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Amaninamide
Sign in to saveAlso known as 4-(2-mercapto-L-tryptophan)-alpha-Amanitin
Amaninamide is a cyclic peptide. It is one of the amatoxins, all of which are found in several members of the mushroom genera Amanita, Lepiota and Galerina. It differs from alpha-amanitin in lacking the hydroxyl group on tryptophan. This alters its UV absorption spectrum but not its toxicity.
Chemical data
- Formula
- C39H54N10O13S
- Molecular weight
- 903 g/mol
- IUPAC name
- 2-[(8R,27R)-34-butan-2-yl-13-[(2S,3S)-3,4-dihydroxybutan-2-yl]-8-hydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetamide
- SMILES
- CCC(C)C1C(=O)NCC(=O)NC2C[S@@](=O)C3=C(CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C4C[C@H](CN4C(=O)C(NC2=O)CC(=O)N)O)[C@H](C)[C@@H](CO)O)C5=CC=CC=C5N3
- InChIKey
- BOHCOUQZNDPURZ-OTYBJSEPSA-N
- XLogP
- -4.1
- Polar surface area
- 380 Ų
- H-bond donors
- 12
- H-bond acceptors
- 14
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 902.359253
Show 4 more facts
- chemical formula
- C₃₉H₅₄N₁₀O₁₃S
- canonical SMILES
- CCC(C)C1C(=O)NCC(=O)NC2CS(=O)C3=C(CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)CC(=O)N)O)C(C)C(CO)O)C5=CC=CC=C5N3
- found in taxon
- Amanita virosa
- isomeric SMILES
- CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4ccccc34)[S@+]([O-])CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N1C[C@H](O)CC1C(=O)NC([C@H](C)[C@H](O)CO)C(=O)N2
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Toxicology
- See also
- References
- External links
Amaninamide is a cyclic peptide. It is one of the amatoxins, all of which are found in several members of the mushroom genera Amanita, Lepiota and Galerina. It differs from alpha-amanitin in lacking the hydroxyl group on tryptophan. This alters its UV absorption spectrum but not its toxicity.
==Toxicology==
Excerpted from Wikipedia’s “Amaninamide” article, available under the CC BY-SA 4.0 licence.