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CHEBI:37415 - α-amanitin

ChEBI IDCHEBI:37415
ChEBI Nameα-amanitin
Stars
ASCII Namealpha-amanitin
DefinitionA heterodetic cyclic peptide consisting of eight amino acid residues and containing a thioether bridge between a cysteine and a tryptophan residue. It is found in a number of poisonous mushrooms, including Amanita phalloides (the death cap), Galerina marginata, and and Conocybe filaris.
Secondary ChEBI IDsCHEBI:10207, CHEBI:37414
Last Modified28 July 2014
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC39H54N10O14S
Net Charge0
Average Mass918.984
Monoisotopic Mass918.35417
SMILES[H][C@@]12C[C@@H](O)CN1C(=O)[C@H](CC(N)=O)NC(=O)[C@]1([H])C[S@@](=O)c3nc4cc(O)ccc4c3C[C@]([H])(NC(=O)[C@]([H])([C@@H](C)[C@@H](O)CO)NC2=O)C(=O)NCC(=O)N[C@@]([H])([C@@H](C)CC)C(=O)NCC(=O)N1
InChIInChI=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
InChIKeyCIORWBWIBBPXCG-SXZCQOKQSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
mycotoxin  Poisonous substance produced by fungi.
EC 2.7.7.6 (RNA polymerase) inhibitor  An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6).
ChEBI Ontology
Outgoing Relation(s)
α-amanitin (CHEBI:37415) has role EC 2.7.7.6 (RNA polymerase) inhibitor (CHEBI:37416)
α-amanitin (CHEBI:37415) has role mycotoxin (CHEBI:25442)
α-amanitin (CHEBI:37415) is a heterodetic cyclic peptide (CHEBI:24533)
IUPAC Name 
1,8-anhydro-S1,C2.5-cyclo[L-cysteinyl-L-asparaginyl-trans-4-hydroxy-L-prolyl-(R)-4,5-dihydroxy-L-isoleucyl-6-hydroxy-L-tryptophylglycyl-L-isoleucylglycine] (R)-S1-oxide
Synonyms  Source
alpha-AmanitinKEGG COMPOUND
alpha-AmanitineChemIDplus
alpha-AmatoxinChemIDplus
Manual XrefsDatabases
C08438KEGG COMPOUND
Alpha-amanitinWikipedia
C00001516KNApSAcK
Registry NumbersSources
Reaxys:1071138Reaxys
CAS:23109-05-9KEGG COMPOUND
CAS:23109-05-9ChemIDplus
Citations