Bacilli	Clostridium: tetani (Tetanospasmin) · 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, SEB)

Actinobacteria	Cord factor · Diphtheria toxin