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Substance Name: alpha-Amanitin
RN: 23109-05-9
UNII: E04K0QZ999
InChIKey: CIORWBWIBBPXCG-SXZCQOKQSA-N

Note

  • A cyclic octapeptide with a thioether bridge between the cystine and tryptophan. It inhibits RNA POLYMERASE II. Poisoning may require LIVER TRANSPLANTATION.

Molecular Formula

  • C39-H54-N10-O14-S

Molecular Weight

  • 918.9697
 

Classification Codes

  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Poisons
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Names and Synonyms

Name of Substance

  • alpha-Amanitin

MeSH Heading

  • Alpha-Amanitin

Synonyms

  • alpha-Amanitin
  • alpha-Amanitine
  • alpha-Amatoxin
  • BRN 1071138
  • Cyclic(L-asparaginyl-4-hydroxy-L-prolyl-(R)-4,5-dihydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl), cyclic (4-8)-sulfide, (R)-S-oxide
  • EINECS 245-432-2
  • HSDB 3458
  • UNII-E04K0QZ999

Systematic Names

  • 9,18-(Iminoethaniminoethaniminoethaniminomethano)pyrrolo(1',2':8,9)(1,5,8,11,14)thiatetraazacyclooctadecino(18,17-b)indole, cyclic peptide deriv.
  • alpha-Amanitin
  • alpha-Amanitine

Registry Numbers

CAS Registry Number

  • 23109-05-9

FDA UNII

  • E04K0QZ999

Other Registry Numbers

  • 11000-43-4
  • 21150-20-9
  • 21373-20-6
  • 21373-21-7
  • 31098-01-8
  • 82346-97-2

System Generated Number

  • 0023109059

Structure Descriptors

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

InChIKey

CIORWBWIBBPXCG-SXZCQOKQSA-N

Smiles

CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@@H]2Cc3c([nH]c4cc(O)ccc34)[S@+]([O-])C[C@H](NC(=O)CNC1=O)C(=O)N[C@@H](CC(=O)N)C(=O)N5C[C@H](O)C[C@H]5C(=O)N[C@@H]([C@@H](C)[C@@H](O)CO)C(=O)N2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100ug/kg (0.1mg/kg)   New England Journal of Medicine. Vol. 269, Pg. 223, 1963.
mouse LD50 unreported 300ug/kg (0.3mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 2142, 1972.