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Amanullinic acid

Names
Other names 1-L-Aspartic acid-3-isoleucine-alpha-amanitin
Identifiers
CAS Number	54532-45-5
3D model (JSmol)	Interactive image Interactive image
ChemSpider	149798
PubChem CID	171349
InChI InChI=1S/C39H53N9O13S/c1-5-17(3)31-36(58)41-13-28(51)42-26-16-62(61)38-22(21-8-7-19(49)9-23(21)45-38)11-24(33(55)40-14-29(52)46-31)43-37(59)32(18(4)6-2)47-35(57)27-10-20(50)15-48(27)39(60)25(12-30(53)54)44-34(26)56/h7-9,17-18,20,24-27,31-32,45,49-50H,5-6,10-16H2,1-4H3,(H,40,55)(H,41,58)(H,42,51)(H,43,59)(H,44,56)(H,46,52)(H,47,57)(H,53,54)Key: HFENEIQMWRYNGK-UHFFFAOYSA-N InChI=1/C39H53N9O13S/c1-5-17(3)31-36(58)41-13-28(51)42-26-16-62(61)38-22(21-8-7-19(49)9-23(21)45-38)11-24(33(55)40-14-29(52)46-31)43-37(59)32(18(4)6-2)47-35(57)27-10-20(50)15-48(27)39(60)25(12-30(53)54)44-34(26)56/h7-9,17-18,20,24-27,31-32,45,49-50H,5-6,10-16H2,1-4H3,(H,40,55)(H,41,58)(H,42,51)(H,43,59)(H,44,56)(H,46,52)(H,47,57)(H,53,54)Key: HFENEIQMWRYNGK-UHFFFAOYAM
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)CC)()N4=O)=O O=C2N1CC(O)CC1C(=O)NC(C(=O)NC5C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CC(=O)O)CS(=O)c4c(c3ccc(O)cc3n4)C5)C(C)CC)C(C)CC
Properties
Chemical formula	C39H53N9O13S
Molar mass	887.96 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Amanullinic acid 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 amanullinic acid is approximately 0.1 mg/kg in mice.

Toxicology

Like other amatoxins, amanullinic acid is an inhibitor of RNA polymerase II.

See also

• Mushroom poisoning

References

1. T. Wieland and Faulstich H. (1978). "Amatoxins, Phallotoxins, Phallolysin, and Antamanide: the Biologically Active Components of Poisonous Amanita Mushrooms". CRC Critical Reviews in Biochemistry. 5 (3): 185. doi:10.3109/10409237809149870. PMID 363352.

External links

• Amatoxins REVISED

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