Detail Information of Xenobiotics

General Information of Xenobiotics (ID: XEO00217)
Xenobiotics Name
Acetaminophen
Xenobiotics Type
Pharmaceutical Agent(s)
Classification
Approved/Marketed Drug
Structure
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3D MOL 2D MOL
PubChem CID
1983
DME(s) Modulated by This Xenobiotics
DME(s) Inhibited by This Xenobiotics
Acyl-CoA thioesterase 2 (ACOT2) DME Info Homo sapiens [1], [2]
Acid phosphatase-like protein 1 (ACP6) DME Info Homo sapiens [3]
Acetyl-CoA synthetase (ACSS2) DME Info Homo sapiens [2]
Adenosine aminohydrolase (ADA) DME Info Homo sapiens [2]
Alcohol dehydrogenase class-I gamma (ADH1C) DME Info Homo sapiens [4]
Alcohol dehydrogenase class-II (ADH4) DME Info Homo sapiens [2]
Alcohol dehydrogenase class-III (ADH5) DME Info Homo sapiens [2]
Alcohol dehydrogenase class-V (ADH6) DME Info Homo sapiens [2]
Small intestine reductase (AKR1B10) DME Info Homo sapiens [4], [2]
Aldo-keto reductase 1C2 (AKR1C2) DME Info Homo sapiens [2]
Aldo-keto reductase 1C3 (AKR1C3) DME Info Homo sapiens [4]
Aldo-keto reductase 1C4 (AKR1C4) DME Info Homo sapiens [2]
Aldo-keto reductase 1D1 (AKR1D1) DME Info Homo sapiens [2]
Porphobilinogen synthase (ALAD) DME Info Homo sapiens [2]
Aldehyde dehydrogenase 1 (ALDH1) DME Info Homo sapiens [4], [2]
Aldehyde dehydrogenase 5 (ALDHX) DME Info Homo sapiens [3], [2]
Aldehyde dehydrogenase 2 (ALDH2) DME Info Homo sapiens [3]
Succinate-semialdehyde dehydrogenase (ALDH5A1) DME Info Homo sapiens [2]
Aminomuconic semialdehyde dehydrogenase (ALDH12) DME Info Homo sapiens [4]
Arachidonate 15-lipoxygenase (ALOX15) DME Info Homo sapiens [5]
Alkaline phosphatase (ALPL) DME Info Homo sapiens [4], [2]
Alanyl aminopeptidase (ANPEP) DME Info Homo sapiens [2]
Amiloride-sensitive amine oxidase (AOC1) DME Info Homo sapiens [2]
Aldehyde oxidase (AOX1) DME Info Homo sapiens [2]
Aquaporin adipose (AQP7) DME Info Homo sapiens [5], [2]
Arylsulfatase B (ARSB) DME Info Homo sapiens [3]
Bile acid-CoA thioesterase (BAAT) DME Info Homo sapiens [2]
Cytosolic branched aminotransferase (BCAT1) DME Info Homo sapiens [4]
Butyrylcholine esterase (BCHE) DME Info Homo sapiens [2]
Beta,beta-carotene 15,15'-dioxygenase (BCO1) DME Info Homo sapiens [1]
Catalase (CAT) DME Info Homo sapiens [2]
NADPH-dependent carbonyl reductase 1 (CBR1) DME Info Homo sapiens [1], [2]
Serine sulfhydrase (CBS) DME Info Homo sapiens [1]
Carboxylesterase 1 (CES1) DME Info Homo sapiens [5]
Carboxylesterase 2 (CES2) DME Info Homo sapiens [4], [2]
Choline dehydrogenase (CHDH) DME Info Homo sapiens [5], [3]
Microsomal cytochrome MCB5 (CYB5A) DME Info Homo sapiens [3], [2]
Cytochrome P450 1A1 (CYP1A1) DME Info Homo sapiens [2]
Cytochrome P450 1B1 (CYP1B1) DME Info Homo sapiens [5]
Steroid 21-hydroxylase (CYP21A2) DME Info Homo sapiens [4], [2]
Retinoic acid 4-hydroxylase 26A1 (CYP26A1) DME Info Homo sapiens [4]
Vitamin D(3) 25-hydroxylase (CYP27A1) DME Info Homo sapiens [5]
Calcidiol 1-monooxygenase (CYP27B1) DME Info Homo sapiens [3]
Cytochrome P450 2A6 (CYP2A6) DME Info Homo sapiens [2]
Cytochrome P450 2B6 (CYP2B6) DME Info Homo sapiens [2]
Cytochrome P450 2C18 (CYP2C18) DME Info Homo sapiens [4], [2]
Mephenytoin 4-hydroxylase (CYP2C19) DME Info Homo sapiens [2]
Cytochrome P450 2C8 (CYP2C8) DME Info Homo sapiens [2]
Cytochrome P450 2C9 (CYP2C9) DME Info Homo sapiens [2]
Cytochrome P450 2E1 (CYP2E1) DME Info Homo sapiens [2]
Cytochrome P450 2J2 (CYP2J2) DME Info Homo sapiens [6]
