Detail Information of Xenobiotics

General Information of Xenobiotics (ID: XEO00557)
Xenobiotics Name
Genistein
Xenobiotics Type
Pharmaceutical Agent(s)
Classification
Drug in Phase 2 Clinical Trial
Structure
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3D MOL 2D MOL
PubChem CID
5280961
DME(s) Modulated by This Xenobiotics
DME(s) Inhibited by This Xenobiotics
Porphobilinogen synthase (ALAD) DME Info Homo sapiens [1]
Aldehyde dehydrogenase 1 (ALDH1) DME Info Homo sapiens [2]
Azoreductase (azoR) DME Info Escherichia coli [3]
L,D-carboxypeptidase A (ldcA) DME Info Escherichia coli [3]
Beta-lactamase (blaB) DME Info Escherichia coli [3]
Chloramphenicolase (chlR) DME Info Escherichia coli [3]
Catechol O-methyltransferase (COMT) DME Info Homo sapiens [4], [5]
Glycoside hydrolase (cscA) DME Info Escherichia coli [3]
NADPH-dependent curcumin reductase (curA) DME Info Escherichia coli [3]
Microsomal cytochrome MCB5 (CYB5A) DME Info Homo sapiens [6]
Aromatase (CYP19A1) DME Info Homo sapiens [7]
Cytochrome P450 1A1 (CYP1A1) DME Info Homo sapiens [8], [5]
Cytochrome P450 1A2 (CYP1A2) DME Info Homo sapiens [9]
Cytochrome P450 1B1 (CYP1B1) DME Info Homo sapiens [8]
Vitamin D(3) 24-hydroxylase (CYP24A1) DME Info Homo sapiens [10]
Mephenytoin 4-hydroxylase (CYP2C19) DME Info Homo sapiens [9]
Cytochrome P450 2C9 (CYP2C9) DME Info Homo sapiens [9]
Cytochrome P450 3A4 (CYP3A4) DME Info Homo sapiens [8]
Cytochrome P450 4B1 (CYP4B1) DME Info Homo sapiens [11]
Delta(24)-sterol reductase (DHCR24) DME Info Homo sapiens [12]
Unclear metabolic mechanism (DME-unclear) DME Info Escherichia coli [3]
Fatty acid desaturase 2 (FADS2) DME Info Homo sapiens [13]
Glutamate decarboxylase (gadB) DME Info Escherichia coli [3]
L-glutamine amidohydrolase (GLS) DME Info Homo sapiens [2]
Glutamine synthetase (GLUL) DME Info Homo sapiens [14]
Glutathione reductase (GSR) DME Info Homo sapiens [14]
Hypoxanthine phosphoribosyltransferase (HPRT1) DME Info Homo sapiens [15]
Estradiol 17-beta-dehydrogenase 1 (HSD17B1) DME Info Homo sapiens [16]
D-Lactate dehydrogenase (ldhA) DME Info Escherichia coli [3]
Molybdopterin-dependent enzyme (molD) DME Info Escherichia coli [3]
Glutamate racemase (MurI) DME Info Escherichia coli [3]
Mevalonate pyrophosphate decarboxylase (MPD) DME Info Homo sapiens [14]
N-ethylmaleimide reductase (nemA) DME Info Escherichia coli [3]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME Info Escherichia coli [3]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME Info Escherichia coli [3]
Nitric oxide synthase inducible (NOS2) DME Info Homo sapiens [17]
Quinone reductase 1 (NQO1) DME Info Homo sapiens [5]
Deoxy-5'-nucleotidase 1 (NT5C) DME Info Homo sapiens [15]
Ecto-5'-nucleotidase (NT5E) DME Info Homo sapiens [2]
NADH dehydrogenase (nuoE) DME Info Streptomyces griseus [3]
Prostaglandin G/H synthase 1 (COX-1) DME Info Homo sapiens [18]
Prostaglandin G/H synthase 2 (COX-2) DME Info Homo sapiens [19], [20]
Putrescine acetyltransferase (SSAT1) DME Info Homo sapiens [21]
Steroid 5-alpha-reductase 2 (SRD5A2) DME Info Homo sapiens [17]
Sulfotransferase 1E1 (SULT1E1) DME Info Homo sapiens [22], [23]
Tyramine oxidase (tynA) DME Info Escherichia coli [3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME Info Homo sapiens [22], [24]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME Info Homo sapiens [25]
Beta-glucuronidase (uidA) DME Info Escherichia coli [3]
DME(s) Induced by This Xenobiotics
