Pterulone

Pterulone
Names
Preferred IUPAC name
1-[(3Z)-3-(Chloromethylidene)-2,3-dihydro-1-benzoxepin-7-yl]ethan-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7- checkY
    Key: QEWSARCWWQPUSM-YFHOEESVSA-N checkY
  • InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7-
  • InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7-
    Key: QEWSARCWWQPUSM-YFHOEESVSA-N
  • O=C(c2ccc1OCC(/C=C\c1c2)=[C@H]Cl)C
Properties
C13H11ClO2
Molar mass 234.678
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pterulone is a fungal metabolite. It was initially isolated from the mycelium and liquid cultures of wood-decay fungus in the genus Pterula. The compound inhibits eukaryotic respiration by targeting the mitochondrial NADH:ubiquinone oxidoreductase.

References

  1. ↑ Engler M, Anke T, Sterner O, Brandt U (1997). "Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. I. Production, isolation and biological activities". Journal of Antibiotics. 50 (4): 325–9. doi:10.7164/antibiotics.50.325. PMID 9186558.