CHEBI:28939 - N-acetyl-L-cysteine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways
ChEBI Name N-acetyl-L-cysteine
ChEBI ID CHEBI:28939
ChEBI ASCII Name N-acetyl-L-cysteine
Definition An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45481, CHEBI:2418, CHEBI:21548
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Formula C5H9NO3S
Net Charge 0
Average Mass 163.19590
InChI InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
InChIKey PWKSKIMOESPYIA-BYPYZUCNSA-N
SMILES CC(=O)N[C@@H](CS)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:9606) See: DOI
Homo sapiens (NCBI:9606) See: MetaboLights Study
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
Application(s): antidote to paracetamol poisoning
A role borne by a molecule that acts to counteract or neutralize the deleterious effects of paracetamol (acetaminophen).
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
mucolytic
A compound that alters the structure of mucus so as to decrease its viscosity and thereby facilitate its removal by ciliary action and expectoration. Compare with antitussives, which suppress the cough reflex, and expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing.
vulnerary
A drug used in treating and healing of wounds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-acetyl-L-cysteine (CHEBI:28939) has role antidote to paracetamol poisoning (CHEBI:74529)
N-acetyl-L-cysteine (CHEBI:28939) has role antiinfective agent (CHEBI:35441)
N-acetyl-L-cysteine (CHEBI:28939) has role antioxidant (CHEBI:22586)
N-acetyl-L-cysteine (CHEBI:28939) has role antiviral drug (CHEBI:36044)
N-acetyl-L-cysteine (CHEBI:28939) has role human metabolite (CHEBI:77746)
N-acetyl-L-cysteine (CHEBI:28939) has role mucolytic (CHEBI:77034)
N-acetyl-L-cysteine (CHEBI:28939) has role radical scavenger (CHEBI:48578)
N-acetyl-L-cysteine (CHEBI:28939) has role vulnerary (CHEBI:73336)
N-acetyl-L-cysteine (CHEBI:28939) is a N-acetyl-L-amino acid (CHEBI:21545)
N-acetyl-L-cysteine (CHEBI:28939) is a L-cysteine derivative (CHEBI:83824)
N-acetyl-L-cysteine (CHEBI:28939) is a acetylcysteine (CHEBI:22198)
N-acetyl-L-cysteine (CHEBI:28939) is conjugate acid of N-acetyl-L-cysteinate (CHEBI:78236)
Incoming S-substituted N-acetyl-L-cysteine (CHEBI:47911) has functional parent N-acetyl-L-cysteine (CHEBI:28939)
N-acetyl-L-cysteinate (CHEBI:78236) is conjugate base of N-acetyl-L-cysteine (CHEBI:28939)
IUPAC Name
N-acetyl-L-cysteine
INNs Sources
acetilcisteina ChemIDplus
acetylcysteinum ChemIDplus
Synonyms Sources
(2R)-2-acetylamino-3-sulfanylpropanoic acid IUPAC
(R)-2-acetylamino-3-mercaptopropanoic acid ChEBI
(R)-mercapturic acid ChemIDplus
Acetylcysteine KEGG COMPOUND
L-acetylcysteine ChemIDplus
L-α-acetamido-β-mercaptopropionic acid NIST Chemistry WebBook
mercapturic acid ChemIDplus
N-acetyl-L-(+)-cysteine NIST Chemistry WebBook
N-ACETYL-L-CYSTEINE PDBeChem
N-acetylcysteine ChemIDplus
NAC ChEBI
Database Links Databases
Acetylcysteine Wikipedia
C06809 KEGG COMPOUND
CPD-9175 MetaCyc
D00221 KEGG DRUG
DB06151 DrugBank
HMDB01890 HMDB
LSM-4672 LINCS
SC2 PDBeChem
View more database links
Registry Numbers Types Sources
142554 Gmelin Registry Number Gmelin
1724426 Beilstein Registry Number Beilstein
1724426 Reaxys Registry Number Reaxys
616-91-1 CAS Registry Number KEGG COMPOUND
616-91-1 CAS Registry Number NIST Chemistry WebBook
616-91-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10651166 PubMed citation CiteXplore
17174578 PubMed citation CiteXplore
2026726 PubMed citation CiteXplore
24119926 PubMed citation CiteXplore
25553484 PubMed citation CiteXplore
Last Modified
25 February 2016