Adenine phosphoribosyltransferase (APRT) DME Info Homo sapiens [6]
Asparagine synthetase (ASNS) DME Info Homo sapiens [6]
Butyrylcholine esterase (BCHE) DME Info Homo sapiens [12]
Carbonic anhydrase II (CA2) DME Info Homo sapiens [2]
Catalase (CAT) DME Info Homo sapiens [26]
NADPH-dependent carbonyl reductase 1 (CBR1) DME Info Homo sapiens [14]
Calcidiol 1-monooxygenase (CYP27B1) DME Info Homo sapiens [27]
Cholesterol 24-hydroxylase (CYP46A1) DME Info Homo sapiens [28]
Cytochrome P450 4F2 (CYP4F2) DME Info Homo sapiens [29]
Dicarbonyl/L-xylulose reductase (DCXR) DME Info Homo sapiens [28]
DOPA decarboxylase (DDC) DME Info Homo sapiens [12]
Short-chain dehydrogenase/reductase retSDR1 (DHRS3) DME Info Homo sapiens [2]
Thymidylate kinase (DTYMK) DME Info Homo sapiens [25]
Bifunctional epoxide hydrolase 2 (EPHX2) DME Info Homo sapiens [6]
Gamma-Glu-X carboxypeptidase (GGH) DME Info Homo sapiens [25]
Cellular glutathione peroxidase (GPX1) DME Info Homo sapiens [30]
Corticosteroid 11-beta-dehydrogenase 2 (HSD11B2) DME Info Homo sapiens [31]
Ketoacyl-CoA reductase (HSD17B12) DME Info Homo sapiens [2]
Monoamine oxidase type A (MAO-A) DME Info Homo sapiens [32]
Metallothionein-2A (MT2A) DME Info Homo sapiens [33]
Nitric oxide synthase endothelial (NOS3) DME Info Homo sapiens [34]
Superoxide dismutase 1 (SOD1) DME Info Homo sapiens [30]
Steroid 5-alpha-reductase 3 (SRD5A3) DME Info Homo sapiens [6]
Sulfotransferase 2A1 (SULT2A1) DME Info Homo sapiens [35]
Thioredoxin reductase TR1 (TXNRD1) DME Info Homo sapiens [11]
Thymidylate synthase (TYMS) DME Info Homo sapiens [25]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME Info Homo sapiens [36]
UDP-glucuronosyltransferase 2B17 (UGT2B17) DME Info Homo sapiens [37]
Xenobiotics-DME Activity Data
Xenobiotics-DME Activity Data Aromatase (CYP19A1) DME Info Ki = 100 microM [7]
Estradiol 17-beta-dehydrogenase 1 (HSD17B1) DME Info IC50 = 2.21 microM [16]
Prostaglandin G/H synthase 1 (COX-1) DME Info IC50 = 80 microM [18]
References
1 Moving toward integrating gene expression profiling into high-throughput testing: a gene expression biomarker accurately predicts estrogen receptor alpha modulation in a microarray compendium. Toxicol Sci. 2016 May;151(1):88-103.
2 Dose- and time-dependent transcriptional response of Ishikawa cells exposed to genistein. Toxicol Sci. 2016 May;151(1):71-87.
3 Apple flavonoid phloretin inhibits Escherichia coli O157:H7 biofilm formation and ameliorates colon inflammation in rats. Infect Immun. 2011 Dec;79(12):4819-27.
4 Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells. Carcinogenesis. 2008 Feb;29(2):363-70.
5 Phytoestrogens modulate the expression of 17alpha-estradiol metabolizing enzymes in cultured MCF-7 cells. Adv Exp Med Biol. 2008;617:625-32.
6 Quantitative proteomics and transcriptomics addressing the estrogen receptor subtype-mediated effects in T47D breast cancer cells exposed to the phytoestrogen genistein. Mol Cell Proteomics. 2011 Jan;10(1):M110.002170.
7 Screening of herbal constituents for aromatase inhibitory activity. Bioorg Med Chem. 2008 Sep 15;16(18):8466-70.
8 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.
9 Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.
10 Genistein potentiates the growth inhibitory effects of 1,25-dihydroxyvitamin D3 in DU145 human prostate cancer cells: role of the direct inhibition of CYP24 enzyme activity. Mol Cell Endocrinol. 2005 Sep 28;241(1-2):49-61.
