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

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