Amanullin

Amanullin

Names
Other names 3-Isoleucine-alpha-amanitin
Identifiers
CAS Registry Number	21803-57-6 Y
ChemSpider	102814 Y
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
Jmol-3D images	Image Image
PubChem	114856
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
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. 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. 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