Vermistatin

Vermistatin
Names
	Preferred IUPAC name (3R)-4,6-Dimethoxy-3-{4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-yl}-2-benzofuran-1(3H)-one
	Other names 5-(4,6-Dimethoxyphthalidyl)-2-propenyl-4H-pyran-4-one
Identifiers
CAS Number	72669-21-7 ;
3D model (JSmol)	Interactive image ;
ChEMBL	ChEMBL1997854 ;
ChemSpider	4578500 ;
PubChem CID	5467588 ;
UNII	GX8U4VXD8W ;
CompTox Dashboard (EPA)	DTXSID001045463 ;
	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	328.320 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

Last updated August 02, 2025

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

↑ 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.
↑ 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. Bibcode:2012JNAtP..75..344S. doi:10.1021/np200414c. PMC 3330824 . PMID 22295871.

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[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.

[pmid22295871-2] 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. Bibcode:2012JNAtP..75..344S. doi:10.1021/np200414c. PMC 3330824 . PMID 22295871.

[1]

[2]

Names

Preferred IUPAC name (3R)-4,6-Dimethoxy-3-{4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-yl}-2-benzofuran-1(3H)-one
Other names 5-(4,6-Dimethoxyphthalidyl)-2-propenyl-4H-pyran-4-one
Identifiers
CAS Number	72669-21-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1997854
ChemSpider	4578500
PubChem CID	5467588
UNII	GX8U4VXD8W ^Y
CompTox Dashboard (EPA)	DTXSID001045463
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	328.320 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