Collybolide

Collybolide
Names
Systematic IUPAC name
(3S,4R,4aS,5R,8R,9aR)-4-(benzoyloxy)-3-(3-furanyl)hexahydro-5-methyl-5,8-Methano-1H-pyrano[3,4-d]oxepin-1,6(5H)-dione
Other names
  • (+)-Collybolide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C22H20O7/c1-22-10-14(27-21(22)25)9-15-16(22)18(29-19(23)12-5-3-2-4-6-12)17(28-20(15)24)13-7-8-26-11-13/h2-8,11,14-18H,9-10H2,1H3/t14-,15-,16-,17+,18-,22-/m1/s1
    Key: JLFUOYRQSZADHD-NVKOURDFSA-N
  • InChI=1S/C22H20O7/c1-22-10-14(27-21(22)25)9-15-16(22)18(29-19(23)12-5-3-2-4-6-12)17(28-20(15)24)13-7-8-26-11-13/h2-8,11,14-18H,9-10H2,1H3
    Key: JLFUOYRQSZADHD-UHFFFAOYSA-N
  • O(C(=O)C1=CC=CC=C1)[C@@H]2[C@@]3([C@@]4(C)C[C@@H](C[C@]3(C(=O)O[C@]2(C=5C=COC5)[H])[H])OC4=O)[H]
  • CC12CC(C(C3C1C(C(OC3=O)C4=COC=C4)OC(=O)C5=CC=CC=C5))OC2=O
Properties
C22H20O7
Molar mass 396.395 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Collybolide is a secondary metabolite of the Rhodocollybia maculata mushroom, a basidiomycete fungus that grows on rotting conifer wood. It was previously believed to be a potent and selective kappa-opioid receptor agonist. However, a total synthesis and independent biological assay determined that collybolide neither excites nor suppresses kappa-opioid receptor signaling. Collybolide is unlikely to be psychoactive, although it has been shown to inhibit L-type calcium channels in isolated rat aorta.

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