Cytochrome P450 3A4 (CYP3A4) DME Info Homo sapiens [2]
Cytochrome P450 3A5 (CYP3A5) DME Info Homo sapiens [2]
Cytochrome P450 3A7 (CYP3A7) DME Info Homo sapiens [7], [2]
Cytochrome P450 4B1 (CYP4B1) DME Info Homo sapiens [2]
Cytochrome P450 4F2 (CYP4F2) DME Info Homo sapiens [5]
DOPA decarboxylase (DDC) DME Info Homo sapiens [2]
Delta(24)-sterol reductase (DHCR24) DME Info Homo sapiens [2]
Short-chain dehydrogenase/reductase retSDR1 (DHRS3) DME Info Homo sapiens [4], [2]
Dihydrothymine dehydrogenase (DPYD) DME Info Homo sapiens [2]
Bifunctional epoxide hydrolase 2 (EPHX2) DME Info Homo sapiens [2]
Fatty acid desaturase 1 (FADS1) DME Info Homo sapiens [2]
Fatty acid desaturase 2 (FADS2) DME Info Homo sapiens [4]
Dimethylaniline oxidase 3 (FMO3) DME Info Homo sapiens [2]
Folylpolyglutamate synthase (FPGS) DME Info Homo sapiens [3]
Friedreich ataxia protein (FXN) DME Info Homo sapiens [3], [8]
Glutamyl-tRNA(Gln) amidotransferase B (GATB) DME Info Homo sapiens [2]
Glutamine synthetase (GLUL) DME Info Homo sapiens [1], [2]
Cellular glutathione peroxidase (GPX1) DME Info Homo sapiens [8]
Glutathione S-transferase mu-1 (GSTM1) DME Info Homo sapiens [2]
Glutathione S-transferase omega-1 (GSTO1) DME Info Homo sapiens [2]
Adenosine 5'-monophosphoramidase (HINT1) DME Info Homo sapiens [4]
HMG-CoA reductase (HMGCR) DME Info Homo sapiens [2]
Histamine N-methyltransferase (HNMT) DME Info Homo sapiens [4], [2]
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) DME Info Homo sapiens [2]
Corticosteroid 11-beta-dehydrogenase 2 (HSD11B2) DME Info Homo sapiens [2]
Estradiol 17-beta-dehydrogenase 2 (HSD17B2) DME Info Homo sapiens [4], [2]
Testicular 17-beta-hydroxysteroid dehydrogenase (HSD17B3) DME Info Homo sapiens [2]
Peroxisomal multifunctional enzyme 2 (HSD17B4) DME Info Homo sapiens [3], [2]
Keto-steroid reductase (HSD17B7) DME Info Homo sapiens [2]
Monoamine oxidase type A (MAO-A) DME Info Homo sapiens [2]
Monoamine oxidase type B (MAO-B) DME Info Homo sapiens [3], [2]
S-adenosylmethionine synthase 1 (MAT1A) DME Info Homo sapiens [2]
Microsomal glutathione S-transferase 2 (MGST2) DME Info Homo sapiens [4], [2]
Neprilysin (MME) DME Info Homo sapiens [2]
Methylsterol monooxygenase 1 (MSMO1) DME Info Homo sapiens [1], [2]
Methionine-R-sulfoxide reductase B1 (MSRB1) DME Info Homo sapiens [4], [2]
Methionine-R-sulfoxide reductase B2 (MSRB2) DME Info Homo sapiens [2]
Methylenetetrahydrofolate reductase (MTHFR) DME Info Homo sapiens [4]
Vitamin B12 methionine synthase (MTR) DME Info Homo sapiens [4]
Methionine synthase reductase (MTRR) DME Info Homo sapiens [3]
N-acetyltransferase 2 (NAT2) DME Info Homo sapiens [4], [2]
Cysteinyl-conjugate N-acetyltransferase (NAT8) DME Info Homo sapiens [4]
NADH-ubiquinone oxidoreductase 49 kDa (NDUFS2) DME Info Homo sapiens [8]
NADH-ubiquinone oxidoreductase 30 kDa (NDUFS3) DME Info Homo sapiens [8], [2]
Quinone reductase 1 (NQO1) DME Info Homo sapiens [9]
Deoxy-5'-nucleotidase 1 (NT5C) DME Info Homo sapiens [1]
Ecto-5'-nucleotidase (NT5E) DME Info Homo sapiens [1], [4]
Propionyl-CoA carboxylase beta (PCCB) DME Info Homo sapiens [3], [2]
Phosphorylethanolamine transferase (PCYT2) DME Info Homo sapiens [2]
Phosphodiesterase 7B (PDE7B) DME Info Homo sapiens [2]
Phosphoribosylformylglycinamidine synthase (PFAS) DME Info Homo sapiens [4]
Phosphoglucomutase 1 (PGM1) DME Info Homo sapiens [4]
Cytosolic phospholipase A2 (PLA2G4A) DME Info Homo sapiens [2]
