ChemFOnt: Showing chemical card for Acetylcysteine (CFc000001258)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:51 UTC

Chemfont ID

CFc000001258

Molecule Identification

Common Name

Acetylcysteine

Definition

N-Acetyl-L-cysteine (NAC) or N-Acetylcysteine is the N-acetyl derivative of the amino acid L-cysteine and is a precursor in the formation of the antioxidant glutathione in the body. N-Acetylcysteine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-L-cysteine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-cysteine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-cysteine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. . N-acetylated amino acids, such as N-acetylcysteine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free cysteine can also occur. The enzyme known as cysteine-S-conjugate N-acetyltransferase (EC 2.3.1.80) catalyzes the transfer of the acetyl group of acetyl CoA to the amino group of cysteine. This enzyme is an important participant in glutathione metabolism and the production of glutathione. The thiol (sulfhydryl) group in N-Acetylcysteine confers antioxidant effects and is able to reduce free radicals. N-Acetylcysteine is a pharmacological agent used in the management of paracetamol (acetaminophen) overdoses. When acetaminophen is taken in large quantities, a minor metabolite called N-acetyl-p-benzoquinone imine (NAPQI) accumulates within the body. NAPQI is normally conjugated by glutathione, but when taken in excess, the body's glutathione reserves are not sufficient to deactivate the toxic NAPQI. In the treatment of acetaminophen overdose, N-acetylcysteine acts to maintain or replenish depleted glutathione reserves in the liver and enhance non-toxic metabolism of acetaminophen. These actions serve to protect liver cells from NAPQI toxicity. For this particular indication, N-acetylcysteine is available under the trade names Mucomyst (Bristol-Myers Squibb) and Parvolex (GSK). N-Acetylcysteine is also used as a mucolytic agent to reduce the viscosity of mucous secretions. It has also been shown to have antiviral effects in patients with HIV due to inhibition of viral stimulation by reactive oxygen intermediates. Acetylcysteine has been studied for a number of psychiatric disorders. There is tentative evidence for N-acetylcysteine being useful in the treatment of Alzheimer's disease, autism, bipolar disorder, drug-induced neuropathy, major depressive disorder, obsessive-compulsive disorder, and schizophrenia (PMID: 21118657 ). Many N-acetylamino acids, including N-acetylcysteine, can act as uremic toxins if present in high abundance in the serum or plasma (PMID: 21970774 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Acetylamino-3-sulfanylpropanoic acid	ChEBI
(R)-2-Acetylamino-3-mercaptopropanoic acid	ChEBI
(R)-Mercapturic acid	ChEBI
Acetilcisteina	ChEBI
Acetylcysteinum	ChEBI
L-Acetylcysteine	ChEBI
L-alpha-Acetamido-beta-mercaptopropionic acid	ChEBI
Mercapturic acid	ChEBI
N-Acetyl-L-(+)-cysteine	ChEBI
N-Acetylcysteine	ChEBI
NAC	ChEBI
(2R)-2-Acetylamino-3-sulfanylpropanoate	Generator
(2R)-2-Acetylamino-3-sulphanylpropanoate	Generator
(2R)-2-Acetylamino-3-sulphanylpropanoic acid	Generator
(R)-2-Acetylamino-3-mercaptopropanoate	Generator
(R)-Mercaptate	Generator
(R)-Mercaptic acid	Generator
L-a-Acetamido-b-mercaptopropionate	Generator
L-a-Acetamido-b-mercaptopropionic acid	Generator
L-alpha-Acetamido-beta-mercaptopropionate	Generator
L-Α-acetamido-β-mercaptopropionate	Generator
L-Α-acetamido-β-mercaptopropionic acid	Generator
Mercaptate	Generator
Mercaptic acid	Generator
Acetadote	HMDB
Flumucetin	HMDB
2-acetylamino-3-mercapto-Propionate	HMDB
2-acetylamino-3-mercapto-Propionic acid	HMDB
Fluimicil infantil	HMDB
Fluimucetin	HMDB
Fluprowit	HMDB, MeSH
N-Acety-L-cysteine	HMDB
N-Acetyl-3-mercaptoalanine	HMDB
Sodium 2-acetamido-3-mercaptopropionate	HMDB
Acemuc	MeSH, HMDB
Acetylcysteine alcon brand	MeSH, HMDB
Acetylcysteine betapharm brand	MeSH, HMDB
Acetylcysteine bouchara brand	MeSH, HMDB
Acetylcysteine farmasan brand	MeSH, HMDB
Acetylcysteine fresenius brand	MeSH, HMDB
Acetylcysteine inpharzam brand	MeSH, HMDB
Acetylcysteine klinge brand	MeSH, HMDB
Acetylcysteine lindopharm brand	MeSH, HMDB
Acetylcysteine pharbita brand	MeSH, HMDB
Acetylcysteine whitehall brand	MeSH, HMDB
Acetylcysteine, monosodium salt	MeSH, HMDB
Acétylcystéine GNR	MeSH, HMDB
Allen and hanburys brand OF acetylcysteine	MeSH, HMDB
Bioiberica brand OF acetylcysteine	MeSH, HMDB
Bristol myers squibb brand OF acetylcysteine	MeSH, HMDB
Bromuc	MeSH, HMDB
Dey brand OF acetylcysteine sodium salt	MeSH, HMDB
Eurespiran	MeSH, HMDB
Exomuc	MeSH, HMDB
Fresenius brand OF acetylcysteine	MeSH, HMDB
