3-O-Methylfunicone

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

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
CAS Number	28403-06-7 N[[1]]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3593571
ChemSpider	8723692
PubChem CID	10548301
CompTox Dashboard (EPA)	DTXSID801045493
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. "KNApSAcK Metabolite Information - C00038270". www.knapsackfamily.com.
2. 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.
3. 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. Bibcode:1999PChem..52.1399D. doi:10.1016/S0031-9422(99)00320-9.