5,6-BENZOFLAVONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H12O2
Molecular Weight	272.2974
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1C=C(OC2=C1C3=CC=CC=C3C=C2)C4=CC=CC=C4

InChI

InChIKey=OUGIDAPQYNCXRA-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H12O2
Molecular Weight	272.2974
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Enhancing effect of inducers of liver microsomal enzymes on induction of hyperplastic liver nodules by N-2-fluorenylacetamide in rats.	1979 Dec	117197
Chiral metabolism of propafenone in rat hepatic microsomes treated with two inducers.	2001 Dec	11854911
Hepatic 7-ethoxyresorufin O-deethylase activity in eel (Anguilla anguilla) from the Thames Estuary and comparisons with other United Kingdom Estuaries.	2001 Dec	11827118
Evaluation of 7-benzyloxy-4-trifluoromethylcoumarin, some other 7-hydroxy-4-trifluoromethylcoumarin derivatives and 7-benzyloxyquinoline as fluorescent substrates for rat hepatic cytochrome P450 enzymes.	2001 Dec	11780761
Evidence supporting the interaction of CYP2B4 and CYP1A2 in microsomal preparations.	2001 Dec	11717170
Comparison of activities dependent on glutathione S-transferase and cytochrome P-450 IA1 in cultured keratinocytes and reconstructed epidermal models.	2002	12476009
Differences between rats and mice in induction of 4S beta-naphthoflavone-binding protein expression by treatment with beta-naphthoflavone.	2002	12177527
The zebrafish (Danio rerio) aryl hydrocarbon receptor type 1 is a novel vertebrate receptor.	2002 Aug	12130674
Gill filament-based EROD assay for monitoring waterborne dioxin-like pollutants in fish.	2002 Aug 1	12188363
DNA adduct formation from quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine as revealed by the 32P-postlabeling technique.	2002 Aug 15	12204579
Characterization of human CYP1A1/1A2 induction by DNA microarray and alpha-naphthoflavone.	2002 Aug 9	12147246
Characterization and identification of cytochrome P450 metabolites of arachidonic acid released by human peritoneal macrophages obtained from the pouch of Douglas.	2002 Dec	12468260
Complementary DNA cloning, sequence analysis and differential organ expression of beta-naphthoflavone-inducible cytochrome P4501A in Atlantic salmon (Salmo salar).	2002 Dec	12458189
Cryopreserved precision-cut rat liver slices: morphology and cytochrome P450 isoforms expression after prolonged incubation.	2002 Dec	12423659
Juvenile sea bass liver P450, EROD induction, and erythrocytic genotoxic responses to PAH and PAH-like compounds.	2002 Feb	11886185
Effects of lactic acid bacteria on the uptake and distribution of the food mutagen Trp-P-2 in mice.	2002 Feb	11843060
Cytochrome P4501A responses in two tropical fish species, riverine catfish (Rita rita) and marine mudfish (Apocryptes bato).	2002 Jan	11796326
Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumor agent 2-(4-amino-3-methylphenyl) benzothiazole.	2002 Jan	11752201
Organ distribution of multidrug resistance proteins 1, 2, and 3 (Mrp1, 2, and 3) mRNA and hepatic induction of Mrp3 by constitutive androstane receptor activators in rats.	2002 Jan	11752103
CYP1A-mediated metabolism of the Janus kinase-3 inhibitor 4-(4'-hydroxyphenyl)-amino-6,7-dimethoxyquinazoline: structural basis for inactivation by regioselective O-demethylation.	2002 Jan	11744615
Influence of t-butylhydroquinone and beta-naphthoflavone on formation and transport of 4-methylumbelliferone glucuronide in Caco-2/TC-7 cell monolayers.	2002 Jan 15	11841785
Cytochrome P4501A (CYP1A) in killifish (Fundulus heteroclitus): heritability of altered expression and relationship to survival in contaminated sediments.	2002 Jul	12075112
Expression and inducibility of cytochrome P450 isoforms in 1-year-old intrasplenic liver cell transplants in rats.	2002 Mar	11935166
Expression of HSP70 and CYP1A protein in ovary and liver of juvenile rainbow trout exposed to beta-naphthoflavone.	2002 Mar	11912063
Identification of a new mutagenic polychlorinated biphenyl derivative in the Waka River, Wakayama, Japan, showing activation of an aryl hydrocarbon receptor-dependent transcription.	2002 Mar	11896690
