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β-Naphthoflavone

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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
CAS Number	6051-87-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:77013^N
ChEMBL	ChEMBL26260^Y
ChemSpider	2271^Y
DrugBank	DB06732^Y
ECHA InfoCard	100.025.417
PubChem CID	2361
UNII	1BT0256Y8O^Y
CompTox Dashboard(EPA)	DTXSID8030423
InChI 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^Y Key: OUGIDAPQYNCXRA-UHFFFAOYSA-N^Y 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
SMILES O=C\1c3c(O/C(=C/1)c2ccccc2)ccc4c3cccc4
Properties
Chemical formula	C₁₉H₁₂O₂
Molar mass	272.303 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

β-Naphthoflavone, also known as5,6-benzoflavone, is a potent agonist of thearyl hydrocarbon receptor and as such is an inducer of suchdetoxification enzymes ascytochromes P450 (CYPs) anduridine 5'-diphospho-glucuronosyltransferases (UGTs).^[1] β-Naphthoflavone is a putativechemopreventive agent.^[2]

^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.S2CID 260281088.
^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.

v t e Aryl hydrocarbon receptor modulators
AhRTooltip Aryl hydrocarbon receptor	Agonists:Arachidonic acid metabolites (e.g.,lipoxin A4,prostaglandin G2) Dietary carotenoids Flutamide Halogenated aromatic hydrocarbons (e.g.,polychlorinated dibenzodioxins (e.g.,TCDD),dibenzofurans,biphenyls) ΙΤΕ Modified low-density lipoproteins Polycyclic aromatic hydrocarbons (e.g.,3-methylcholanthrene,benzo[a]pyrene,benzanthracenes,benzoflavones (e.g.,β-naphthoflavone)) Tapinarof (benvitimod) Tetrapyrroles (e.g.,bilirubin) Tryptophan derivatives (e.g.,indigo dye,indirubin) Antagonists:7-Ketocholesterol CH-223191 Cyproterone acetate
See also Receptor/signaling modulators

AhRTooltip Aryl hydrocarbon receptor