pederin

Also known as paederine, pederine, (+)-pederin, (+)-pederine

Pederin is a vesicant toxic amide with two tetrahydropyran rings, found in the haemolymph of the beetle genus Paederus, including the Nairobi fly, belonging to the family Staphylinidae. It was first characterized by processing 25 million field-collected P. fuscipes. It makes up approximately 0.025% of an insect's weight (for P. fuscipes).

Chemical data

Formula: C25H45NO9
Molecular weight: 503.6 g/mol
IUPAC name: (2S)-N-[(S)-[(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyloxan-2-yl]-methoxymethyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide
SMILES: C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@H]([C@@H]2C[C@H](C([C@H](O2)C[C@@H](COC)OC)(C)C)O)OC)O)OC)C
InChIKey: ZNEZZONMADKYTB-VRCUBXEUSA-N
XLogP: 1
Polar surface area: 125 Å²
H-bond donors: 3
H-bond acceptors: 9
Formal charge: 0

via PubChem

Wikidata facts

Has part: carbon
Mass: 503.309

Show 4 more facts

chemical formula: C₂₅H₄₅NO₉
canonical SMILES: CC1C(OC(CC1=C)(C(C(=O)NC(C2CC(C(C(O2)CC(COC)OC)(C)C)O)OC)O)OC)C
isomeric SMILES: C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@H]([C@@H]2C[C@H](C([C@H](O2)C[C@@H](COC)OC)(C)C)O)OC)O)OC)C
found in taxon: Pseudomonas aeruginosa

Sources (3)

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Encyclopedic overview

6 sections

Contents

Physical effects
Synthesis
Mode of action
Uses
See also
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 411084531 | ImageFile=Pederin.png | ImageSize=200px | IUPACName= (2S)-N-[(S)-{(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyloxan-2-yl}(methoxy)methyl]-2-hydroxy-2-[(2S,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide | OtherNames=Pederine |Section1= |Section2= |Section3= }}

Excerpted from Wikipedia’s “pederin” article, available under the CC BY-SA 4.0 licence.