Detail Information of Xenobiotics

General Information of Xenobiotics (ID: XEO01220)
Xenobiotics Name
Beta-naphthoflavone
Xenobiotics Type
Pharmaceutical Agent(s)
Classification
Investigative Agent
Structure
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3D MOL 2D MOL
PubChem CID
2361
DME(s) Modulated by This Xenobiotics
DME(s) Inhibited by This Xenobiotics
Aldo-keto reductase 1D1 (AKR1D1) DME Info Homo sapiens [1]
Aminomuconic semialdehyde dehydrogenase (ALDH12) DME Info Homo sapiens [1]
Cytochrome P450 1A1 (CYP1A1) DME Info Homo sapiens [2]
Cytochrome P450 1A2 (CYP1A2) DME Info Homo sapiens [2]
Cytochrome P450 1B1 (CYP1B1) DME Info Homo sapiens [3], [4]
Cytochrome P450 2C18 (CYP2C18) DME Info Homo sapiens [5]
Mephenytoin 4-hydroxylase (CYP2C19) DME Info Homo sapiens [5]
Cytochrome P450 2C9 (CYP2C9) DME Info Homo sapiens [5]
Cytochrome P450 2D6 (CYP2D6) DME Info Homo sapiens [6]
Cytochrome P450 3A4 (CYP3A4) DME Info Homo sapiens [6]
Cytochrome P450 3A7 (CYP3A7) DME Info Homo sapiens [6]
Cytochrome P450 4B1 (CYP4B1) DME Info Homo sapiens [6], [5]
Dimethylaniline oxidase 1 (FMO1) DME Info Homo sapiens [6]
Glutathione S-transferase alpha-1 (GSTA1) DME Info Homo sapiens [7]
HMG-CoA reductase (HMGCR) DME Info Homo sapiens [8], [9]
Keto-steroid reductase (HSD17B7) DME Info Homo sapiens [8]
Mevalonate pyrophosphate decarboxylase (MPD) DME Info Homo sapiens [9]
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME Info Homo sapiens [1]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME Info Homo sapiens [6]
DME(s) Induced by This Xenobiotics
Aldo-keto reductase 1A1 (AKR1A1) DME Info Homo sapiens [10]
Aldo-keto reductase 1C1 (AKR1C1) DME Info Homo sapiens [11]
Aldo-keto reductase 1C3 (AKR1C3) DME Info Homo sapiens [1]
Arachidonate 5-lipoxygenase (ALOX5) DME Info Homo sapiens [1]
Asparagine synthetase (ASNS) DME Info Homo sapiens [12]
NADPH-dependent carbonyl reductase 1 (CBR1) DME Info Homo sapiens [13], [1]
Steroid 11-beta-hydroxylase (CYP11B1) DME Info Homo sapiens [14]
Aromatase (CYP19A1) DME Info Homo sapiens [1]
Cytochrome P450 2A13 (CYP2A13) DME Info Homo sapiens [6]
Cytochrome P450 2A6 (CYP2A6) DME Info Homo sapiens [15]
Cytochrome P450 2B6 (CYP2B6) DME Info Homo sapiens [16], [6]
Cytochrome P450 2E1 (CYP2E1) DME Info Homo sapiens [17]
Leukotriene B4 omega-hydroxylase (CYP4F3) DME Info Homo sapiens [18]
Glutathione S-transferase pi (GSTP1) DME Info Homo sapiens [19]
Quinone reductase 1 (NQO1) DME Info Homo sapiens [19]
Sulfotransferase 1E1 (SULT1E1) DME Info Homo sapiens [6]
Thioredoxin reductase TR1 (TXNRD1) DME Info Homo sapiens [20], [1]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME Info Homo sapiens [21]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME Info Homo sapiens [15], [18]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME Info Homo sapiens [15], [18]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME Info Homo sapiens [15]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME Info Homo sapiens [18]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME Info Homo sapiens [15], [18]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME Info Homo sapiens [15], [18]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME Info Homo sapiens [22], [15]
Xenobiotics-DME Activity Data
Xenobiotics-DME Activity Data Cytochrome P450 1A1 (CYP1A1) DME Info IC50 = 0.054 microM [2]
Cytochrome P450 1A2 (CYP1A2) DME Info IC50 = 0.47 microM [2]
References
1 Identification of AhR-regulated genes involved in PAH-induced immunotoxicity using a highly-sensitive DNA chip, 3D-Gene human immunity and metabolic syndrome 9k. Toxicol In Vitro. 2010 Feb;24(1):85-91.