GNR Pharma brand OF acetylcysteine	MeSH, HMDB
GNR-Pharma brand OF acetylcysteine	MeSH, HMDB
Genac	MeSH, HMDB
Génévrier brand OF acetylcysteine	MeSH, HMDB
Hermes brand OF acetylcysteine	MeSH, HMDB
Heumann brand OF acetylcysteine	MeSH, HMDB
Monosodium salt acetylcysteine	MeSH, HMDB
Mucosil	MeSH, HMDB
NAC al	MeSH, HMDB
NAC, bisolvon	MeSH, HMDB
Oberlin brand OF acetylcysteine	MeSH, HMDB
Pfleger brand OF acetylcysteine	MeSH, HMDB
Produpharm lappe brand OF acetylcysteine	MeSH, HMDB
Roberts brand OF acetylcysteine	MeSH, HMDB
Roche nicholas brand OF acetylcysteine	MeSH, HMDB
Siran	MeSH, HMDB
Sodium, acetylcysteine	MeSH, HMDB
Temmler brand OF acetylcysteine	MeSH, HMDB
Teva brand OF acetylcysteine	MeSH, HMDB
Zambon brand OF acetylcysteine	MeSH, HMDB
Zambon, nac	MeSH, HMDB
Acetylcystein atid	MeSH, HMDB
Acetylcystein, mentopin	MeSH, HMDB
Acetylcysteine azupharma brand	MeSH, HMDB
Acetylcysteine centrafarm brand	MeSH, HMDB
Acetylcysteine hermes brand	MeSH, HMDB
Acetylcysteine krewel brand	MeSH, HMDB
Acetylcysteine temmler brand	MeSH, HMDB
Acetylcysteine teva brand	MeSH, HMDB
Acetylcysteine upsa brand	MeSH, HMDB
Acetylcysteine zyma brand	MeSH, HMDB
Acetylcysteine, (DL)-isomer	MeSH, HMDB
Betapharm brand OF acetylcysteine	MeSH, HMDB
Bristol myers squibb brand OF acetylcysteine sodium salt	MeSH, HMDB
Disphar brand OF acetylcysteine	MeSH, HMDB
Farmasan brand OF acetylcysteine	MeSH, HMDB
Fluimucil	MeSH, HMDB
Jenapharm	MeSH, HMDB
Klinge brand OF acetylcysteine	MeSH, HMDB
Lindopharm brand OF acetylcysteine	MeSH, HMDB
MPectil	MeSH, HMDB
Merck brand OF acetylcysteine	MeSH, HMDB
Mucosol	MeSH, HMDB
NAC zambon	MeSH, HMDB
Siccoral	MeSH, HMDB
Trommsdorff brand OF acetylcysteine	MeSH, HMDB
Zyma brand OF acetylcysteine	MeSH, HMDB
Mentopin acetylcystein	MeSH, HMDB
Acetylcystein al	MeSH, HMDB
Acetylcystein heumann	MeSH, HMDB
Acetylcystein trom	MeSH, HMDB
Acetylcysteine aluid brand	MeSH, HMDB
Acetylcysteine disphar brand	MeSH, HMDB
Acetylcysteine GNR-pharma brand	MeSH, HMDB
Acetylcysteine lichtenstein brand	MeSH, HMDB
Acetylcysteine merck brand	MeSH, HMDB
Acetylcysteine oberlin brand	MeSH, HMDB
Acetylcysteine roberts brand	MeSH, HMDB
Acetylcysteine sodium	MeSH, HMDB
Acetylcysteine thiemann brand	MeSH, HMDB
Acetylcysteine zinc	MeSH, HMDB
Acetylcysteine, monoammonium salt	MeSH, HMDB
Acetyst	MeSH, HMDB
Acid, mercapturic	MeSH, HMDB
Airbron	MeSH, HMDB
Alcon brand OF acetylcysteine	MeSH, HMDB
Aluid brand OF acetylcysteine	MeSH, HMDB
Alveolex	MeSH, HMDB
Atid brand OF acetylcysteine	MeSH, HMDB
Azubronchin	MeSH, HMDB
Boehringer ingelheim brand OF acetylcysteine	MeSH, HMDB
Bristol-myers squibb brand OF acetylcysteine sodium salt	MeSH, HMDB
broncho Fips	MeSH, HMDB
Broncholysin	MeSH, HMDB
Centrafarm brand OF acetylcysteine	MeSH, HMDB
Codotussyl	MeSH, HMDB
Cystamucil	MeSH, HMDB
dampo Mucopect	MeSH, HMDB
Hoestil	MeSH, HMDB
Hustengetränk, optipect	MeSH, HMDB
Inpharzam brand OF acetylcysteine	MeSH, HMDB
Intra brand OF acetylcysteine	MeSH, HMDB
Larylin nac	MeSH, HMDB
Lindocetyl	MeSH, HMDB
m Pectil	MeSH, HMDB
Mucopect, dampo	MeSH, HMDB
Mucosolvin	MeSH, HMDB
Optipect hustengetränk	MeSH, HMDB
Sanigen, muco	MeSH, HMDB
Solmucol	MeSH, HMDB
Thiemann brand OF acetylcysteine	MeSH, HMDB
Whitehall brand OF acetylcysteine	MeSH, HMDB
Zinc, acetylcysteine	MeSH, HMDB
Acebraus	MeSH, HMDB
Durabronchal	MeSH, HMDB
Acetabs	MeSH, HMDB
Acetylcysteine atid brand	MeSH, HMDB
Acetylcysteine bioiberica brand	MeSH, HMDB
Acetylcysteine guerbet brand	MeSH, HMDB
Acetylcysteine génévrier brand	MeSH, HMDB
Acetylcysteine heumann brand	MeSH, HMDB
Acetylcysteine hydrochloride	MeSH, HMDB
Acetylcysteine intra brand	MeSH, HMDB
Acetylcysteine pfleger brand	MeSH, HMDB
Acetylcysteine trommsdorff brand	MeSH, HMDB
Acetylcysteine zambon brand	MeSH, HMDB
Acetylcysteine ac-pharma brand	MeSH, HMDB
Acetylcysteine, (D)-isomer	MeSH, HMDB
Acetylin	MeSH, HMDB
Azupharma brand OF acetylcysteine	MeSH, HMDB
Bisolvon nac	MeSH, HMDB
Bouchara brand OF acetylcysteine	MeSH, HMDB
Bristol-myers squibb brand OF acetylcysteine	MeSH, HMDB
broncho-Fips	MeSH, HMDB
BronchoFips	MeSH, HMDB
Broncoclar	MeSH, HMDB
Fabrol	MeSH, HMDB
Frekatuss	MeSH, HMDB
Guerbet brand OF acetylcysteine	MeSH, HMDB
Hydrochloride, acetylcysteine	MeSH, HMDB
Ilube	MeSH, HMDB
Jenacystein	MeSH, HMDB
Krewel brand OF acetylcysteine	MeSH, HMDB
Lantamed	MeSH, HMDB
Lichtenstein brand OF acetylcysteine	MeSH, HMDB
m-Pectil	MeSH, HMDB
Monoammonium salt acetylcysteine	MeSH, HMDB
Muciteran	MeSH, HMDB
muco Sanigen	MeSH, HMDB
Mucomyst	MeSH, HMDB
N Acetyl L cysteine	MeSH, HMDB
N Acetylcysteine	MeSH, HMDB
Pharbita brand OF acetylcysteine	MeSH, HMDB
UPSA brand OF acetylcysteine	MeSH, HMDB
Ac pharma brand OF acetylcysteine	MeSH, HMDB
Ac-pharma brand OF acetylcysteine	MeSH, HMDB
Acetylcysteine	ChEBI

