Vermistatin

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 (Jmol)	Interactive image
ChEMBL	ChEMBL1997854
ChemSpider	4578500
PubChem	5467588
InChI 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
SMILES C/C=C/C1=CC(=O)C(=CO1)[C@H]2C3=C(C=C(C=C3C(=O)O2)OC)OC
Properties
Chemical formula	C18H16O6
Molar mass	328.32 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

Vermistatin is a bio-active metabolite of mine-dwelling Penicillium vermiculatum (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.