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Antamanide information


Antamanide
Identifiers
CAS Number
  • 16898-32-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2300791 checkY
ECHA InfoCard 100.037.203 Edit this at Wikidata
PubChem CID
  • 9876840
CompTox Dashboard (EPA)
  • DTXSID80903964 Edit this at Wikidata
InChI
  • InChI=1S/C64H78N10O10/c1-40(2)54-64(84)74-35-19-31-53(74)63(83)71-32-16-28-50(71)59(79)65-41(3)55(75)66-46(36-42-20-8-4-9-21-42)57(77)69-49(39-45-26-14-7-15-27-45)61(81)73-34-18-30-52(73)62(82)72-33-17-29-51(72)60(80)68-47(37-43-22-10-5-11-23-43)56(76)67-48(58(78)70-54)38-44-24-12-6-13-25-44/h4-15,20-27,40-41,46-54H,16-19,28-39H2,1-3H3,(H,65,79)(H,66,75)(H,67,76)(H,68,80)(H,69,77)(H,70,78)/t41-,46-,47-,48-,49-,50-,51-,52-,53-,54-/m0/s1 ☒N
    Key: WTINJQXJTHUFRF-IHTIUHOMSA-N ☒N
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)Cc6ccccc6)Cc7ccccc7)Cc8ccccc8)Cc9ccccc9
Properties
Chemical formula
C64H78N10O10
Molar mass 1147.36 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Antamanide is a cyclic decapeptide isolated from a fungus, the death cap: Amanita phalloides.[1] It is being studied as a potential anti-toxin against the effects of phalloidin and for its potential for treating edema.[2] 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.[1]

  1. ^ a b Wieland T, Faulstich H (1978). "Amatoxins, phallotoxins, phallolysin, and antamanide: the biologically active components of poisonous Amanita mushrooms". CRC Crit. Rev. Biochem. 5 (3): 185–260. doi:10.3109/10409237809149870. PMID 363352.
  2. ^ David Shepro and J. Steven Alexander, Prophylactic and therapeutic methods for treating edema with antamanides. United States Patent 5466667.

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Antamanide

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Antamanide is a cyclic decapeptide isolated from a fungus, the death cap: Amanita phalloides. It is being studied as a potential anti-toxin against the...

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Amanita phalloides

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(red blood cell–destroying) activity in vitro. An unrelated compound, antamanide, has also been isolated. Amatoxins consist of at least eight compounds...

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Phallolysin

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phalloides Amanita Hemolysis Phallotoxin Amatoxin Virotoxins Phalloidin Antamanide Faulstich H, Bühring HJ, Seitz J (September 1983). "Physical properties...

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Amanullinic acid

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Wieland; Faulstich H. (1978). "Amatoxins, Phallotoxins, Phallolysin, and Antamanide: the Biologically Active Components of Poisonous Amanita Mushrooms". CRC...

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