Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2019-11-26 02:57:16 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, MeSH
N-Acety-L-cysteineHMDB
N-Acetyl-3-mercaptoalanineHMDB
Sodium 2-acetamido-3-mercaptopropionateHMDB
AcemucMeSH, HMDB
Acetylcysteine alcon brandMeSH, HMDB
Acetylcysteine betapharm brandMeSH, HMDB
Acetylcysteine bouchara brandMeSH, HMDB
Acetylcysteine farmasan brandMeSH, HMDB
Acetylcysteine fresenius brandMeSH, HMDB
Acetylcysteine inpharzam brandMeSH, HMDB
Acetylcysteine klinge brandMeSH, HMDB
Acetylcysteine lindopharm brandMeSH, HMDB
Acetylcysteine pharbita brandMeSH, HMDB
Acetylcysteine whitehall brandMeSH, HMDB
Acetylcysteine, monosodium saltMeSH, HMDB
Acétylcystéine GNRMeSH, HMDB
Allen and hanburys brand OF acetylcysteineMeSH, HMDB
Bioiberica brand OF acetylcysteineMeSH, HMDB
Bristol myers squibb brand OF acetylcysteineMeSH, HMDB
BromucMeSH, HMDB
Dey brand OF acetylcysteine sodium saltMeSH, HMDB
EurespiranMeSH, HMDB
ExomucMeSH, HMDB
Fresenius brand OF acetylcysteineMeSH, HMDB
GNR Pharma brand OF acetylcysteineMeSH, HMDB
GNR-Pharma brand OF acetylcysteineMeSH, HMDB
GenacMeSH, HMDB
Génévrier brand OF acetylcysteineMeSH, HMDB
Hermes brand OF acetylcysteineMeSH, HMDB
Heumann brand OF acetylcysteineMeSH, HMDB
Monosodium salt acetylcysteineMeSH, HMDB
MucosilMeSH, HMDB
NAC alMeSH, HMDB
NAC, bisolvonMeSH, HMDB
Oberlin brand OF acetylcysteineMeSH, HMDB
Pfleger brand OF acetylcysteineMeSH, HMDB
Produpharm lappe brand OF acetylcysteineMeSH, HMDB
Roberts brand OF acetylcysteineMeSH, HMDB
Roche nicholas brand OF acetylcysteineMeSH, HMDB
SiranMeSH, HMDB
Sodium, acetylcysteineMeSH, HMDB
Temmler brand OF acetylcysteineMeSH, HMDB
Teva brand OF acetylcysteineMeSH, HMDB
Zambon brand OF acetylcysteineMeSH, HMDB
Zambon, nacMeSH, HMDB
Acetylcystein atidMeSH, HMDB
Acetylcystein, mentopinMeSH, HMDB
Acetylcysteine azupharma brandMeSH, HMDB
Acetylcysteine centrafarm brandMeSH, HMDB
Acetylcysteine hermes brandMeSH, HMDB
Acetylcysteine krewel brandMeSH, HMDB
Acetylcysteine temmler brandMeSH, HMDB
Acetylcysteine teva brandMeSH, HMDB
Acetylcysteine upsa brandMeSH, HMDB
Acetylcysteine zyma brandMeSH, HMDB
Acetylcysteine, (DL)-isomerMeSH, HMDB
Betapharm brand OF acetylcysteineMeSH, HMDB
Bristol myers squibb brand OF acetylcysteine sodium saltMeSH, HMDB
Disphar brand OF acetylcysteineMeSH, HMDB
Farmasan brand OF acetylcysteineMeSH, HMDB
FluimucilMeSH, HMDB
JenapharmMeSH, HMDB
Klinge brand OF acetylcysteineMeSH, HMDB
Lindopharm brand OF acetylcysteineMeSH, HMDB
MPectilMeSH, HMDB
Merck brand OF acetylcysteineMeSH, HMDB
MucosolMeSH, HMDB
NAC zambonMeSH, HMDB
SiccoralMeSH, HMDB
Trommsdorff brand OF acetylcysteineMeSH, HMDB
Zyma brand OF acetylcysteineMeSH, HMDB
Mentopin acetylcysteinMeSH, HMDB
Acetylcystein alMeSH, HMDB
Acetylcystein heumannMeSH, HMDB
Acetylcystein tromMeSH, HMDB
Acetylcysteine aluid brandMeSH, HMDB
Acetylcysteine disphar brandMeSH, HMDB
Acetylcysteine GNR-pharma brandMeSH, HMDB
Acetylcysteine lichtenstein brandMeSH, HMDB
Acetylcysteine merck brandMeSH, HMDB
Acetylcysteine oberlin brandMeSH, HMDB
