Alamethicin

Alamethicin is a channel-forming peptide antibiotic, produced by the fungus Trichoderma viride. It belongs to peptaibol peptides which contain the non-proteinogenic amino acid residue Aib (2-aminoisobutyric acid). This residue strongly induces formation of alpha-helical structure. The peptide sequence is

In the Vinony graph

Within Vinony's link graph, Alamethicin is referenced by 16 other articles, and connects out to molecule, antibiotic and ethanol.

Vinony files it under Antimicrobial peptides, Chembox image size set and Chemical articles with multiple compound IDs.

Its subject is documented across 7 Wikipedia language editions.

Chemical data

Formula: C92H150N22O25
Molecular weight: 1964.3 g/mol
IUPAC name: (4S)-4-[[2-[[2-[[(2S)-2-[[(2S)-1-[2-[[(2S)-2-[[2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[2-[[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]-2-methylpropanoyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-5-[[(2S)-5-amino-1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-oxopentanoic acid
SMILES: C[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)NC(C)(C)C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC2=CC=CC=C2)CO)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]3CCCN3C(=O)C(C)(C)NC(=O)C
InChIKey: LGHSQOCGTJHDIL-UTXLBGCNSA-N
XLogP: -1.8
Polar surface area: 708 Å²
H-bond donors: 22
H-bond acceptors: 25
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

1,264 papers

The conformational properties of alamethicin in ethanol studied by NMR.European biophysics journal : EBJ · 2024
Alamethicin channel inactivation caused by voltage-driven flux of alamethicin.Biochimica et biophysica acta. Biomembranes · 2024
Alamethicin and related membrane channel forming polypeptides.Molecular and cellular biochemistry · 1983
The history of alamethicin: a review of the most extensively studied peptaibol.Chemistry & biodiversity · 2007
Alamethicin: a peptide model for voltage gating and protein-membrane interactions.Annual review of biophysics and biomolecular structure · 1994

via PubMed

Wikidata facts

Subclass of: nonribosomal peptide
Mass: 1963.114248299999

Show 3 more facts

chemical formula: C₉₂H₁₅₀N₂₂O₂₅
isomeric SMILES: CC(C)C[C@@H](C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC2=CC=CC=C2)CO)NC(=O)CNC(=O)C(C)(C)NC(=O)[C@H](C(C)C)NC(=O)C(C)(C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]3CCCN3C(=O)C(C)(C)NC(=O)C
canonical SMILES: CC(=O)NC(C)(C)C(=O)N1CCCC1C(=O)NC(C)(C)C(=O)NC(C)C(=O)NC(C)(C)C(=O)NC(C)C(=O)NC(CCC(N)=O)C(=O)NC(C)(C)C(=O)NC(C(=O)NC(C)(C)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(C)(C)C(=O)N1CCCC1C(=O)NC(C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(N)=O)C(=O)NC(CO)Cc1ccccc1)C(C)C)C(C)C

Sources (2)

via Wikidata · CC0

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