CHEBI:37415 - α-amanitin

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ChEBI Name α-amanitin
ChEBI ID CHEBI:37415
ChEBI ASCII Name alpha-amanitin
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:37414, CHEBI:10207
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Formula C39H54N10O14S
Net Charge 0
Average Mass 918.97106
Monoisotopic Mass 918.354
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
InChIKey CIORWBWIBBPXCG-SXZCQOKQSA-N
SMILES [H][C@]12Cc3c([nH]c4cc(O)ccc34)[S@](=O)C[C@]([H])(NC(=O)CNC(=O)[C@@]([H])(NC(=O)CNC1=O)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N1C[C@H](O)C[C@@]1([H])C(=O)N[C@@]([H])([C@@H](C)[C@@H](O)CO)C(=O)N2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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).
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ChEBI Ontology
Outgoing 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 Sources
alpha-Amanitin KEGG COMPOUND
alpha-Amanitine ChemIDplus
alpha-Amatoxin ChemIDplus
Manual Xrefs Databases
Alpha-amanitin Wikipedia
C00001516 KNApSAcK
C08438 KEGG COMPOUND
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Registry Numbers Types Sources
1071138 Reaxys Registry Number Reaxys
1071138 Beilstein Registry Number Beilstein
23109-05-9 CAS Registry Number KEGG COMPOUND
23109-05-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
28 July 2014