Amanullin

Amanullin

Names
Other names 3-Isoleucine-alpha-amanitin
Identifiers
CAS Number	21803-57-6 Y
3D model (Jmol)	Interactive image Interactive image
ChemSpider	102814 Y
PubChem	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 O=C2N1CC(O)CC1C(=O)NC(C(=O)NC5C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CC(=O)N)CS(=O)c4c(c3ccc(O)cc3n4)C5)C(C)CC)C(C)CC
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).
Y verify (what is YN ?)
Infobox references

Amanullin is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in several members of the Amanita genus of mushrooms. The oral LD₅₀ of amanullin is approximately 20 mg/kg in mice, however it is non-toxic in humans.

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

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. Phalloideae	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. Roanokenses	Species A. proxima A. smithiana A. sphaerobulbosa Compounds Allenic norleucine (2-amino-4,5-hexadienoic acid) Propargylglycine
sect. Validae	Species A. rubescens (A. amerirubescens nom. prov.) Compounds Rubescenslysin
sect. Lepidella	Species A. thiersii Compounds unknown toxin