Detail Information of Xenobiotics

General Information of Xenobiotics (ID: XEO00568)
Xenobiotics Name
Resveratrol
Xenobiotics Type
Pharmaceutical Agent(s)
Classification
Drug in Phase 3 Clinical Trial
Structure
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3D MOL 2D MOL
PubChem CID
445154
DME(s) Modulated by This Xenobiotics
DME(s) Inhibited by This Xenobiotics
Arachidonate 15-lipoxygenase (ALOX15) DME Info Homo sapiens [1]
Ampc beta-lactamase (ampC) DME Info Burkholderia cenocepacia [2]
AmpC beta-lactamase (ampC) DME Info Burkholderia multivorans [2]
Asparagine synthetase (ASNS) DME Info Homo sapiens [3]
Azoreductase (azoR) DME Info Escherichia coli [4]
L,D-carboxypeptidase A (ldcA) DME Info Escherichia coli [4]
Beta-lactamase (blaB) DME Info Escherichia coli [4]
Chloramphenicolase (chlR) DME Info Escherichia coli [4]
Glycoside hydrolase (cscA) DME Info Escherichia coli [4]
NADPH-dependent curcumin reductase (curA) DME Info Escherichia coli [4]
Steroid 17-alpha-monooxygenase (CYP17A1) DME Info Homo sapiens [5]
Aromatase (CYP19A1) DME Info Homo sapiens [6], [7]
Cytochrome P450 1A1 (CYP1A1) DME Info Homo sapiens [8]
Cytochrome P450 1A2 (CYP1A2) DME Info Homo sapiens [9], [10]
Cytochrome P450 1B1 (CYP1B1) DME Info Homo sapiens [8]
Steroid 21-hydroxylase (CYP21A2) DME Info Homo sapiens [11]
Mephenytoin 4-hydroxylase (CYP2C19) DME Info Homo sapiens [12]
Cytochrome P450 2C9 (CYP2C9) DME Info Homo sapiens [13], [10]
Cytochrome P450 2D6 (CYP2D6) DME Info Homo sapiens [5]
Cytochrome P450 3A4 (CYP3A4) DME Info Homo sapiens [12], [13]
Unclear metabolic mechanism (DME-unclear) DME Info Escherichia coli [4]
Glutamate decarboxylase (gadB) DME Info Escherichia coli [4]
HMG-CoA reductase (HMGCR) DME Info Homo sapiens [14]
D-Lactate dehydrogenase (ldhA) DME Info Escherichia coli [4]
D-Lactate dehydrogenase (ldhA) DME Info Pseudomonas aeruginosa [15]
Molybdopterin-dependent enzyme (molD) DME Info Escherichia coli [4]
Glutamate racemase (MurI) DME Info Escherichia coli [4]
Arylamine N-acetyltransferase (NAT) DME Info Pseudomonas aeruginosa [15]
N-ethylmaleimide reductase (nemA) DME Info Escherichia coli [4]
NADPH-dependent oxidoreductase (nfrA) DME Info Staphylococcus aureus [16]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME Info Escherichia coli [4]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME Info Escherichia coli [4]
Quinone reductase 1 (NQO1) DME Info Homo sapiens [11]
NADH dehydrogenase (nuoE) DME Info Streptomyces griseus [4]
Phosphodiesterase 5A (PDE5A) DME Info Homo sapiens [17]
Beta-lactamase (blaB) DME Info Burkholderia multivorans [2]
Beta-lactamase (blaB) DME Info Burkholderia cenocepacia [2]
Hydroxybenzoate 3-monooxygenase (pobA) DME Info Pseudomonas aeruginosa [15]
Prostaglandin G/H synthase 1 (COX-1) DME Info Homo sapiens [18], [19]
Prostaglandin G/H synthase 2 (COX-2) DME Info Homo sapiens [19]
Tyramine oxidase (tynA) DME Info Escherichia coli [4]
Beta-glucuronidase (uidA) DME Info Escherichia coli [4]
DME(s) Induced by This Xenobiotics
Aldehyde dehydrogenase 2 (ALDH2) DME Info Homo sapiens [11]
Catalase (CAT) DME Info Homo sapiens [11]