Chemical Formula

C₅H₉NO₃S

Average Molecular Weight

163.195

Monoisotopic Molecular Weight

163.030313849

IUPAC Name

(2R)-2-acetamido-3-sulfanylpropanoic acid

Traditional Name

acetylcysteine

CAS Registry Number

616-91-1

SMILES

CC(=O)N[C@@H](CS)C(O)=O

InChI Identifier

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

InChI Key

PWKSKIMOESPYIA-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Alkylthiol
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-cysteine derivative (CHEBI:28939 )
N-acetyl-L-amino acid (CHEBI:28939 )
acetylcysteine (CHEBI:28939 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2026726)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001890)

Fibroblasts (HMDB: HMDB0001890)
Neuron (HMDB: HMDB0001890)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)
Feces (PMID: 27065191)

Cellular substructure

Cytoplasm (HMDB: HMDB0001890)
Myelin sheath (HMDB: HMDB0001890)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001890)

Source

Exogenous

Exogenous (HMDB: HMDB0001890)

Food

Food (HMDB: HMDB0001890)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Endogenous

Endogenous (HMDB: HMDB0001890)

Animal

Animal (HMDB: HMDB0001890)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001890)

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0001890)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.09 g/L	ALOGPS
logP	-0.03	ALOGPS
logP	-0.71	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	37.67 m³·mol⁻¹	ChemAxon
Polarizability	15.34 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon