Pederin

Pederin
Names
	IUPAC name (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
	Other names Pederine
Identifiers
CAS Number	27973-72-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78591 ;
ChemSpider	4529295 ;
PubChem CID	5381287;
UNII	B8F7J348GJ ;
CompTox Dashboard (EPA)	DTXSID90182248 ;
	InChI InChI=1S/C25H45NO9/c1-14-12-25(33-9,35-16(3)15(14)2)21(28)22(29)26-23(32-8)18-11-19(27)24(4,5)20(34-18)10-17(31-7)13-30-6/h15-21,23,27-28H,1,10-13H2,2-9H3,(H,26,29)/t15-,16-,17+,18+,19-,20-,21-,23+,25-/m1/s1 Key: ZNEZZONMADKYTB-VRCUBXEUSA-N ; InChI=1/C25H45NO9/c1-14-12-25(33-9,35-16(3)15(14)2)21(28)22(29)26-23(32-8)18-11-19(27)24(4,5)20(34-18)10-17(31-7)13-30-6/h15-21,23,27-28H,1,10-13H2,2-9H3,(H,26,29)/t15-,16-,17+,18+,19-,20-,21-,23+,25-/m1/s1 Key: ZNEZZONMADKYTB-VRCUBXEUBY;
	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;
Properties
Chemical formula	C25H45NO9
Molar mass	503.6261
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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).

It has been demonstrated that the production of pederin relies on the activities of an endosymbiont (Pseudomonas ssp.) within Paederus.

The manufacture of pederin is largely confined to adult female beetles—larvae and males only store pederin acquired maternally (i.e., through eggs) or by ingestion.