β-Naphthoflavone

β-Naphthoflavone, also known as 5,6-benzoflavone, is a potent agonist of the aryl hydrocarbon receptor and as such is an inducer of such detoxification enzymes as cytochromes P450 (CYPs) and uridine 5'-diphospho-glucuronosyltransferases (UGTs).[1] β-Naphthoflavone is a putative chemopreventive agent.[2]

β-Naphthoflavone
Names
IUPAC name
Benzo[5,6]flavone
Systematic IUPAC name
3-Phenyl-1H-naphtho[2,1-b]pyran-1-one
Other names
5,6-Benzoflavone, BNF
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.025.417
UNII
  • InChI=1S/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H checkY
    Key: OUGIDAPQYNCXRA-UHFFFAOYSA-N checkY
  • InChI=1/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H
    Key: OUGIDAPQYNCXRA-UHFFFAOYAM
  • O=C\1c3c(O/C(=C/1)c2ccccc2)ccc4c3cccc4
Properties
C19H12O2
Molar mass 272.303 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

See also

References
  1. Chlouchi A, Girard C, Bonet A, Viollon-Abadie C, Heyd B, Mantion G, Martin H, Richert L (2007). "Effect of chrysin and natural coumarins on UGT1A1 and 1A6 activities in rat and human hepatocytes in primary culture". Planta Med. 73 (8): 742–7. doi:10.1055/s-2007-981548. PMID 17599282.
  2. Izzotti A, Bagnasco M, Cartiglia C, Longobardi M, Camoirano A, Tampa E, Lubet RA, De Flora S (2005). "Modulation of multigene expression and proteome profiles by chemopreventive agents". Mutat Res. 591 (1–2): 212–23. doi:10.1016/j.mrfmmm.2005.03.032. PMID 16083920.



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