Cholesterol desmolase (CYP11A1) DME Info Homo sapiens [11]
Short-chain dehydrogenase/reductase retSDR1 (DHRS3) DME Info Homo sapiens [1]
Bifunctional epoxide hydrolase 2 (EPHX2) DME Info Homo sapiens [20]
Friedreich ataxia protein (FXN) DME Info Homo sapiens [21], [22]
Cellular glutathione peroxidase (GPX1) DME Info Homo sapiens [23]
Glutathione reductase (GSR) DME Info Homo sapiens [24]
Methionine adenosyltransferase II beta (MAT2B) DME Info Homo sapiens [25]
Methylsterol monooxygenase 1 (MSMO1) DME Info Homo sapiens [22]
Peptide methionine sulfoxide reductase (MSRA) DME Info Homo sapiens [26]
NADH-ubiquinone oxidoreductase 30 kDa (NDUFS3) DME Info Homo sapiens [27]
Nitric oxide synthase brain (NOS1) DME Info Homo sapiens [28]
Nitric oxide synthase endothelial (NOS3) DME Info Homo sapiens [29]
Serum paraoxonase/arylesterase 1 (PON1) DME Info Homo sapiens [30]
Superoxide dismutase 1 (SOD1) DME Info Homo sapiens [11], [31]
Sulfotransferase 1E1 (SULT1E1) DME Info Homo sapiens [11]
Tryptophan oxygenase (TRPO) DME Info Homo sapiens [30]
Transglutaminase K (TGM1) DME Info Homo sapiens [32]
Thioredoxin reductase TR1 (TXNRD1) DME Info Homo sapiens [33]
Thymidylate synthase (TYMS) DME Info Homo sapiens [34]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME Info Homo sapiens [11]
Xenobiotics-DME Activity Data
Xenobiotics-DME Activity Data Aromatase (CYP19A1) DME Info IC50 = 25 microM [6], [7]
Cytochrome P450 1A1 (CYP1A1) DME Info IC50 = 34 microM [8]
Cytochrome P450 1A2 (CYP1A2) DME Info IC50 = 3 microM [9], [10]
Cytochrome P450 1B1 (CYP1B1) DME Info IC50 = 55 microM [8]
Mephenytoin 4-hydroxylase (CYP2C19) DME Info IC50 = 3 microM [12]
Cytochrome P450 2C9 (CYP2C9) DME Info IC50 = 7 microM [13], [10]
Cytochrome P450 3A4 (CYP3A4) DME Info IC50 = 0.6 microM [12], [13]
Prostaglandin G/H synthase 1 (COX-1) DME Info IC50 = 0.625 microM [18], [19]
Prostaglandin G/H synthase 2 (COX-2) DME Info IC50 = 0.75 microM [19]
References
1 A transcriptomics-based in vitro assay for predicting chemical genotoxicity in vivo. Carcinogenesis. 2012 Jul;33(7):1421-9.
2 Use of quorum sensing inhibitors to interfere with biofilm formation and development in Burkholderia multivorans and Burkholderia cenocepacia. Res Microbiol. 2009 Mar;160(2):144-51.
3 The inhibitory effect of raloxifene on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells is mediated through a ROS/p38 MAPK/CREB pathway to the up-regulation of heme oxygenase-1 independent of estrogen receptor. Biochimie. 2011 Feb;93(2):168-74.
4 Diverse plant extracts and trans-resveratrol inhibit biofilm formation and swarming of Escherichia coli O157:H7. Biofouling. 2013;29(10):1189-203.
5 Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
6 Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol. Bioorg Med Chem. 2012 Apr 1;20(7):2427-34.
7 Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets. Bioorg Med Chem. 2012 Jan 1;20(1):510-20.
8 Aryl morpholino triazenes inhibit cytochrome P450 1A1 and 1B1. Bioorg Med Chem Lett. 2016 Jul 15;26(14):3243-3247.
9 Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2. J Pharmacol Exp Ther. 2001 Dec;299(3):874-82.
