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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 of 5,6-BENZOFLAVONE

SMILES

O=C1C=C(OC2=C1C3=C(C=CC=C3)C=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

PubMed

TitleDatePubMed
Enhancing effect of inducers of liver microsomal enzymes on induction of hyperplastic liver nodules by N-2-fluorenylacetamide in rats.
1979 Dec
Chiral metabolism of propafenone in rat hepatic microsomes treated with two inducers.
2001 Dec
Hepatic 7-ethoxyresorufin O-deethylase activity in eel (Anguilla anguilla) from the Thames Estuary and comparisons with other United Kingdom Estuaries.
2001 Dec
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
Evidence supporting the interaction of CYP2B4 and CYP1A2 in microsomal preparations.
2001 Dec
Induction by xenobiotics of phase I and phase II enzyme activities in the human keratinocyte cell line NCTC 2544.
2001 Dec
Estrogen-mediated suppression of cytochrome P4501A (CYP1A) expression in rainbow trout hepatocytes: role of estrogen receptor.
2001 Dec 21
Contribution of CYP1A2 in the hepatic metabolism of melatonin: studies with isolated microsomal preparations and liver slices.
2001 Nov
Regulation of rat carboxylesterase expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD): a dose-dependent decrease in mRNA levels but a biphasic change in protein levels and activity.
2001 Nov
A systematic gene expression screen of Caenorhabditis elegans cytochrome P450 genes reveals CYP35 as strongly xenobiotic inducible.
2001 Nov 15
An aryl hydrocarbon receptor (AHR) homologue from the soft-shell clam, Mya arenaria: evidence that invertebrate AHR homologues lack 2,3,7,8-tetrachlorodibenzo-p-dioxin and beta-naphthoflavone binding.
2001 Oct 31
Differences between rats and mice in induction of 4S beta-naphthoflavone-binding protein expression by treatment with beta-naphthoflavone.
2002
The zebrafish (Danio rerio) aryl hydrocarbon receptor type 1 is a novel vertebrate receptor.
2002 Aug
Gill filament-based EROD assay for monitoring waterborne dioxin-like pollutants in fish.
2002 Aug 1
DNA adduct formation from quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine as revealed by the 32P-postlabeling technique.
2002 Aug 15
Characterization of human CYP1A1/1A2 induction by DNA microarray and alpha-naphthoflavone.
2002 Aug 9
Cryopreserved precision-cut rat liver slices: morphology and cytochrome P450 isoforms expression after prolonged incubation.
2002 Dec
Juvenile sea bass liver P450, EROD induction, and erythrocytic genotoxic responses to PAH and PAH-like compounds.
2002 Feb
Effects of lactic acid bacteria on the uptake and distribution of the food mutagen Trp-P-2 in mice.
2002 Feb
Cytochrome P4501A responses in two tropical fish species, riverine catfish (Rita rita) and marine mudfish (Apocryptes bato).
2002 Jan
Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumor agent 2-(4-amino-3-methylphenyl) benzothiazole.
2002 Jan
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
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
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
Cytochrome P4501A (CYP1A) in killifish (Fundulus heteroclitus): heritability of altered expression and relationship to survival in contaminated sediments.
2002 Jul
Expression and inducibility of cytochrome P450 isoforms in 1-year-old intrasplenic liver cell transplants in rats.
2002 Mar
Expression of HSP70 and CYP1A protein in ovary and liver of juvenile rainbow trout exposed to beta-naphthoflavone.
2002 Mar
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
Glucuronidation of acetaminophen catalyzed by multiple rat phenol UDP-glucuronosyltransferases.
2002 Mar
The p23 co-chaperone facilitates dioxin receptor signaling in a yeast model system.
2002 Mar 24
Beta-naphthoflavone liver EROD and erythrocytic nuclear abnormality induction in juvenile Dicentrarchus labrax L.
2002 May
Liver phase I and phase II enzymatic induction and genotoxic responses of beta-naphthoflavone water-exposed sea bass.
2002 May
Tissue-specific regulation of canine intestinal and hepatic phenol and morphine UDP-glucuronosyltransferases by beta-naphthoflavone in comparison with humans.
2002 May 1
beta-naphthoflavone, an inducer of xenobiotic metabolizing enzymes, inhibits firefly luciferase activity.
2002 May 1
Calcium influx factor from cytochrome P-450 metabolism and secretion-like coupling mechanisms for capacitative calcium entry in corneal endothelial cells.
2002 May 10
In vivo and in vitro induction of cytochrome P450 enzymes in beagle dogs.
2002 Nov
Astaxanthin and canthaxanthin do not induce liver or kidney xenobiotic-metabolizing enzymes in rainbow trout (Oncorhynchus mykiss Walbaum).
2002 Nov
Effects of redox cycling compounds on glutathione content and activity of glutathione-related enzymes in rainbow trout liver.
2002 Nov
Diesel exhaust particle extracts and associated polycyclic aromatic hydrocarbons inhibit Cox-2-dependent prostaglandin synthesis in murine macrophages and fibroblasts.
2002 Oct 18
Naphthalene and beta-naphthoflavone effects on Anguilla anguilla L. hepatic metabolism and erythrocytic nuclear abnormalities.
2002 Sep
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
Altering cytochrome P4501A activity affects polycyclic aromatic hydrocarbon metabolism and toxicity in rainbow trout (Oncorhynchus mykiss).
2002 Sep
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.
2002 Sep 30
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
Induction of DNA strand breakage and apoptosis in the eel Anguilla anguilla.
2002 Sep-Dec
In vitro mechanistic differences in benzo[a]pyrene-DNA adduct formation using fish liver and mussel digestive gland microsomal activating systems.
2002 Sep-Dec
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
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
Quantitative PCR analysis of CYP1A induction in Atlantic salmon (Salmo salar).
2003 Jan 10
Human intestinal Caco-2 cells display active transport of benzo[a]pyrene metabolites.
2003 Jan 6
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:06:26 UTC 2023
Edited
by admin
on Thu Jul 06 00:06:26 UTC 2023
Record UNII
1BT0256Y8O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
5,6-BENZOFLAVONE
Common Name English
NSC-136015
Code 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
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
NCI_THESAURUS C54679
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
NCI_THESAURUS C54630
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
227-958-4
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID8030423
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
CHEBI
77013
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
FDA UNII
1BT0256Y8O
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
CAS
6051-87-2
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
NCI_THESAURUS
C29812
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY NCIT
PUBCHEM
2361
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
DRUG BANK
DB06732
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
WIKIPEDIA
beta-Naphthoflavone
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
NSC
136015
Created by admin on Thu Jul 06 00:06:26 UTC 2023 , Edited by admin on Thu Jul 06 00:06:26 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> ACTIVATOR
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ACTIVE MOIETY