Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2018-05-28 23:07:50 UTC
Primary IDFDB002281
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetyl-L-cysteine
DescriptionEffective 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 Number616-91-1
Structure
Thumb
Synonyms
SynonymSource
(2R)-2-acetylamino-3-Sulfanylpropanoic acidChEBI
(R)-2-acetylamino-3-Mercaptopropanoic acidChEBI
(R)-Mercapturic acidChEBI
AcetilcisteinaChEBI
AcetylcysteinumChEBI
L-AcetylcysteineChEBI
L-alpha-acetamido-beta-Mercaptopropionic acidChEBI
Mercapturic acidChEBI
N-Acetyl-L-(+)-cysteineChEBI
N-AcetylcysteineChEBI
NACChEBI
(2R)-2-acetylamino-3-SulfanylpropanoateGenerator
(2R)-2-acetylamino-3-SulphanylpropanoateGenerator
(2R)-2-acetylamino-3-Sulphanylpropanoic acidGenerator
(R)-2-acetylamino-3-MercaptopropanoateGenerator
(R)-MercaptateGenerator
(R)-Mercaptic acidGenerator
L-a-acetamido-b-MercaptopropionateGenerator
L-a-acetamido-b-Mercaptopropionic acidGenerator
L-alpha-acetamido-beta-MercaptopropionateGenerator
L-α-acetamido-β-mercaptopropionateGenerator
L-α-acetamido-β-mercaptopropionic acidGenerator
MercaptateGenerator
Mercaptic acidGenerator
AcetadoteHMDB
FlumucetinHMDB
2-acetylamino-3-mercapto-PropionateHMDB
2-acetylamino-3-mercapto-Propionic acidHMDB
Fluimicil infantilHMDB
FluimucetinHMDB
FluprowitHMDB
N-Acety-L-cysteineHMDB
N-Acetyl-3-mercaptoalanineHMDB
Sodium 2-acetamido-3-mercaptopropionateHMDB
AcemucMeSH
Acetylcysteine alcon brandMeSH
Acetylcysteine betapharm brandMeSH
Acetylcysteine bouchara brandMeSH
Acetylcysteine farmasan brandMeSH
Acetylcysteine fresenius brandMeSH
Acetylcysteine inpharzam brandMeSH
Acetylcysteine klinge brandMeSH
Acetylcysteine lindopharm brandMeSH
Acetylcysteine pharbita brandMeSH
Acetylcysteine whitehall brandMeSH
Acetylcysteine, monosodium saltMeSH
Acétylcystéine GNRMeSH
Allen and hanburys brand OF acetylcysteineMeSH
Bioiberica brand OF acetylcysteineMeSH
Bristol myers squibb brand OF acetylcysteineMeSH
BromucMeSH
Dey brand OF acetylcysteine sodium saltMeSH
EurespiranMeSH
ExomucMeSH
Fresenius brand OF acetylcysteineMeSH
GNR Pharma brand OF acetylcysteineMeSH
GNR-Pharma brand OF acetylcysteineMeSH
GenacMeSH
Génévrier brand OF acetylcysteineMeSH
Hermes brand OF acetylcysteineMeSH
Heumann brand OF acetylcysteineMeSH
Monosodium salt acetylcysteineMeSH
MucosilMeSH
NAC alMeSH
NAC, bisolvonMeSH
Oberlin brand OF acetylcysteineMeSH
Pfleger brand OF acetylcysteineMeSH
Produpharm lappe brand OF acetylcysteineMeSH
Roberts brand OF acetylcysteineMeSH
Roche nicholas brand OF acetylcysteineMeSH
SiranMeSH
Sodium, acetylcysteineMeSH
Temmler brand OF acetylcysteineMeSH
Teva brand OF acetylcysteineMeSH
Zambon brand OF acetylcysteineMeSH
Zambon, nacMeSH
Acetylcystein atidMeSH
Acetylcystein, mentopinMeSH
Acetylcysteine azupharma brandMeSH
Acetylcysteine centrafarm brandMeSH
Acetylcysteine hermes brandMeSH
Acetylcysteine krewel brandMeSH
Acetylcysteine temmler brandMeSH
Acetylcysteine teva brandMeSH
Acetylcysteine upsa brandMeSH
Acetylcysteine zyma brandMeSH
Acetylcysteine, (DL)-isomerMeSH
Betapharm brand OF acetylcysteineMeSH
Bristol myers squibb brand OF acetylcysteine sodium saltMeSH
Disphar brand OF acetylcysteineMeSH
Farmasan brand OF acetylcysteineMeSH
FluimucilMeSH
JenapharmMeSH
Klinge brand OF acetylcysteineMeSH
Lindopharm brand OF acetylcysteineMeSH
MPectilMeSH
Merck brand OF acetylcysteineMeSH
MucosolMeSH
NAC zambonMeSH
SiccoralMeSH
Trommsdorff brand OF acetylcysteineMeSH
Zyma brand OF acetylcysteineMeSH
Mentopin acetylcysteinMeSH
Acetylcystein alMeSH
Acetylcystein heumannMeSH
Acetylcystein tromMeSH
Acetylcysteine aluid brandMeSH
Acetylcysteine disphar brandMeSH
Acetylcysteine GNR-pharma brandMeSH
Acetylcysteine lichtenstein brandMeSH
Acetylcysteine merck brandMeSH
Acetylcysteine oberlin brandMeSH
Acetylcysteine roberts brandMeSH
Acetylcysteine sodiumMeSH
Acetylcysteine thiemann brandMeSH
Acetylcysteine zincMeSH
Acetylcysteine, monoammonium saltMeSH
AcetystMeSH
Acid, mercapturicMeSH
AirbronMeSH
Alcon brand OF acetylcysteineMeSH
Aluid brand OF acetylcysteineMeSH
AlveolexMeSH
Atid brand OF acetylcysteineMeSH
AzubronchinMeSH
Boehringer ingelheim brand OF acetylcysteineMeSH
Bristol-myers squibb brand OF acetylcysteine sodium saltMeSH
broncho FipsMeSH
BroncholysinMeSH
Centrafarm brand OF acetylcysteineMeSH
CodotussylMeSH
CystamucilMeSH
dampo MucopectMeSH
HoestilMeSH
Hustengetränk, optipectMeSH
Inpharzam brand OF acetylcysteineMeSH
Intra brand OF acetylcysteineMeSH
