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
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.	2003-02-14	12446695
Nrf2 mediates the induction of ferritin H in response to xenobiotics and cancer chemopreventive dithiolethiones.	2003-01-24	12435735
Quantitative PCR analysis of CYP1A induction in Atlantic salmon (Salmo salar).	2003-01-10	12413795
Human intestinal Caco-2 cells display active transport of benzo[a]pyrene metabolites.	2003-01-06	12453661
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.	2003-01-01	12473385
The presence of inducible cytochrome P450 types 1A1 and 1A2 in the BeWo cell line.	2003-01	12495659
Characterization and identification of cytochrome P450 metabolites of arachidonic acid released by human peritoneal macrophages obtained from the pouch of Douglas.	2002-12	12468260
Complementary DNA cloning, sequence analysis and differential organ expression of beta-naphthoflavone-inducible cytochrome P4501A in Atlantic salmon (Salmo salar).	2002-12	12458189
Cryopreserved precision-cut rat liver slices: morphology and cytochrome P450 isoforms expression after prolonged incubation.	2002-12	12423659
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.	2002-11-01	12408642
Induction of DNA strand breakage and apoptosis in the eel Anguilla anguilla.	2002-11-01	12408611
In vitro mechanistic differences in benzo[a]pyrene-DNA adduct formation using fish liver and mussel digestive gland microsomal activating systems.	2002-11-01	12408608
In vivo and in vitro induction of cytochrome P450 enzymes in beagle dogs.	2002-11	12386126
Astaxanthin and canthaxanthin do not induce liver or kidney xenobiotic-metabolizing enzymes in rainbow trout (Oncorhynchus mykiss Walbaum).	2002-11	12379428
Effects of redox cycling compounds on glutathione content and activity of glutathione-related enzymes in rainbow trout liver.	2002-11	12379427
Diesel exhaust particle extracts and associated polycyclic aromatic hydrocarbons inhibit Cox-2-dependent prostaglandin synthesis in murine macrophages and fibroblasts.	2002-10-18	12163478
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.	2002-09-30	12351144
Benzo[a]pyrene and beta-naphthoflavone mutagenic activation by European eel (Anguilla anguilla L.) S9 liver fraction.	2002-09	12481862
Naphthalene and beta-naphthoflavone effects on Anguilla anguilla L. hepatic metabolism and erythrocytic nuclear abnormalities.	2002-09	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.	2002-09	12215674
Altering cytochrome P4501A activity affects polycyclic aromatic hydrocarbon metabolism and toxicity in rainbow trout (Oncorhynchus mykiss).	2002-09	12206424
DNA adduct formation from quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine as revealed by the 32P-postlabeling technique.	2002-08-15	12204579
Characterization of human CYP1A1/1A2 induction by DNA microarray and alpha-naphthoflavone.	2002-08-09	12147246
Gill filament-based EROD assay for monitoring waterborne dioxin-like pollutants in fish.	2002-08-01	12188363
The zebrafish (Danio rerio) aryl hydrocarbon receptor type 1 is a novel vertebrate receptor.	2002-08	12130674
Cytochrome P4501A (CYP1A) in killifish (Fundulus heteroclitus): heritability of altered expression and relationship to survival in contaminated sediments.	2002-07	12075112
Calcium influx factor from cytochrome P-450 metabolism and secretion-like coupling mechanisms for capacitative calcium entry in corneal endothelial cells.	2002-05-10	11867616
Tissue-specific regulation of canine intestinal and hepatic phenol and morphine UDP-glucuronosyltransferases by beta-naphthoflavone in comparison with humans.	2002-05-01	12007571
beta-naphthoflavone, an inducer of xenobiotic metabolizing enzymes, inhibits firefly luciferase activity.	2002-05-01	11969196
Beta-naphthoflavone liver EROD and erythrocytic nuclear abnormality induction in juvenile Dicentrarchus labrax L.	2002-05	12051810
Liver phase I and phase II enzymatic induction and genotoxic responses of beta-naphthoflavone water-exposed sea bass.	2002-05	12051809
The p23 co-chaperone facilitates dioxin receptor signaling in a yeast model system.	2002-03-24	11879970
Expression and inducibility of cytochrome P450 isoforms in 1-year-old intrasplenic liver cell transplants in rats.	2002-03	11935166
Expression of HSP70 and CYP1A protein in ovary and liver of juvenile rainbow trout exposed to beta-naphthoflavone.	2002-03	11912063
Identification of a new mutagenic polychlorinated biphenyl derivative in the Waka River, Wakayama, Japan, showing activation of an aryl hydrocarbon receptor-dependent transcription.	2002-03	11896690
Glucuronidation of acetaminophen catalyzed by multiple rat phenol UDP-glucuronosyltransferases.	2002-03	11854153
Juvenile sea bass liver P450, EROD induction, and erythrocytic genotoxic responses to PAH and PAH-like compounds.	2002-02	11886185
Effects of lactic acid bacteria on the uptake and distribution of the food mutagen Trp-P-2 in mice.	2002-02	11843060
Influence of t-butylhydroquinone and beta-naphthoflavone on formation and transport of 4-methylumbelliferone glucuronide in Caco-2/TC-7 cell monolayers.	2002-01-15	11841785
Cytochrome P4501A responses in two tropical fish species, riverine catfish (Rita rita) and marine mudfish (Apocryptes bato).	2002-01	11796326
Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumor agent 2-(4-amino-3-methylphenyl) benzothiazole.	2002-01	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.	2002-01	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.	2002-01	11744615
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
Chiral metabolism of propafenone in rat hepatic microsomes treated with two inducers.	2001-12	11854911
Hepatic 7-ethoxyresorufin O-deethylase activity in eel (Anguilla anguilla) from the Thames Estuary and comparisons with other United Kingdom Estuaries.	2001-12	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.	2001-12	11780761
Evidence supporting the interaction of CYP2B4 and CYP1A2 in microsomal preparations.	2001-12	11717170
Enhancing effect of inducers of liver microsomal enzymes on induction of hyperplastic liver nodules by N-2-fluorenylacetamide in rats.	1979-12	117197

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