Acetylcysteine roberts brandMeSH, HMDB
Acetylcysteine sodiumMeSH, HMDB
Acetylcysteine thiemann brandMeSH, HMDB
Acetylcysteine zincMeSH, HMDB
Acetylcysteine, monoammonium saltMeSH, HMDB
AcetystMeSH, HMDB
Acid, mercapturicMeSH, HMDB
AirbronMeSH, HMDB
Alcon brand OF acetylcysteineMeSH, HMDB
Aluid brand OF acetylcysteineMeSH, HMDB
AlveolexMeSH, HMDB
Atid brand OF acetylcysteineMeSH, HMDB
AzubronchinMeSH, HMDB
Boehringer ingelheim brand OF acetylcysteineMeSH, HMDB
Bristol-myers squibb brand OF acetylcysteine sodium saltMeSH, HMDB
broncho FipsMeSH, HMDB
BroncholysinMeSH, HMDB
Centrafarm brand OF acetylcysteineMeSH, HMDB
CodotussylMeSH, HMDB
CystamucilMeSH, HMDB
dampo MucopectMeSH, HMDB
HoestilMeSH, HMDB
Hustengetränk, optipectMeSH, HMDB
Inpharzam brand OF acetylcysteineMeSH, HMDB
Intra brand OF acetylcysteineMeSH, HMDB
Larylin nacMeSH, HMDB
LindocetylMeSH, HMDB
m PectilMeSH, HMDB
Mucopect, dampoMeSH, HMDB
MucosolvinMeSH, HMDB
Optipect hustengetränkMeSH, HMDB
Sanigen, mucoMeSH, HMDB
SolmucolMeSH, HMDB
Thiemann brand OF acetylcysteineMeSH, HMDB
Whitehall brand OF acetylcysteineMeSH, HMDB
Zinc, acetylcysteineMeSH, HMDB
AcebrausMeSH, HMDB
DurabronchalMeSH, HMDB
AcetabsMeSH, HMDB
Acetylcysteine atid brandMeSH, HMDB
Acetylcysteine bioiberica brandMeSH, HMDB
Acetylcysteine guerbet brandMeSH, HMDB
Acetylcysteine génévrier brandMeSH, HMDB
Acetylcysteine heumann brandMeSH, HMDB
Acetylcysteine hydrochlorideMeSH, HMDB
Acetylcysteine intra brandMeSH, HMDB
Acetylcysteine pfleger brandMeSH, HMDB
Acetylcysteine trommsdorff brandMeSH, HMDB
Acetylcysteine zambon brandMeSH, HMDB
Acetylcysteine ac-pharma brandMeSH, HMDB
Acetylcysteine, (D)-isomerMeSH, HMDB
AcetylinMeSH, HMDB
Azupharma brand OF acetylcysteineMeSH, HMDB
Bisolvon nacMeSH, HMDB
Bouchara brand OF acetylcysteineMeSH, HMDB
Bristol-myers squibb brand OF acetylcysteineMeSH, HMDB
broncho-FipsMeSH, HMDB
BronchoFipsMeSH, HMDB
BroncoclarMeSH, HMDB
FabrolMeSH, HMDB
FrekatussMeSH, HMDB
Guerbet brand OF acetylcysteineMeSH, HMDB
Hydrochloride, acetylcysteineMeSH, HMDB
IlubeMeSH, HMDB
JenacysteinMeSH, HMDB
Krewel brand OF acetylcysteineMeSH, HMDB
LantamedMeSH, HMDB
Lichtenstein brand OF acetylcysteineMeSH, HMDB
m-PectilMeSH, HMDB
Monoammonium salt acetylcysteineMeSH, HMDB
MuciteranMeSH, HMDB
muco SanigenMeSH, HMDB
MucomystMeSH, HMDB
N Acetyl L cysteineMeSH, HMDB
N AcetylcysteineMeSH, HMDB
Pharbita brand OF acetylcysteineMeSH, HMDB
UPSA brand OF acetylcysteineMeSH, HMDB
Ac pharma brand OF acetylcysteineMeSH, HMDB
Ac-pharma brand OF acetylcysteineMeSH, HMDB
AcetylcysteineChEBI
(2R)-2-(Acetylamino)-3-mercaptopropanoic acidbiospider
(2R)-2-Acetamido-3-sulfanyl-propanoic acidbiospider
(2R)-2-acetylamino-3-SulfanylpropanoateGenerator
(2R)-2-acetylamino-3-SulphanylpropanoateGenerator
(2R)-2-acetylamino-3-Sulphanylpropanoic acidGenerator
(R)-2-acetylamino-3-MercaptopropanoateGenerator
2-Acetylamino-3-mercapto-propionatebiospider
2-Acetylamino-3-mercapto-propionic acidbiospider
Aceteinbiospider
L-2-Acetamido-3-mercaptopropanoic acidmanual
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
