Structure via PubChem · Public domain (PubChem)
α-amanitin
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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 of amanitin is 100 μg/kg for rats.
Chemical data
- Formula
- C39H54N10O14S
- Molecular weight
- 919 g/mol
- IUPAC name
- 2-[(1R,4S,8R,10S,13S,16S,27R,34S)-34-[(2S)-butan-2-yl]-13-[(2R,3R)-3,4-dihydroxybutan-2-yl]-8,22-dihydroxy-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(24),20,22-tetraen-4-yl]acetamide
- SMILES
- CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H]2C[S@@](=O)C3=C(C[C@@H](C(=O)NCC(=O)N1)NC(=O)[C@@H](NC(=O)[C@@H]4C[C@H](CN4C(=O)[C@@H](NC2=O)CC(=O)N)O)[C@@H](C)[C@H](CO)O)C5=C(N3)C=C(C=C5)O
- InChIKey
- CIORWBWIBBPXCG-SXZCQOKQSA-N
- XLogP
- -4.4
- Polar surface area
- 400 Ų
- H-bond donors
- 13
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Research
1,975 papers- Mechanism and treatment of α-amanitin poisoning.Archives of toxicology · 2023
- Understanding α-amanitin hepatotoxicity: Mechanisms from cellular models.Toxicology · 2025
- Total Synthesis of α- and β-Amanitin.Angewandte Chemie (International ed. in English) · 2020
- PP2A attenuates α-amanitin-induced liver injury by promoting autophagy and inhibiting apoptosis in mouse models.Chemico-biological interactions · 2025
- α-amanitin induces autophagy through AMPK-mTOR-ULK1 signaling pathway in hepatocytes.Toxicology letters · 2023
via PubMed
Wikidata facts
- Mass
- 918.354167
Show 4 more facts
- Commons category
- Alpha-Amanitin
- chemical formula
- C₃₉H₅₄N₁₀O₁₄S
- isomeric SMILES
- CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H]2C[S@@](=O)C3=C(C[C@@H](C(=O)NCC(=O)N1)NC(=O)[C@@H](NC(=O)[C@@H]4C[C@H](CN4C(=O)[C@@H](NC2=O)CC(=O)N)O)[C@@H](C)[C@H](CO)O)C5=C(N3)C=C(C=C5)O
- 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=C(N3)C=C(C=C5)O
Sources (1)
via Wikidata · CC0
~9 min read
Article
11 sectionsContents
- Scientific use
- Chemical structure
- Detection techniques
- Biosynthesis
- Total synthesis
- Symptoms of poisoning
- Mode of inhibitory action
- Use in antibody-drug conjugates
- See also
- References
- External links
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 of amanitin is 100 μg/kg for rats.
Amatoxins (and phallotoxins) are part of the RiPP class of natural products. The genes encoding the proprotein for α-amanitin belong to the same family as those that encode for phallacidin (a phallotoxin).