CHEBI:46195 - paracetamol

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ChEBI Name paracetamol
ChEBI ID CHEBI:46195
Definition A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46191, CHEBI:2386
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Formula C8H9NO2
Net Charge 0
Average Mass 151.16260
Monoisotopic Mass 151.063
InChI InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
InChIKey RZVAJINKPMORJF-UHFFFAOYSA-N
SMILES CC(=O)Nc1ccc(O)cc1
Metabolite of Species Details
Homo sapiens (NCBI:9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
cyclooxygenase 3 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.
Application(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
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ChEBI Ontology
Outgoing paracetamol (CHEBI:46195) has functional parent 4-aminophenol (CHEBI:17602)
paracetamol (CHEBI:46195) has role antipyretic (CHEBI:35493)
paracetamol (CHEBI:46195) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
paracetamol (CHEBI:46195) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
paracetamol (CHEBI:46195) has role cyclooxygenase 3 inhibitor (CHEBI:73263)
paracetamol (CHEBI:46195) has role environmental contaminant (CHEBI:78298)
paracetamol (CHEBI:46195) has role hepatotoxic agent (CHEBI:50908)
paracetamol (CHEBI:46195) has role human blood serum metabolite (CHEBI:85234)
paracetamol (CHEBI:46195) has role non-narcotic analgesic (CHEBI:35481)
paracetamol (CHEBI:46195) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
paracetamol (CHEBI:46195) has role xenobiotic (CHEBI:35703)
paracetamol (CHEBI:46195) is a acetamides (CHEBI:22160)
paracetamol (CHEBI:46195) is a phenols (CHEBI:33853)
Incoming 2-methoxyacetaminophen glucuronide (CHEBI:133005) has functional parent paracetamol (CHEBI:46195)
S-(5-acetamido-2-hydroxyphenyl)-N-acetyl-L-cysteine (CHEBI:133435) has functional parent paracetamol (CHEBI:46195)
S-(5-acetamido-2-hydroxyphenyl)cysteine (CHEBI:133066) has functional parent paracetamol (CHEBI:46195)
acetaminophen O-β-D-glucosiduronic acid (CHEBI:32636) has functional parent paracetamol (CHEBI:46195)
acetaminophen glutathione conjugate (CHEBI:32639) has functional parent paracetamol (CHEBI:46195)
paracetamol sulfate (CHEBI:32635) has functional parent paracetamol (CHEBI:46195)
IUPAC Name
N-(4-hydroxyphenyl)acetamide
INNs Sources
paracetamol KEGG DRUG
paracetamol WHO MedNet
paracétamol WHO MedNet
paracetamolum ChemIDplus
Synonyms Sources
4'-hydroxyacetanilide ChemIDplus
4-(Acetylamino)phenol ChemIDplus
4-acetamidophenol NIST Chemistry WebBook
Acenol ChemIDplus
acetaminofén ChemIDplus
Acetaminofen ChemIDplus
Acetaminophen KEGG COMPOUND
acétaminophène ChEBI
APAP DrugBank
N-acetyl-p-aminophenol ChEBI
p-acetamidophenol NIST Chemistry WebBook
p-acetaminophenol NIST Chemistry WebBook
p-Acetylaminophenol ChemIDplus
p-hydroxyacetanilide NIST Chemistry WebBook
p-hydroxyphenolacetamide NIST Chemistry WebBook
Paracetamol KEGG COMPOUND
Brand Names Sources
Panadol ChEBI
Tylenol KEGG DRUG
Database Links Databases
52 DrugCentral
Acetaminophen Wikipedia
C06804 KEGG COMPOUND
CPD-7669 MetaCyc
D00217 KEGG DRUG
DB00316 DrugBank
HMDB0001859 HMDB
LSM-5533 LINCS
TYL PDBeChem
View more database links
Registry Numbers Types Sources
103-90-2 CAS Registry Number KEGG COMPOUND
103-90-2 CAS Registry Number ChemIDplus
103-90-2 CAS Registry Number NIST Chemistry WebBook
2208089 Beilstein Registry Number Beilstein
2208089 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11084378 PubMed citation Europe PMC
11304127 PubMed citation Europe PMC
16716555 PubMed citation Europe PMC
18953082 PubMed citation Europe PMC
21108564 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
25128677 PubMed citation Europe PMC
27320817 PubMed citation Europe PMC
7602118 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag