Vermistatin

Vermistatin
Names
	Preferred IUPAC name (3R)-4,6-Dimethoxy-3-{4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-yl
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

-2-benzofuran-1(3H)-one

| OtherNames = 5-(4,6-Dimethoxyphthalidyl)-2-propenyl-4H-pyran-4-one | Section1 = ! colspan=2 style="background: #f8eaba;color:inherit; text-align: center;" |Identifiers

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CAS Number

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72669-21-7

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3D model (JSmol)

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Interactive image

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| ChEMBL

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ChEMBL1997854

|- | ChemSpider

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4578500

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PubChem CID

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5467588

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| UNII

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GX8U4VXD8W^Y

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CompTox Dashboard (EPA)

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DTXSID001045463

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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

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SMILES

C/C=C/C1=CC(=O)C(=CO1)[C@H]2C3=C(C=C(C=C3C(=O)O2)OC)OC

|- | Section2 = ! colspan=2 style="background: #f8eaba;color:inherit; text-align: center;" |Properties

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Chemical formula

| C₁₈H₁₆O₆

|- | Molar mass

| 328.320 g·mol⁻¹

|- | Section3 = }}

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. 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. doi:10.1021/np200414c. PMC 3330824. PMID 22295871.

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[2]