Larylin nacMeSH
LindocetylMeSH
m PectilMeSH
Mucopect, dampoMeSH
MucosolvinMeSH
Optipect hustengetränkMeSH
Sanigen, mucoMeSH
SolmucolMeSH
Thiemann brand OF acetylcysteineMeSH
Whitehall brand OF acetylcysteineMeSH
Zinc, acetylcysteineMeSH
AcebrausMeSH
DurabronchalMeSH
AcetabsMeSH
Acetylcysteine atid brandMeSH
Acetylcysteine bioiberica brandMeSH
Acetylcysteine guerbet brandMeSH
Acetylcysteine génévrier brandMeSH
Acetylcysteine heumann brandMeSH
Acetylcysteine hydrochlorideMeSH
Acetylcysteine intra brandMeSH
Acetylcysteine pfleger brandMeSH
Acetylcysteine trommsdorff brandMeSH
Acetylcysteine zambon brandMeSH
Acetylcysteine ac-pharma brandMeSH
Acetylcysteine, (D)-isomerMeSH
AcetylinMeSH
Azupharma brand OF acetylcysteineMeSH
Bisolvon nacMeSH
Bouchara brand OF acetylcysteineMeSH
Bristol-myers squibb brand OF acetylcysteineMeSH
broncho-FipsMeSH
BronchoFipsMeSH
BroncoclarMeSH
FabrolMeSH
FrekatussMeSH
Guerbet brand OF acetylcysteineMeSH
Hydrochloride, acetylcysteineMeSH
IlubeMeSH
JenacysteinMeSH
Krewel brand OF acetylcysteineMeSH
LantamedMeSH
Lichtenstein brand OF acetylcysteineMeSH
m-PectilMeSH
Monoammonium salt acetylcysteineMeSH
MuciteranMeSH
muco SanigenMeSH
MucomystMeSH
N Acetyl L cysteineMeSH
N AcetylcysteineMeSH
Pharbita brand OF acetylcysteineMeSH
UPSA brand OF acetylcysteineMeSH
Ac pharma brand OF acetylcysteineMeSH
Ac-pharma brand OF acetylcysteineMeSH
(2R)-2-(Acetylamino)-3-mercaptopropanoic acidbiospider
(2R)-2-Acetamido-3-sulfanyl-propanoic acidbiospider
(2R)-2-Acetylamino-3-sulfanylpropanoic acidbiospider
(R)-2-Acetylamino-3-mercaptopropanoic acidbiospider
2-Acetylamino-3-mercapto-propionatebiospider
2-Acetylamino-3-mercapto-propionic acidbiospider
Aceteinbiospider
Acetylcysteinemanual
L-2-Acetamido-3-mercaptopropanoic acidmanual
L-alpha-Acetamido-beta-mercaptopropionic acidbiospider
Lysomucilbiospider
N-Acetyl cysteinebiospider
N-Acetyl-L-cysteinebiospider
N-Acetylcysteine; L-formdb_source
NSC 111180db_source
Parvolexdb_source
Respairedb_source
Predicted Properties
PropertyValueSource
Water Solubility5.09 g/LALOGPS
logP-0.03ALOGPS
logP-0.71ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.67 m³·mol⁻¹ChemAxon
Polarizability15.34 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H9NO3S
IUPAC name(2R)-2-acetamido-3-sulfanylpropanoic acid
InChI IdentifierInChI=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 KeyPWKSKIMOESPYIA-BYPYZUCNSA-N
Isomeric SMILESCC(=O)N[C@@H](CS)C(O)=O
Average Molecular Weight163.195
Monoisotopic Molecular Weight163.030313849
Classification
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 36.80%; H 5.56%; N 8.58%; O 29.41%; S 19.65%DFC
Melting PointMp 109-110°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKa9.52
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +5 (c, 3 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0i00-2970000000-d817070e3a42f5e63ec5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ox-9000000000-192b8907b32f1e180c72View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0i00-2970000000-d817070e3a42f5e63ec5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-13c710ac0e0547e1ec40View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0100-9400000000-f5d15a7328f8eeae70feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-b0d92bfcc2536077a6fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-f305286cee84e6ae992bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-9000000000-b10b4a2a6383336db871View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-1900000000-1fd4ac48c9f822eb3500View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-6900000000-d0c51a69ac11096d05c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-218fead85424144539bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-55d7f2c18d3e85caad05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01zi-6900000000-ceec8ba29592de7e4362View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9200000000-fca1bad01b5fff79588bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID11540
ChEMBL IDCHEMBL600
KEGG Compound IDC06809
Pubchem Compound ID12035
Pubchem Substance IDNot Available
ChEBI ID28939
Phenol-Explorer IDNot Available
DrugBank IDDB06151
HMDB IDHMDB01890
CRC / DFC (Dictionary of Food Compounds) IDCJK78-F:CJK79-G
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID1ZT
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAcetylcysteine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference