Amaninamide

Names
Other names 4-(2-mercapto-L-tryptophan)-alpha-Amanitin
Identifiers
CAS Number	58311-65-2 Y
3D model (JSmol)	Interactive image
ChemSpider	2299516 Y
PubChemCID	3035225
UNII	A0W351848Z Y
InChI InChI=1S/C39H54N10O13S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-63(62)38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58) Y Key: BOHCOUQZNDPURZ-UHFFFAOYSA-N Y InChI=1/C39H54N10O13S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-63(62)38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58) Key: BOHCOUQZNDPURZ-UHFFFAOYAZ
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=C2)NC([C@@]([C@@H](C)[C@@H](O)CO)([H])N[C@@]4=O)=O
Properties
Chemical formula	C39H54N10O13S
Molar mass	902.97 g/mol
Appearance	Colorless, crystalline solid
Solubility in water	Soluble
Solubility inethanol,methanol	Soluble
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Amaninamide is acyclic peptide. It is one of theamatoxins, all of which are found in several members of themushroom generaAmanita,Lepiota andGalerina. It differs from alpha-amanitin in lacking the hydroxyl group on tryptophan. This alters its UV absorption spectrum but not its toxicity.

Like other amatoxins, amaninamide is an inhibitor ofRNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme which completely preventsmRNA synthesis, effectively causingcytolysis ofhepatocytes (liver cells) andkidney cells.^[1]

• Mushroom poisoning

• Amatoxins REVISEDArchived 2009-01-13 at theWayback Machine
• Poisonous Mushrooms (German)

• Peptides
• Amatoxins
• Hepatotoxins
• Cyclic peptides

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