Glucuronidation of acetaminophen catalyzed by multiple rat phenol UDP-glucuronosyltransferases.	2002 Mar	11854153
The p23 co-chaperone facilitates dioxin receptor signaling in a yeast model system.	2002 Mar 24	11879970
Beta-naphthoflavone liver EROD and erythrocytic nuclear abnormality induction in juvenile Dicentrarchus labrax L.	2002 May	12051810
Liver phase I and phase II enzymatic induction and genotoxic responses of beta-naphthoflavone water-exposed sea bass.	2002 May	12051809
Tissue-specific regulation of canine intestinal and hepatic phenol and morphine UDP-glucuronosyltransferases by beta-naphthoflavone in comparison with humans.	2002 May 1	12007571
beta-naphthoflavone, an inducer of xenobiotic metabolizing enzymes, inhibits firefly luciferase activity.	2002 May 1	11969196
Calcium influx factor from cytochrome P-450 metabolism and secretion-like coupling mechanisms for capacitative calcium entry in corneal endothelial cells.	2002 May 10	11867616
In vivo and in vitro induction of cytochrome P450 enzymes in beagle dogs.	2002 Nov	12386126
Astaxanthin and canthaxanthin do not induce liver or kidney xenobiotic-metabolizing enzymes in rainbow trout (Oncorhynchus mykiss Walbaum).	2002 Nov	12379428
Effects of redox cycling compounds on glutathione content and activity of glutathione-related enzymes in rainbow trout liver.	2002 Nov	12379427
Diesel exhaust particle extracts and associated polycyclic aromatic hydrocarbons inhibit Cox-2-dependent prostaglandin synthesis in murine macrophages and fibroblasts.	2002 Oct 18	12163478
Benzo[a]pyrene and beta-naphthoflavone mutagenic activation by European eel (Anguilla anguilla L.) S9 liver fraction.	2002 Sep	12481862
Naphthalene and beta-naphthoflavone effects on Anguilla anguilla L. hepatic metabolism and erythrocytic nuclear abnormalities.	2002 Sep	12220115
2,3,7,8-tetrachlorodibenzo-p-dioxin toxicity in the zebrafish embryo: local circulation failure in the dorsal midbrain is associated with increased apoptosis.	2002 Sep	12215674
Altering cytochrome P4501A activity affects polycyclic aromatic hydrocarbon metabolism and toxicity in rainbow trout (Oncorhynchus mykiss).	2002 Sep	12206424
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.	2002 Sep 30	12351144
The expression of CYP1A, vitellogenin and zona radiata proteins in Atlantic salmon (Salmo salar) after oral dosing with two commercial PBDE flame retardant mixtures: absence of short-term responses.	2002 Sep-Dec	12408642
Induction of DNA strand breakage and apoptosis in the eel Anguilla anguilla.	2002 Sep-Dec	12408611
In vitro mechanistic differences in benzo[a]pyrene-DNA adduct formation using fish liver and mussel digestive gland microsomal activating systems.	2002 Sep-Dec	12408608
Increased protein stability as a mechanism that enhances Nrf2-mediated transcriptional activation of the antioxidant response element. Degradation of Nrf2 by the 26 S proteasome.	2003 Feb 14	12446695
The presence of inducible cytochrome P450 types 1A1 and 1A2 in the BeWo cell line.	2003 Jan	12495659
Preclinical factors influencing the relative contributions of Phase I and II enzymes to the metabolism of the experimental anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid.	2003 Jan 1	12473385
Quantitative PCR analysis of CYP1A induction in Atlantic salmon (Salmo salar).	2003 Jan 10	12413795
Nrf2 mediates the induction of ferritin H in response to xenobiotics and cancer chemopreventive dithiolethiones.	2003 Jan 24	12435735
Human intestinal Caco-2 cells display active transport of benzo[a]pyrene metabolites.	2003 Jan 6	12453661

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:34:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:34:31 GMT 2025`
Record UNII	1BT0256Y8O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5,6-BENZOFLAVONE

Common Name

English

NSC-136015

Preferred Name

English

BETA-NAPHTHOFLAVONE

Common Name

English

BNF

Common Name

English

1H-NAPHTHO(2,1-B)PYRAN-1-ONE, 3-PHENYL-

Systematic Name

English

.BETA.-NAPHTHOFLAVONE

Common Name

English

BENZOFLAVONE, 5,6-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C54629