11 Caffeine overcomes genistein-induced G2/M cell cycle arrest in breast cancer cells. Nutr Cancer. 2008;60(3):382-8.
12 Using DNA microarray analyses to elucidate the effects of genistein in androgen-responsive prostate cancer cells: identification of novel targets. Mol Carcinog. 2004 Oct;41(2):108-119.
13 Anti-inflammatory effects of dietary phenolic compounds in an in vitro model of inflamed human intestinal epithelium. Chem Biol Interact. 2010 Dec 5;188(3):659-67.
14 Changes in gene expressions elicited by physiological concentrations of genistein on human endometrial cancer cells. Mol Carcinog. 2006 Oct;45(10):752-63.
15 A high concentration of genistein down-regulates activin A, Smad3 and other TGF-beta pathway genes in human uterine leiomyoma cells. Exp Mol Med. 2012 Apr 30;44(4):281-92.
16 Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries. J Med Chem. 2008 Jul 24;51(14):4188-99.
17 Examining the genomic influence of skin antioxidants in vitro. Mediators Inflamm. 2010;2010.
18 Expanding the ChemGPS chemical space with natural products. J Nat Prod. 2005 Jul;68(7):985-91.
19 Anti-inflammatory and anticarcinogenic effect of genistein alone or in combination with capsaicin in TPA-treated rat mammary glands or mammary cancer cell line. Ann N Y Acad Sci. 2009 Aug;1171:415-20.
20 Genistein potentiates the effect of arsenic trioxide against human hepatocellular carcinoma: role of Akt and nuclear factor-B. Cancer Lett. 2011 Feb 1;301(1):75-84.
21 Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. Toxicol Appl Pharmacol. 2009 Apr 1;236(1):85-96.
22 Effects of endocrine disruptors on genes associated with 17beta-estradiol metabolism and excretion. Steroids. 2008 Nov;73(12):1242-51.
23 Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase. Anal Biochem. 2006 Oct 1;357(1):85-92.
24 Isoflavones modulate the glucuronidation of estradiol in human liver microsomes. Carcinogenesis. 2005 Dec;26(12):2172-8.
25 Convergent transcriptional profiles induced by endogenous estrogen and distinct xenoestrogens in breast cancer cells. Carcinogenesis. 2006 Aug;27(8):1567-78.
26 The antioxidant effects of genistein are associated with AMP-activated protein kinase activation and PTEN induction in prostate cancer cells. J Med Food. 2010 Aug;13(4):815-20.
27 25-Hydroxyvitamin D3-1alpha-hydroxylase is expressed in human vascular smooth muscle cells and is upregulated by parathyroid hormone and estrogenic compounds. Circulation. 2005 Apr 5;111(13):1666-71.
28 The molecular basis of genistein-induced mitotic arrest and exit of self-renewal in embryonal carcinoma and primary cancer cell lines. BMC Med Genomics. 2008 Oct 10;1:49.
29 Genistein, resveratrol, and 5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside induce cytochrome P450 4F2 expression through an AMP-activated protein kinase-dependent pathway. J Pharmacol Exp Ther. 2011 Apr;337(1):125-36.
30 A high-throughput reporter gene assay to prove the ability of natural compounds to modulate glutathione peroxidase, superoxide dismutase and catalase gene promoters in V79 cells. Free Radic Res. 2008 Aug;42(8):746-53.
31 Genistein and bisphenol A exposure cause estrogen receptor 1 to bind thousands of sites in a cell type-specific manner. Genome Res. 2012 Nov;22(11):2153-62.
32 Oestrogenic potencies of Zeranol, oestradiol, diethylstilboestrol, Bisphenol-A and genistein: implications for exposure assessment of potential endocrine disrupters. Hum Reprod. 2001 May;16(5):1037-45.
33 Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids. Cancer Lett. 1999 Nov 15;146(2):161-7.
34 The isoflavone Equol mediates rapid vascular relaxation: Ca2+-independent activation of endothelial nitric-oxide synthase/Hsp90 involving ERK1/2 and Akt phosphorylation in human endothelial cells. J Biol Chem. 2006 Sep 15;281(37):27335-45.
35 Liver X receptor alpha mediated genistein induction of human dehydroepiandrosterone sulfotransferase (hSULT2A1) in Hep G2 cells. Toxicol Appl Pharmacol. 2013 Apr 15;268(2):106-12.
36 Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells. Toxicol In Vitro. 2013 Aug;27(5):1467-75.
37 Molecular signatures of soy-derived phytochemicals in androgen-responsive prostate cancer cells: a comparison study using DNA microarray. Mol Carcinog. 2006 Dec;45(12):943-56.

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