Showing Compound N-Acetyl-L-cysteine (FDB002281)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:18 UTC

Update date

2018-05-28 23:07:50 UTC

Primary ID

FDB002281

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Acetyl-L-cysteine

Description

Effective inhibitor of enzymic browning in foods [DFC] N-Acetyl-L-cysteine is a pharmaceutical drug and nutritional supplement used primarily as a mucolytic agent and in the management of paracetamol (acetaminophen) overdose. Other uses include sulfate repletion in conditions, such as autism, where cysteine and related sulfur amino acids may be depleted. N-Acetyl-L-cysteine is a precursor in the formation of the antioxidant glutathione in the body. The thiol group confers antioxidant effects and is able to reduce free radicals. [Wikipedia].

CAS Number

616-91-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	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
N-Acety-L-cysteine	HMDB
N-Acetyl-3-mercaptoalanine	HMDB
Sodium 2-acetamido-3-mercaptopropionate	HMDB
Acemuc	MeSH
Acetylcysteine alcon brand	MeSH
Acetylcysteine betapharm brand	MeSH
Acetylcysteine bouchara brand	MeSH
Acetylcysteine farmasan brand	MeSH
Acetylcysteine fresenius brand	MeSH
Acetylcysteine inpharzam brand	MeSH
Acetylcysteine klinge brand	MeSH
Acetylcysteine lindopharm brand	MeSH
Acetylcysteine pharbita brand	MeSH
Acetylcysteine whitehall brand	MeSH
Acetylcysteine, monosodium salt	MeSH
Acétylcystéine GNR	MeSH
Allen and hanburys brand OF acetylcysteine	MeSH
Bioiberica brand OF acetylcysteine	MeSH
Bristol myers squibb brand OF acetylcysteine	MeSH
Bromuc	MeSH
Dey brand OF acetylcysteine sodium salt	MeSH
Eurespiran	MeSH
Exomuc	MeSH
Fresenius brand OF acetylcysteine	MeSH
GNR Pharma brand OF acetylcysteine	MeSH
GNR-Pharma brand OF acetylcysteine	MeSH
Genac	MeSH
Génévrier brand OF acetylcysteine	MeSH
Hermes brand OF acetylcysteine	MeSH
Heumann brand OF acetylcysteine	MeSH
Monosodium salt acetylcysteine	MeSH
Mucosil	MeSH
NAC al	MeSH
NAC, bisolvon	MeSH
Oberlin brand OF acetylcysteine	MeSH
Pfleger brand OF acetylcysteine	MeSH
Produpharm lappe brand OF acetylcysteine	MeSH
Roberts brand OF acetylcysteine	MeSH
Roche nicholas brand OF acetylcysteine	MeSH
Siran	MeSH
Sodium, acetylcysteine	MeSH
Temmler brand OF acetylcysteine	MeSH
Teva brand OF acetylcysteine	MeSH
Zambon brand OF acetylcysteine	MeSH
Zambon, nac	MeSH
Acetylcystein atid	MeSH
Acetylcystein, mentopin	MeSH
Acetylcysteine azupharma brand	MeSH
Acetylcysteine centrafarm brand	MeSH
Acetylcysteine hermes brand	MeSH
Acetylcysteine krewel brand	MeSH
Acetylcysteine temmler brand	MeSH
Acetylcysteine teva brand	MeSH
Acetylcysteine upsa brand	MeSH
Acetylcysteine zyma brand	MeSH
Acetylcysteine, (DL)-isomer	MeSH
Betapharm brand OF acetylcysteine	MeSH
Bristol myers squibb brand OF acetylcysteine sodium salt	MeSH
Disphar brand OF acetylcysteine	MeSH
Farmasan brand OF acetylcysteine	MeSH
Fluimucil	MeSH
Jenapharm	MeSH
Klinge brand OF acetylcysteine	MeSH
Lindopharm brand OF acetylcysteine	MeSH
MPectil	MeSH
Merck brand OF acetylcysteine	MeSH
Mucosol	MeSH
NAC zambon	MeSH
Siccoral	MeSH
Trommsdorff brand OF acetylcysteine	MeSH
Zyma brand OF acetylcysteine	MeSH
Mentopin acetylcystein	MeSH
Acetylcystein al	MeSH
Acetylcystein heumann	MeSH
Acetylcystein trom	MeSH
Acetylcysteine aluid brand	MeSH
Acetylcysteine disphar brand	MeSH
Acetylcysteine GNR-pharma brand	MeSH
Acetylcysteine lichtenstein brand	MeSH
Acetylcysteine merck brand	MeSH
Acetylcysteine oberlin brand	MeSH
Acetylcysteine roberts brand	MeSH
Acetylcysteine sodium	MeSH
Acetylcysteine thiemann brand	MeSH
Acetylcysteine zinc	MeSH
Acetylcysteine, monoammonium salt	MeSH
Acetyst	MeSH
Acid, mercapturic	MeSH
Airbron	MeSH
Alcon brand OF acetylcysteine	MeSH
Aluid brand OF acetylcysteine	MeSH
Alveolex	MeSH
Atid brand OF acetylcysteine	MeSH
Azubronchin	MeSH
Boehringer ingelheim brand OF acetylcysteine	MeSH
Bristol-myers squibb brand OF acetylcysteine sodium salt	MeSH
broncho Fips	MeSH
Broncholysin	MeSH
Centrafarm brand OF acetylcysteine	MeSH
