Pederin

Pederin

Names
IUPAC name (2S)-N-[(S)-[(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyl-2-tetrahydropyranyl]-methoxymethyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-2-tetrahydropyranyl]acetamide
Other names Pederine
Identifiers
CAS Number	27973-72-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:78591 N
ChemSpider	4529295 N
PubChem	5381287
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 N Key: ZNEZZONMADKYTB-VRCUBXEUSA-N 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).
N  (what is YN ?)
Infobox references

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

Pederin blocks mitosis at levels as low as 1 ng/ml, by inhibiting protein and DNA synthesis without affecting RNA synthesis, prevents cell division, and has been shown to extend the life of mice bearing a variety of tumors.<missing reference> For these reasons, it has garnered interest as a potential anti-cancer treatment.