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)-2ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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.
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSN-Acetyl-L-cysteine, 3 TMS, GC-MS Spectrumsplash10-0i00-2970000000-d817070e3a42f5e63ec5Spectrum
GC-MSN-Acetyl-L-cysteine, non-derivatized, GC-MS Spectrumsplash10-01ox-9000000000-192b8907b32f1e180c72Spectrum
GC-MSN-Acetyl-L-cysteine, non-derivatized, GC-MS Spectrumsplash10-0i00-2970000000-d817070e3a42f5e63ec5Spectrum
Predicted GC-MSN-Acetyl-L-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-13c710ac0e0547e1ec40Spectrum
Predicted GC-MSN-Acetyl-L-cysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0100-9400000000-f5d15a7328f8eeae70feSpectrum
Predicted GC-MSN-Acetyl-L-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-L-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-b0d92bfcc2536077a6fcSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-f305286cee84e6ae992bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-9000000000-b10b4a2a6383336db871Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-056u-9100000000-dee19b6f8563eed2051aSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-193b1f4952acc2d05623Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05i0-9800000000-f7137c548e759655c43bSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9000000000-65dc0cf1be1f7faf55aeSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e55a53ec6cd33256625cSpectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0229-1900000000-3e0a700d54f883459247Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-218c3634602dff3b0ef7Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a6r-9000000000-2f5a099f36fbc10b636bSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9000000000-139c43a5e4b22393c761Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9100000000-85cb2a9affac4a096836Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-cf25c215d3b2da99e302Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0229-3900000000-2b2f710043af50879a7aSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9100000000-a3a7de05cec65f647848Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-9100000000-47a9c1939aac577c2793Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9100000000-be087caed53fbf56c467Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-066r-9000000000-e49809cd4e6d92af0e53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-1900000000-1fd4ac48c9f822eb3500Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-6900000000-d0c51a69ac11096d05c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-218fead85424144539bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-55d7f2c18d3e85caad05Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01zi-6900000000-ceec8ba29592de7e4362Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9200000000-fca1bad01b5fff79588bSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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