β-Naphthoflavone - Misplaced Pages

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β-Naphthoflavone
Names

IUPAC name Benzoflavone
Systematic IUPAC name 3-Phenyl-1H-naphthopyran-1-one
Other names 5,6-Benzoflavone, BNF
Identifiers
CAS Number	6051-87-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:77013
ChEMBL	ChEMBL26260
ChemSpider	2271
DrugBank	DB06732
ECHA InfoCard	100.025.417
PubChem CID	2361
UNII	1BT0256Y8O
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/h1-12HKey: OUGIDAPQYNCXRA-UHFFFAOYSA-N 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/h1-12HKey: OUGIDAPQYNCXRA-UHFFFAOYAM
SMILES O=C\1c3c(O/C(=C/1)c2ccccc2)ccc4c3cccc4
Properties
Chemical formula	C₁₉H₁₂O₂
Molar mass	272.303 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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). β-Naphthoflavone is a putative chemopreventive agent.

References

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, benzopyrene, 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

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