2 Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1. J Med Chem. 2013 May 23;56(10):4082-92.
3 Reverse type I binding spectra of human cytochrome P450 1B1 induced by flavonoid, stilbene, pyrene, naphthalene, phenanthrene, and biphenyl derivatives that inhibit catalytic activity: a structure-function relationship study. Chem Res Toxicol. 2009 Jul;22(7):1325-33.
4 Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010 Dec 20;23(12):1921-35.
5 Differentiation-specific factors modulate epidermal CYP1-4 gene expression in human skin in response to retinoic acid and classic aryl hydrocarbon receptor ligands. J Pharmacol Exp Ther. 2006 Dec;319(3):1162-71.
6 Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins. Cell Biol Toxicol. 2012 Apr;28(2):69-87.
7 Diversified expression of aryl hydrocarbon receptor dependent genes in human laryngeal squamous cell carcinoma cell lines treated with beta-naphthoflavone. Toxicol Lett. 2014 Nov 18;231(1):99-107.
8 Aryl hydrocarbon receptor regulates the cholesterol biosynthetic pathway in a dioxin response element-independent manner. Hepatology. 2012 Jun;55(6):1994-2004.
9 Selective Ah receptor ligands mediate enhanced SREBP1 proteolysis to restrict lipogenesis in sebocytes. Toxicol Sci. 2019 Jun 21;171(1):146-158.
10 Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res. 1999 Feb 1;59(3):607-14.
11 Metabolic enzyme induction by HepG2 cells exposed to oxygenated and nonoxygenated polycyclic aromatic hydrocarbons. Chem Res Toxicol. 2007 Feb;20(2):277-83.
12 Determination of phospholipidosis potential based on gene expression analysis in HepG2 cells. Toxicol Sci. 2007 Mar;96(1):101-14.
13 Functional characterization of the promoter of human carbonyl reductase 1 (CBR1)Role of XRE elements in mediating the induction of CBR1 by ligands of the aryl hydrocarbon receptor. Mol Pharmacol. 2007 Sep;72(3):734-43.
14 Flavonoids exhibit diverse effects on CYP11B1 expression and cortisol synthesis. Toxicol Appl Pharmacol. 2012 Feb 1;258(3):343-50.
15 Use of mRNA expression to detect the induction of drug metabolising enzymes in rat and human hepatocytes. Toxicol Appl Pharmacol. 2009 Feb 15;235(1):86-96.
16 Inter-laboratory evaluation of the response of primary human hepatocyte cultures to model CYP inducers - a European Centre for Validation of Alternative Methods (ECVAM) - funded pre-validation study. Toxicol In Vitro. 2010 Feb;24(1):335-45.
17 beta-Naphtoflavone and ethanol induce cytochrome P450 and protect towards MPP+ toxicity in human neuroblastoma SH-SY5Y cells. Int J Mol Sci. 2018 Oct 28;19(11).
18 Characterization of xenobiotic metabolizing enzymes of a reconstructed human epidermal model from adult hair follicles. Toxicol Appl Pharmacol. 2017 Aug 15;329:190-201.
19 Phloretamide, an apple phenolic compound, activates the Nrf2/ARE pathway in human hepatocytes. Food Chem Toxicol. 2013 Jan;51:202-9.
20 Thioredoxin reductase in human hepatoma cells is transcriptionally regulated by sulforaphane and other electrophiles via an antioxidant response element. J Nutr. 2003 Sep;133(9):2721-7.
21 Involvement of the xenobiotic response element (XRE) in Ah receptor-mediated induction of human UDP-glucuronosyltransferase 1A1. J Biol Chem. 2003 Apr 25;278(17):15001-6.
22 Stereoselective metabolism of carvedilol by the beta-naphthoflavone-inducible enzyme in human intestinal epithelial Caco-2 cells. Biol Pharm Bull. 2007 Oct;30(10):1930-3.

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