3-O-Methylfunicone

3-O-Methylfunicone is a chemical compound isolated from Penicillium pinophilum.[1] It inhibits the growth of phytopathogenic fungi.[2]

3-O-Methylfunicone
Names
Preferred IUPAC name
Methyl 3,5-dimethoxy-2-{5-methoxy-4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-carbonyl}benzoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
InChI
  • InChI=1S/C20H20O8/c1-6-7-14-19(26-4)18(22)13(10-28-14)17(21)16-12(20(23)27-5)8-11(24-2)9-15(16)25-3/h6-10H,1-5H3/b7-6+
    Key: WGLRJONCGNNMKL-VOTSOKGWSA-N
  • InChI=1/C20H20O8/c1-6-7-14-19(26-4)18(22)13(10-28-14)17(21)16-12(20(23)27-5)8-11(24-2)9-15(16)25-3/h6-10H,1-5H3/b7-6+
    Key: WGLRJONCGNNMKL-VOTSOKGWBV
SMILES
  • C/C=C/c1c(c(=O)c(co1)C(=O)c2c(cc(cc2OC)OC)C(=O)OC)OC
Properties
Chemical formula
 C20H20O8
Molar mass 388.368 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Buommino, E; Tirino, V; De Filippis, A; Silvestri, F; Nicoletti, R; Ciavatta, ML; Pirozzi, G; Tufano, MA (2011). "3-O-methylfunicone, from Penicillium pinophilum, is a selective inhibitor of breast cancer stem cells". Cell Proliferation. 44 (5): 401–9. doi:10.1111/j.1365-2184.2011.00766.x. PMC 6495666. PMID 21951283.
  2. De Stefano, Salvatore; Nicoletti, Rosario; Milone, Alfredo; Zambardino, Salvatore (December 1999). "3-o-Methylfunicone, a fungitoxic metabolite produced by the fungus Penicillium pinophilum". Phytochemistry. 52 (8): 1399–1401. doi:10.1016/S0031-9422(99)00320-9.
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