Choline phosphatase 1 (PLD1) DME Info Homo sapiens [4]
Pyridoxamine-phosphate oxidase (PNPO) DME Info Homo sapiens [2]
Serum paraoxonase/arylesterase 1 (PON1) DME Info Homo sapiens [2]
Serum paraoxonase/lactonase 3 (PON3) DME Info Homo sapiens [2]
Proline dehydrogenase 1 (PRODH) DME Info Homo sapiens [2]
Prostaglandin reductase 1 (PTGR1) DME Info Homo sapiens [4], [2]
Prostaglandin G/H synthase 1 (COX-1) DME Info Homo sapiens [10]
Prostaglandin G/H synthase 2 (COX-2) DME Info Homo sapiens [11]
Selenocysteine lyase (SCLY) DME Info Homo sapiens [4]
Superoxide dismutase 1 (SOD1) DME Info Homo sapiens [12]
Steroid 5-alpha-reductase 3 (SRD5A3) DME Info Homo sapiens [5]
Sulfotransferase 1A1 (SULT1A1) DME Info Homo sapiens [2]
Sulfotransferase 1A2 (SULT1A2) DME Info Homo sapiens [2]
Sulfotransferase 1B1 (SULT1B1) DME Info Homo sapiens [2]
Sulfotransferase 2A1 (SULT2A1) DME Info Homo sapiens [2]
Sulfotransferase 2B1 (SULT2B1) DME Info Homo sapiens [5]
Transglutaminase H (TGM2) DME Info Homo sapiens [4]
Transglutaminase Z (TGM7) DME Info Homo sapiens [5]
Thymidine phosphorylase (TYMP) DME Info Homo sapiens [4]
Thymidylate synthase (TYMS) DME Info Homo sapiens [4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME Info Homo sapiens [13]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME Info Homo sapiens [2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME Info Homo sapiens [2]
UDP-glucuronosyltransferase 2A3 (UGT2A3) DME Info Homo sapiens [2]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME Info Homo sapiens [2]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME Info Homo sapiens [2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME Info Homo sapiens [2]
Uridine phosphorylase 2 (UPP2) DME Info Homo sapiens [5]
Tryptophanyl-tRNA synthetase mitochondrial (WARS2) DME Info Homo sapiens [3], [8]
Xanthine dehydrogenase/oxidase (XDH) DME Info Homo sapiens [4], [2]
DME(s) Induced by This Xenobiotics
Alcohol dehydrogenase class-I alpha (ADH1A) DME Info Homo sapiens [14]
Gastric alcohol dehydrogenase (ADH7) DME Info Homo sapiens [5]
Hydroxyacid-oxoacid transhydrogenase (ADHFE1) DME Info Homo sapiens [5]
Aldo-keto reductase 1B1 (AKR1B1) DME Info Homo sapiens [1]
Aldo-keto reductase 1C1 (AKR1C1) DME Info Homo sapiens [4]
Succinic semialdehyde reductase (AKR7A2) DME Info Homo sapiens [3]
Arsenite methyltransferase (AS3MT) DME Info Homo sapiens [1]
Asparagine synthetase (ASNS) DME Info Homo sapiens [14]
NADPH-dependent carbonyl reductase 3 (CBR3) DME Info Homo sapiens [4]
Cathepsin A (CTSA) DME Info Homo sapiens [3]
Aromatase (CYP19A1) DME Info Homo sapiens [5]
Cytochrome P450 3A43 (CYP3A43) DME Info Homo sapiens [1]
Cytochrome P450 4F12 (CYP4F12) DME Info Homo sapiens [1]
Leukotriene B4 omega-hydroxylase (CYP4F3) DME Info Homo sapiens [1]
Dicarbonyl/L-xylulose reductase (DCXR) DME Info Homo sapiens [1]
Dihydrofolate reductase (DHFR) DME Info Homo sapiens [1]
Dipeptidyl peptidase IV (DPP4) DME Info Homo sapiens [1]
Thymidylate kinase (DTYMK) DME Info Homo sapiens [1]
Eosinophil peroxidase (EPX) DME Info Homo sapiens [5]
Oleamide hydrolase 1 (FAAH) DME Info Homo sapiens [1]
Sodium/potassium-transporting ATPase gamma (FXYD2) DME Info Homo sapiens [1]
Gamma-Glu-X carboxypeptidase (GGH) DME Info Homo sapiens [1]
L-glutamine amidohydrolase (GLS) DME Info Homo sapiens [5]
Glutathione reductase (GSR) DME Info Homo sapiens [8]