Codotussyl	MeSH
Cystamucil	MeSH
dampo Mucopect	MeSH
Hoestil	MeSH
Hustengetränk, optipect	MeSH
Inpharzam brand OF acetylcysteine	MeSH
Intra brand OF acetylcysteine	MeSH
Larylin nac	MeSH
Lindocetyl	MeSH
m Pectil	MeSH
Mucopect, dampo	MeSH
Mucosolvin	MeSH
Optipect hustengetränk	MeSH
Sanigen, muco	MeSH
Solmucol	MeSH
Thiemann brand OF acetylcysteine	MeSH
Whitehall brand OF acetylcysteine	MeSH
Zinc, acetylcysteine	MeSH
Acebraus	MeSH
Durabronchal	MeSH
Acetabs	MeSH
Acetylcysteine atid brand	MeSH
Acetylcysteine bioiberica brand	MeSH
Acetylcysteine guerbet brand	MeSH
Acetylcysteine génévrier brand	MeSH
Acetylcysteine heumann brand	MeSH
Acetylcysteine hydrochloride	MeSH
Acetylcysteine intra brand	MeSH
Acetylcysteine pfleger brand	MeSH
Acetylcysteine trommsdorff brand	MeSH
Acetylcysteine zambon brand	MeSH
Acetylcysteine ac-pharma brand	MeSH
Acetylcysteine, (D)-isomer	MeSH
Acetylin	MeSH
Azupharma brand OF acetylcysteine	MeSH
Bisolvon nac	MeSH
Bouchara brand OF acetylcysteine	MeSH
Bristol-myers squibb brand OF acetylcysteine	MeSH
broncho-Fips	MeSH
BronchoFips	MeSH
Broncoclar	MeSH
Fabrol	MeSH
Frekatuss	MeSH
Guerbet brand OF acetylcysteine	MeSH
Hydrochloride, acetylcysteine	MeSH
Ilube	MeSH
Jenacystein	MeSH
Krewel brand OF acetylcysteine	MeSH
Lantamed	MeSH
Lichtenstein brand OF acetylcysteine	MeSH
m-Pectil	MeSH
Monoammonium salt acetylcysteine	MeSH
Muciteran	MeSH
muco Sanigen	MeSH
Mucomyst	MeSH
N Acetyl L cysteine	MeSH
N Acetylcysteine	MeSH
Pharbita brand OF acetylcysteine	MeSH
UPSA brand OF acetylcysteine	MeSH
Ac pharma brand OF acetylcysteine	MeSH
Ac-pharma brand OF acetylcysteine	MeSH
(2R)-2-(Acetylamino)-3-mercaptopropanoic acid	biospider
(2R)-2-Acetamido-3-sulfanyl-propanoic acid	biospider
(2R)-2-Acetylamino-3-sulfanylpropanoic acid	biospider
(R)-2-Acetylamino-3-mercaptopropanoic acid	biospider
2-Acetylamino-3-mercapto-propionate	biospider
2-Acetylamino-3-mercapto-propionic acid	biospider
Acetein	biospider
Acetylcysteine	manual
L-2-Acetamido-3-mercaptopropanoic acid	manual
L-alpha-Acetamido-beta-mercaptopropionic acid	biospider
Lysomucil	biospider
N-Acetyl cysteine	biospider
N-Acetyl-L-cysteine	biospider
N-Acetylcysteine; L-form	db_source
NSC 111180	db_source
Parvolex	db_source
Respaire	db_source

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)	-1.5	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C5H9NO3S

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

163.195

Monoisotopic Molecular Weight

163.030313849

Classification

Description

This compound 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 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 36.80%; H 5.56%; N 8.58%; O 29.41%; S 19.65%	DFC
Melting Point	Mp 109-110°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	9.52
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +5 (c, 3 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0i00-2970000000-d817070e3a42f5e63ec5	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ox-9000000000-192b8907b32f1e180c72	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0i00-2970000000-d817070e3a42f5e63ec5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-13c710ac0e0547e1ec40	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0100-9400000000-f5d15a7328f8eeae70fe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-b0d92bfcc2536077a6fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-f305286cee84e6ae992b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-b10b4a2a6383336db871	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-1900000000-1fd4ac48c9f822eb3500	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6900000000-d0c51a69ac11096d05c3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-218fead85424144539bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-55d7f2c18d3e85caad05	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01zi-6900000000-ceec8ba29592de7e4362	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9200000000-fca1bad01b5fff79588b	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer