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Vermistatin

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Vermistatin
Names
IUPAC name
(3R)-4,6-Dimethoxy-3-[4-oxo-6-[(E)-prop-1-enyl]pyran-3-yl]-3H-2-benzofuran-1-one
Other names
5-(4,6-Dimethoxyphthalidyl)-2-propenyl-4H-pyran-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C18H16O6/c1-4-5-10-7-14(19)13(9-23-10)17-16-12(18(20)24-17)6-11(21-2)8-15(16)22-3/h4-9,17H,1-3H3/b5-4+/t17-/m0/s1
    Key: YORFGPDHNOBVBM-BDUNBXCCSA-N
  • InChI=1/C18H16O6/c1-4-5-10-7-14(19)13(9-23-10)17-16-12(18(20)24-17)6-11(21-2)8-15(16)22-3/h4-9,17H,1-3H3/b5-4+/t17-/m0/s1
    Key: YORFGPDHNOBVBM-BDUNBXCCBS
  • C/C=C/C1=CC(=O)C(=CO1)[C@H]2C3=C(C=C(C=C3C(=O)O2)OC)OC
Properties
C18H16O6
Molar mass 328.320 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vermistatin is an organic compound and a metabolite of mine-dwelling Penicillium vermiculatum found in Berkeley Pit Lake, Butte, Montana.[1] Penisimplicissin is a vermistatin analog with anticancer activity.[2]

References

  1. ^ Fuska, J; Uhrín, D; Proksa, B; Votický, Z; Ruppeldt, J (1986). "The structure of vermistatin, a new metabolite from Penicillium vermiculatum". The Journal of Antibiotics. 39 (11): 1605–8. doi:10.7164/antibiotics.39.1605. PMID 3793630.
  2. ^ Stierle AA, Stierle DB, Girtsman T (2012). "Caspase-1 inhibitors from an extremophilic fungus that target specific leukemia cell lines". J Nat Prod. 75 (3): 344–50. doi:10.1021/np200414c. PMC 3330824. PMID 22295871.


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