Glutathione S-transferase alpha-1 (GSTA1) DME Info Homo sapiens [5]
Glutathione S-transferase theta-1 (GSTT1) DME Info Homo sapiens [2]
Beta-glucuronidase (GUSB) DME Info Homo sapiens [15]
N-acetyl-beta-glucosaminidase beta (HEXB) DME Info Homo sapiens [1]
Heparanase (HPSE) DME Info Homo sapiens [4]
Mevalonate pyrophosphate decarboxylase (MPD) DME Info Homo sapiens [5]
Phosphodiesterase 5A (PDE5A) DME Info Homo sapiens [2]
Purine nucleoside phosphorylase (PNP) DME Info Homo sapiens [4]
NADPH-cytochrome P450 reductase (CPR) DME Info Homo sapiens [4]
Amidophosphoribosyltransferase (GPAT) DME Info Homo sapiens [5]
Xylosyl phosphatase (PXYLP1) DME Info Homo sapiens [4]
Putrescine acetyltransferase (SSAT1) DME Info Homo sapiens [4], [2]
Sulfotransferase 1C4 (SULT1C4) DME Info Homo sapiens [1]
Thioredoxin reductase TR1 (TXNRD1) DME Info Homo sapiens [1]
Uridine phosphorylase 1 (UPP1) DME Info Homo sapiens [2]
Xenobiotics-DME Activity Data
Xenobiotics-DME Activity Data Cytochrome P450 2J2 (CYP2J2) DME Info IC50 > 50 microM [6]
Prostaglandin G/H synthase 1 (COX-1) DME Info IC50 = 200 microM [10]
Prostaglandin G/H synthase 2 (COX-2) DME Info IC50 = 141 microM [11]
References
1 Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):270-80.
2 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
3 Increased mitochondrial ROS formation by acetaminophen in human hepatic cells is associated with gene expression changes suggesting disruption of the mitochondrial electron transport chain. Toxicol Lett. 2015 Apr 16;234(2):139-50.
4 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.
5 Blood transcript immune signatures distinguish a subset of people with elevated serum ALT from others given acetaminophen. Clin Pharmacol Ther. 2016 Apr;99(4):432-41.
6 Discovery and characterization of novel, potent, and selective cytochrome P450 2J2 inhibitors. Drug Metab Dispos. 2013 Jan;41(1):60-71.
7 Toxicogenomics-based prediction of acetaminophen-induced liver injury using human hepatic cell systems. Toxicol Lett. 2016 Jan 5;240(1):50-9.
8 Human 3D multicellular microtissues: an upgraded model for the in vitro mechanistic investigation of inflammation-associated drug toxicity. Toxicol Lett. 2019 Sep 15;312:34-44.
9 Natural polyphenol chlorogenic acid protects against acetaminophen-induced hepatotoxicity by activating ERK/Nrf2 antioxidative pathway. Toxicol Sci. 2018 Mar 1;162(1):99-112.
10 Impact of binding site comparisons on medicinal chemistry and rational molecular design. J Med Chem. 2016 May 12;59(9):4121-51.
11 New analgesics synthetically derived from the paracetamol metabolite N-(4-hydroxyphenyl)-(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-enamide. J Med Chem. 2008 Dec 25;51(24):7800-5.
12 Hepatic 3D cultures but not 2D cultures preserve specific transporter activity for acetaminophen-induced hepatotoxicity. Arch Toxicol. 2013 Aug;87(8):1581-93.
13 In vitro inhibitory effects of non-steroidal antiinflammatory drugs on UDP-glucuronosyltransferase 1A1-catalysed estradiol 3beta-glucuronidation in human liver microsomes. Biopharm Drug Dispos. 2005 Jan;26(1):35-9.
14 Comparison of base-line and chemical-induced transcriptomic responses in HepaRG and RPTEC/TERT1 cells using TempO-Seq. Arch Toxicol. 2018 Aug;92(8):2517-2531.
15 Selected biochemical parameters of urine in the evaluation of paracetamol nephrotoxicity. Przegl Lek. 2006;63(12):1299-303.

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