N-acetyl-L-cysteine (CHEBI:28939)

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CHEBI:28939 - N-acetyl-L-cysteine

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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

Supplier Information	ChemicalBook:CB81303953

Download	Molfile XML SDF

more structures >>

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19 18 0 0 0 0 999 V2000

4.0728 -1.4069 -2.0892 C 0 0 0 0 0 0 0 0 0 0 0 0

3.1369 0.7590 -1.1624 C 0 0 0 0 0 0 0 0 0 0 0 0

1.0000 -1.5008 -0.0387 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8639 -0.7130 -1.4833 C 0 0 2 0 0 0 0 0 0 0 0 0

2.3486 -1.4278 -0.3429 N 0 0 0 0 0 0 0 0 0 0 0 0

4.4840 -2.4832 -1.3778 O 0 0 0 0 0 0 0 0 0 0 0 0

4.6191 -1.0434 -3.1232 O 0 0 0 0 0 0 0 0 0 0 0 0

0.0846 -0.9883 -0.6712 O 0 0 0 0 0 0 0 0 0 0 0 0

0.6938 -2.2952 1.1879 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5014 1.0118 0.0209 S 0 0 0 0 0 0 0 0 0 0 0 0

3.0089 -1.9017 0.2691 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0715 -0.7684 -2.2404 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2418 1.2175 -0.7298 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3840 1.3107 -2.0755 H 0 0 0 0 0 0 0 0 0 0 0 0

5.2575 -2.9224 -1.7916 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1685 -1.7013 1.9535 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0320 -3.1514 0.9793 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5681 -2.7239 1.7034 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8986 -0.2673 0.0417 H 0 0 0 0 0 0 0 0 0 0 0 0

1 4 1 0 0 0 0

1 6 1 0 0 0 0

1 7 2 0 0 0 0

2 4 1 0 0 0 0

2 10 1 0 0 0 0

2 13 1 0 0 0 0

2 14 1 0 0 0 0

3 5 1 0 0 0 0

3 8 2 0 0 0 0

3 9 1 0 0 0 0

4 5 1 0 0 0 0

4 12 1 0 0 0 0

5 11 1 0 0 0 0

6 15 1 0 0 0 0

9 16 1 0 0 0 0

9 17 1 0 0 0 0

9 18 1 0 0 0 0

10 19 1 0 0 0 0

M END): 16 ms

reading 19 atoms

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Wikipedia	License
Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway.
Read full article at Wikipedia

Formula

C5H9NO3S

Net Charge

Average Mass

163.19590

Monoisotopic Mass

163.03031

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:txid9606)	See: DOI
Homo sapiens (NCBI:txid9606)	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. 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. ferroptosis inhibitor Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. 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 ferroptosis inhibitor (CHEBI:173084) N-acetyl-L-cysteine (CHEBI:28939) has role geroprotector (CHEBI:176497) 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) N-acetyl-L-cysteinyl residue (CHEBI:133372) is substituent group from 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

Manual Xrefs	Databases
66	DrugCentral
Acetylcysteine	Wikipedia
C06809	KEGG COMPOUND
CPD-9175	MetaCyc
D00221	KEGG DRUG
DB06151	DrugBank
HMDB0001890	HMDB
LSM-4672	LINCS
SC2	PDBeChem
View more database links

Registry Numbers	Types	Sources
142554	Gmelin Registry Number	Gmelin
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	Types	Sources
10651166	PubMed citation	Europe PMC
11544433	PubMed citation	Europe PMC
12057717	PubMed citation	Europe PMC
15025780	PubMed citation	Europe PMC
15647642	PubMed citation	Europe PMC
17174578	PubMed citation	Europe PMC
19580823	PubMed citation	Europe PMC
2026726	PubMed citation	Europe PMC
20819793	PubMed citation	Europe PMC
24119926	PubMed citation	Europe PMC
25553484	PubMed citation	Europe PMC
9624310	PubMed citation	Europe PMC
9711192	PubMed citation	Europe PMC

Last Modified

28 October 2021

CHEBI:28939 - N-acetyl-L-cysteine

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