Structure via PubChem · Public domain (PubChem)
antamanide
Sign in to saveAntamanide is a cyclic decapeptide isolated from a fungus, the death cap: Amanita phalloides. It was being studied in 1995 as a potential anti-toxin against the effects of phalloidin and for its potential for treating edema. It contains 1 valine residue, 4 proline residues, 1 alanine residue, and 4 phenylalanine residues with a structure of c(Val-Pro-Pro-Ala-Phe-Phe-Pro-Pro-Phe-Phe). It was isolated by determining the source of the anti-phalloidin activity from a lipophillic extraction from the organism. It has been shown that antamanide can react to form alkali metal ion complexes. These incl
Chemical data
- Formula
- C64H78N10O10
- Molecular weight
- 1147.4 g/mol
- IUPAC name
- (3S,9S,12S,15S,18S,24S,30S,33S,36S,39S)-9,12,33,36-tetrabenzyl-15-methyl-30-propan-2-yl-1,7,10,13,16,22,28,31,34,37-decazapentacyclo[37.3.0.03,7.018,22.024,28]dotetracontane-2,8,11,14,17,23,29,32,35,38-decone
- SMILES
- C[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N4CCC[C@H]4C(=O)N5CCC[C@H]5C(=O)N1)C(C)C)CC6=CC=CC=C6)CC7=CC=CC=C7)CC8=CC=CC=C8)CC9=CC=CC=C9
- InChIKey
- WTINJQXJTHUFRF-IHTIUHOMSA-N
- XLogP
- 6
- Polar surface area
- 256 Ų
- H-bond donors
- 6
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Research
101 papers- Antamanide Analogs as Potential Inhibitors of Tyrosinase.International journal of molecular sciences · 2022
- Antamanide, a derivative of Amanita phalloides, is a novel inhibitor of the mitochondrial permeability transition pore.PloS one · 2011
- Amatoxins, phallotoxins, phallolysin, and antamanide: the biologically active components of poisonous Amanita mushrooms.CRC critical reviews in biochemistry · 1978
- Antamanide Prevents Bradykinin-lnduced Filamin Translocation by Inhibiting Extracellular Calcium Influx.Drug delivery · 1997
- Immunosuppressive activity of antamanide and some of its analogues.Peptides · 1992
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 1146.590238696
Show 4 more facts
- chemical formula
- C₆₄H₇₈N₁₀O₁₀
- subject has role
- antidote
- isomeric SMILES
- O=C2N9C(C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N6C(C(=O)N5[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H]2C(C)C)Cc3ccccc3)Cc4ccccc4)CCC5)CCC6)Cc7ccccc7)Cc8ccccc8)C)CCC9
- canonical SMILES
- CC1NC(=O)C2CCCN2C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccccc2)NC(=O)C2CCCN2C(=O)C2CCCN2C(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccccc2)NC1=O
Sources (1)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Biochemical properties
- Effect of altering the peptide structure on anti-phalloidin activity
- Inhibitor of mitochondrial permeability transition pore
- Synthesis of antamanide
- References
Antamanide is a cyclic decapeptide isolated from a fungus, the death cap: Amanita phalloides. It was being studied in 1995 as a potential anti-toxin against the effects of phalloidin and for its potential for treating edema. It contains 1 valine residue, 4 proline residues, 1 alanine residue, and 4 phenylalanine residues with a structure of c(Val-Pro-Pro-Ala-Phe-Phe-Pro-Pro-Phe-Phe). It was isolated by determining the source of the anti-phalloidin activity from a lipophillic extraction from the organism. It has been shown that antamanide can react to form alkali metal ion complexes. These include complexes with sodium and calcium ions. When these complexes are formed, the cyclopeptide structure undergoes a conformational change.
==Biochemical properties== Anantamide has been shown to make many different types of biochemical activity.
Excerpted from Wikipedia’s “antamanide” article, available under the CC BY-SA 4.0 licence.