ACETAMINOPHEN

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Trade Names
Synonyms
Status
Molecule Category Free-form
UNII 362O9ITL9D
EPA CompTox DTXSID2020006

Structure

InChI Key RZVAJINKPMORJF-UHFFFAOYSA-N
Smiles CC(=O)Nc1ccc(O)cc1
InChI
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H9NO2
Molecular Weight 151.16
AlogP 1.35
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 49.33
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 11.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Anandamide amidohydrolase inhibitor INHIBITOR Wikipedia PubMed
Protein: Anandamide amidohydrolase
Description: Fatty-acid amide hydrolase 1
Organism : Homo sapiens
O00519 ENSG00000117480
Protein: Cyclooxygenase
Description: Prostaglandin G/H synthase 1
Organism : Homo sapiens
P23219 ENSG00000095303
Protein: Cyclooxygenase
Description: Prostaglandin G/H synthase 2
Organism : Homo sapiens
P35354 ENSG00000073756
Protein: Vanilloid receptor
Description: Transient receptor potential cation channel subfamily V member 1
Organism : Homo sapiens
Q8NER1 ENSG00000196689
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A1
- - 19100 - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2E Cytochrome P450 2E1
- - - - 50
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 50
Enzyme Hydrolase
- - - - 20-34
Enzyme Lyase
- - - 10000-10000 -
Enzyme
- - 19100 10000-10000 20-34
Epigenetic regulator Reader Bromodomain
- - - - 12
Other cytosolic protein
- 44000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 100
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Unclassified protein
- 2300 - - -
Assay Description Organism Bioactivity Reference
Inhibition of recombinant human AKR1C3 at 50 uM Homo sapiens 8.0 %
Antinociceptive activity in Swiss mouse assessed as reduction of acetic acid-induced abdominal constructions at 1 to 10 mg/kg, ip administered 30 mins before acetic acid challenge measured after 20 mins relative to control Mus musculus 88.0 %
Antinociceptive activity in Swiss mouse assessed as reduction of formalin-induced inflammatory pain at 1 to 10 mg/kg, ip administered 60 mins before formalin challenge measured during 15 to 30 mins relative to control Mus musculus 85.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -9.2 %
Antinociceptive activity against acetic acid-induced abdominal constrictions in Swiss mouse assessed as maximal inhibition at 10 mg/kg, ip pretreated 30 mins before acetic acid challenge Mus musculus 38.0 %
Inhibition of FAAH in rat brain membrane assessed as [14C]anandamide hydrolysis at 50 uM by scintillation counting Rattus norvegicus 22.0 %
Antinociceptive activity in mouse assessed as inhibition of acetic acid-induced abdominal constrictions at 100 umol/kg, po relative to untreated control Mus musculus 36.0 %
Antinociceptive activity in Swiss mouse by inhibition of acetic acid-induced abdominal constriction at 10 mg/kg, ip after 20 mins Mus musculus 38.0 %
Inhibition of FAAH-mediated [3H]AEA hydrolysis in rat brain homogenate at 300 uM by liquid scintillation spectroscopy Rattus norvegicus 4.0 %
Inhibition of human recombinant MGL at 1000 uM Homo sapiens 34.0 %
Inhibition of human recombinant MGL at 300 uM Homo sapiens 20.0 %
Antiparasitic activity against Trichomonas vaginalis T1 at 100 uM after 24 hrs by hemocytometric analysis Trichomonas vaginalis 17.0 %
Antiparasitic activity against Trichomonas vaginalis G3 at 100 uM after 24 hrs by hemocytometric analysis Trichomonas vaginalis G3 14.0 %
Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 0.50 % after 24 hrs relative to control Staphylococcus aureus 10.8 %
Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 0.10 % after 24 hrs relative to control Staphylococcus aureus 56.3 %
Inhibition of His-6 tagged BRD2-RD12 precoupled with biotinylated tetra-acetylated histone H4 expressed in Escherichia coli assessed as protein-protein interaction at 50 uM after 1 hr by TR-FRET assay None 6.0 %
Inhibition of His-6 tagged BRD3-RD12 precoupled with biotinylated tetra-acetylated histone H4 expressed in Escherichia coli assessed as protein-protein interaction at 50 uM after 1 hr by TR-FRET assay None 19.0 %
Inhibition of His-6 tagged BRD4-RD12 precoupled with biotinylated tetra-acetylated histone H4 expressed in Escherichia coli assessed as protein-protein interaction at 50 uM after 1 hr by TR-FRET assay None 12.0 %
Analgesic activity in Mus musculus Swiss albino (mouse) assessed as inhibition of acetic acid-induced writhing at 100 mg/kg, ip measured after 30 min relative to control Mus musculus 29.38 %
Inhibition of Capra hircus (goat) brain DPP-3 using Arg-Arg-4mbetaNA as substrate assessed as liberation of 4mbetaNA from substrate Capra hircus 96.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 99.98 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 96.68 %
Antiangiogenic activity in chicken chorioallantoic membrane assessed as inhibition of VEGF-induced blood vessel formation at 0.01 nmol/CAM treated 30 mins after VEGF addition measured after 3 days relative to control Gallus gallus 77.9 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 10 uM by LC/MS system Homo sapiens 10.0 %
Analgesic activity in po dosed Japanese chronic pain patient (5 patients) assessed as compound dose require to cause 50% maximum pain relief score administered as single dose measured over 15 mins to 6 hrs Homo sapiens 2.0 ug.mL-1
Antiangiogenic activity in HUVEC assessed as inhibition of tube formation on matrigel at 12.5 ug/ml after 24 hrs by Mayer's hematoxylin staining based light microscopy relative to control Homo sapiens 10.47 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -1.06 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.03 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.3 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.3 %
Inhibition of CYP3A4 (unknown origin) in baculosomes preincubated for 20 mins followed by addition of CYP enzyme-specific substrate and NADP+ and measured after 30 mins by fluorescence based analysis relative to control Homo sapiens 50.0 %
Inhibition of CYP2E1 (unknown origin) in baculosomes preincubated for 20 mins followed by addition of CYP enzyme-specific substrate and NADP+ and measured after 30 mins by fluorescence based analysis relative to control Homo sapiens 50.0 %

Related Entries

Cross References

Resources Reference
ChEBI 46195
ChEMBL CHEMBL112
DrugBank DB00316
DrugCentral 52
FDA SRS 362O9ITL9D
Human Metabolome Database HMDB0001859
Guide to Pharmacology 5239
KEGG C06804
PDB TYL
PharmGKB PA448015
PubChem 1983
SureChEMBL SCHEMBL3480
ZINC ZINC000013550868
CONTENTS