10 Trans-resveratrol, but not other natural stilbenes occurring in food, carries the risk of drug-food interaction via inhibition of cytochrome P450 enzymes or interaction with xenosensor receptors. Toxicol Lett. 2019 Jan;300:81-91.
11 Genomic and proteomic analysis of the inhibition of synthesis and secretion of aldosterone hormone induced by quinocetone in NCI-H295R cells. Toxicology. 2016 Mar 28;350-352:1-14.
12 Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate. Rapid Commun Mass Spectrom. 2003;17(4):307-13.
13 Functional expression and comparative characterization of nine murine cytochromes P450 by fluorescent inhibition screening. Drug Metab Dispos. 2008 Jul;36(7):1322-31.
14 Suppression of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells by chemopreventive agents with a resorcin-type structure. Carcinogenesis. 2000 May;21(5):959-63.
15 Inhibition of Pseudomonas aeruginosa and Escherichia coli O157:H7 biofilm formation by plant metabolite -viniferin. J Agric Food Chem. 2013 Jul 24;61(29):7120-6.
16 RNA-Seq-based transcriptome analysis of methicillin-resistant Staphylococcus aureus biofilm inhibition by ursolic acid and resveratrol. Sci Rep. 2014 Jun 27;4:5467.
17 Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure-activity relationship. Jpn J Cancer Res. 2000 Jul;91(7):686-91.
18 Synthetic and naturally occurring COX-2 inhibitors suppress proliferation in a human oesophageal adenocarcinoma cell line (OE33) by inducing apoptosis and cell cycle arrest. Carcinogenesis. 2004 Oct;25(10):1945-52.
19 Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites. J Med Chem. 2010 Jul 8;53(13):5033-43.
20 The THP-1 cell toolbox: a new concept integrating the key events of skin sensitization. Arch Toxicol. 2019 Apr;93(4):941-951.
21 Resveratrol modulates drug- and carcinogen-metabolizing enzymes in a healthy volunteer study. Cancer Prev Res (Phila). 2010 Sep;3(9):1168-75.
22 Resveratrol in human hepatoma HepG2 cells: metabolism and inducibility of detoxifying enzymes. Drug Metab Dispos. 2007 May;35(5):699-703.
23 Raloxifene induces cell death and inhibits proliferation through multiple signaling pathways in prostate cancer cells expressing different levels of estrogen receptor alpha and beta. J Cell Physiol. 2011 May;226(5):1334-9.
24 Quinone-mediated induction of cytochrome P450 1A1 in HepG2 cells through increased interaction of aryl hydrocarbon receptor with aryl hydrocarbon receptor nuclear translocator. J Toxicol Sci. 2016;41(6):775-781.
25 p53 Protects lung cancer cells against metabolic stress. Int J Oncol. 2010 Dec;37(6):1575-81.
26 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.
27 A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. Cutan Ocul Toxicol. 2010 Sep;29(3):171-92.
28 Transcriptional activity of quinone methides derived from the tumor promoter butylated hydroxytoluene in HepG2 cells. Cancer Lett. 1998 Sep 25;131(2):201-7.
29 Effects of benzimidazole derivatives on cytochrome P450 1A1 expression in a human hepatoma cell line. Xenobiotica. 1997 Jan;27(1):1-9.
30 Selenium supplementation restores the antioxidative capacity and prevents cell damage in bone marrow stromal cells in vitro. Stem Cells. 2006 May;24(5):1226-35.
31 Fused mesoionic heterocyclic compounds are a new class of aryl hydrocarbon receptor (AhR) agonist of exceptional potency. Toxicology. 2012 Dec 16;302(2-3):140-5.
32 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.
33 Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8.
34 Effects of calcitonin, risedronate, and raloxifene on erythrocyte antioxidant enzyme activity, lipid peroxidation, and nitric oxide in postmenopausal osteoporosis. Arch Med Res. 2007 Feb;38(2):196-205.

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