α-Amanitin

α-Amanitin
Names
	Other names (cyclic L-asparaginyl-4-hydroxy-L-proly-(R)-4,5-dihydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl) cyclic (4 → 8)-sulfide(R)-S-oxide.
Identifiers
CAS Number	23109-05-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37415 ;
ChemSpider	16735655 ;
ECHA InfoCard	100.041.287
PubChem CID	2100;
UNII	E04K0QZ999 ;
CompTox Dashboard (EPA)	DTXSID1036709 ;
	InChI InChI=1S/C39H54N10O14S/c1-4-16(2)31-36(60)42-11-29(55)43-25-15-64(63)38-21(20-6-5-18(51)7-22(20)46-38)9-23(33(57)41-12-30(56)47-31)44-37(61)32(17(3)27(53)14-50)48-35(59)26-8-19(52)13-49(26)39(62)24(10-28(40)54)45-34(25)58/h5-7,16-17,19,23-27,31-32,46,50-53H,4,8-15H2,1-3H3,(H2,40,54)(H,41,57)(H,42,60)(H,43,55)(H,44,61)(H,45,58)(H,47,56)(H,48,59)/t16?,17?,19?,23-,24-,25-,26-,27-,31-,32-,64+/m0/s1 Key: CIORWBWIBBPXCG-NUCBJAHASA-N ;
	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)[C@@H](O)CO)([H])N[C@@]4=O)=O;
Properties
Chemical formula	C39H54N10O14S
Molar mass	918.97 g/mol
Solubility in water	Good
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic
	GHS labelling:
Pictograms
Hazard statements	H300, H310, H330, H373
Precautionary statements	P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

α-Amanitin (alpha-Amanitin) is a cyclic peptide of eight amino acids. It is possibly the most deadly of all the amatoxins, toxins found in several species of the mushroom genus Amanita, one being the death cap (Amanita phalloides) as well as the destroying angel, a complex of similar species, principally A. virosa and A. bisporigera. It is also found in the mushrooms Galerina marginata, Lepiota subincarnata and Conocybe rugosa. The oral LD₅₀ of amanitin is 100 μg/kg for rats.

Unlike most cyclic peptides, amatoxins (and phallotoxins) are synthesized on ribosomes. The genes encoding the proprotein for α-amanitin belong to the same family as those that encode for phallacidin (a phallotoxin).^[1]

^ Hallen HE, Luo H, Scott-Craig JS, Walton JD (November 2007). "Gene family encoding the major toxins of lethal Amanita mushrooms". Proceedings of the National Academy of Sciences of the United States of America. 104 (48): 19097–101. Bibcode:2007PNAS..10419097H. doi:10.1073/pnas.0707340104. PMC 2141914. PMID 18025465.

[1] Hallen HE, Luo H, Scott-Craig JS, Walton JD (November 2007). "Gene family encoding the major toxins of lethal Amanita mushrooms". Proceedings of the National Academy of Sciences of the United States of America. 104 (48): 19097–101. Bibcode:2007PNAS..10419097H. doi:10.1073/pnas.0707340104. PMC 2141914. PMID 18025465.

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