Amanullinic acid

Amanullinic acid is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in several members of the mushroom genus Amanita. Amanullinic acid is relatively non-toxic( oral LD50 >20 mg/kg in mice).[1]

Amanullinic acid
Names
Other names
1-L-Aspartic acid-3-isoleucine-alpha-amanitin
Identifiers
3D model (JSmol)
ChemSpider
  • 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) Y
    Key: HFENEIQMWRYNGK-UHFFFAOYSA-N Y
  • 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
  • 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)CC)([H])N[C@@]4=O)=O
Properties
C39H53N9O13S
Molar mass 887.96 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Toxicology

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

See also

References
  1. T. Wieland; Faulstich H. (1978). "Amatoxins, Phallotoxins, Phallolysin, and Antamanide: the Biologically Active Components of Poisonous Amanita Mushrooms". CRC Critical Reviews in Biochemistry. 5 (3): 185–260. doi:10.3109/10409237809149870. PMID 363352.
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