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
AcetylcysteineChEBI
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
AcemucHMDB
Acetylcysteine alcon brandHMDB
Acetylcysteine betapharm brandHMDB
Acetylcysteine bouchara brandHMDB
Acetylcysteine farmasan brandHMDB
Acetylcysteine fresenius brandHMDB
Acetylcysteine inpharzam brandHMDB
Acetylcysteine klinge brandHMDB
Acetylcysteine lindopharm brandHMDB
Acetylcysteine pharbita brandHMDB
Acetylcysteine whitehall brandHMDB
Acetylcysteine, monosodium saltHMDB
Acétylcystéine GNRHMDB
Allen and hanburys brand OF acetylcysteineHMDB
Bioiberica brand OF acetylcysteineHMDB
Bristol myers squibb brand OF acetylcysteineHMDB
BromucHMDB
Dey brand OF acetylcysteine sodium saltHMDB
EurespiranHMDB
ExomucHMDB
Fresenius brand OF acetylcysteineHMDB
GNR Pharma brand OF acetylcysteineHMDB
GNR-Pharma brand OF acetylcysteineHMDB
GenacHMDB
Génévrier brand OF acetylcysteineHMDB
Hermes brand OF acetylcysteineHMDB
Heumann brand OF acetylcysteineHMDB
Monosodium salt acetylcysteineHMDB
MucosilHMDB
NAC alHMDB
NAC, bisolvonHMDB
Oberlin brand OF acetylcysteineHMDB
Pfleger brand OF acetylcysteineHMDB
Produpharm lappe brand OF acetylcysteineHMDB
Roberts brand OF acetylcysteineHMDB
Roche nicholas brand OF acetylcysteineHMDB
SiranHMDB
Sodium, acetylcysteineHMDB
Temmler brand OF acetylcysteineHMDB
Teva brand OF acetylcysteineHMDB
Zambon brand OF acetylcysteineHMDB
Zambon, nacHMDB
Acetylcystein atidHMDB
Acetylcystein, mentopinHMDB
Acetylcysteine azupharma brandHMDB
Acetylcysteine centrafarm brandHMDB
Acetylcysteine hermes brandHMDB
Acetylcysteine krewel brandHMDB
Acetylcysteine temmler brandHMDB
Acetylcysteine teva brandHMDB
Acetylcysteine upsa brandHMDB
Acetylcysteine zyma brandHMDB
Acetylcysteine, (DL)-isomerHMDB
Betapharm brand OF acetylcysteineHMDB
Bristol myers squibb brand OF acetylcysteine sodium saltHMDB
Disphar brand OF acetylcysteineHMDB
Farmasan brand OF acetylcysteineHMDB
FluimucilHMDB
JenapharmHMDB
Klinge brand OF acetylcysteineHMDB
Lindopharm brand OF acetylcysteineHMDB
MPectilHMDB
Merck brand OF acetylcysteineHMDB
MucosolHMDB
NAC zambonHMDB
SiccoralHMDB
Trommsdorff brand OF acetylcysteineHMDB
Zyma brand OF acetylcysteineHMDB
Mentopin acetylcysteinHMDB
Acetylcystein alHMDB
Acetylcystein heumannHMDB
Acetylcystein tromHMDB
Acetylcysteine aluid brandHMDB
Acetylcysteine disphar brandHMDB
Acetylcysteine GNR-pharma brandHMDB
Acetylcysteine lichtenstein brandHMDB
Acetylcysteine merck brandHMDB
Acetylcysteine oberlin brandHMDB
Acetylcysteine roberts brandHMDB
Acetylcysteine sodiumHMDB
Acetylcysteine thiemann brandHMDB
Acetylcysteine zincHMDB
Acetylcysteine, monoammonium saltHMDB
AcetystHMDB
Acid, mercapturicHMDB
AirbronHMDB
Alcon brand OF acetylcysteineHMDB
Aluid brand OF acetylcysteineHMDB
AlveolexHMDB
Atid brand OF acetylcysteineHMDB
AzubronchinHMDB
Boehringer ingelheim brand OF acetylcysteineHMDB
Bristol-myers squibb brand OF acetylcysteine sodium saltHMDB
Broncho fipsHMDB
BroncholysinHMDB
Centrafarm brand OF acetylcysteineHMDB
CodotussylHMDB
CystamucilHMDB
Dampo mucopectHMDB
HoestilHMDB
Hustengetränk, optipectHMDB
Inpharzam brand OF acetylcysteineHMDB
Intra brand OF acetylcysteineHMDB
Larylin nacHMDB
LindocetylHMDB
m PectilHMDB
Mucopect, dampoHMDB
MucosolvinHMDB
Optipect hustengetränkHMDB
Sanigen, mucoHMDB
SolmucolHMDB
Thiemann brand OF acetylcysteineHMDB
Whitehall brand OF acetylcysteineHMDB
Zinc, acetylcysteineHMDB
AcebrausHMDB
DurabronchalHMDB
AcetabsHMDB
Acetylcysteine atid brandHMDB
Acetylcysteine bioiberica brandHMDB
Acetylcysteine guerbet brandHMDB
Acetylcysteine génévrier brandHMDB
Acetylcysteine heumann brandHMDB
Acetylcysteine hydrochlorideHMDB
Acetylcysteine intra brandHMDB
Acetylcysteine pfleger brandHMDB
Acetylcysteine trommsdorff brandHMDB
Acetylcysteine zambon brandHMDB
Acetylcysteine ac-pharma brandHMDB
Acetylcysteine, (D)-isomerHMDB
AcetylinHMDB
Azupharma brand OF acetylcysteineHMDB
Bisolvon nacHMDB
Bouchara brand OF acetylcysteineHMDB
Bristol-myers squibb brand OF acetylcysteineHMDB
Broncho-fipsHMDB
BronchoFipsHMDB
BroncoclarHMDB
FabrolHMDB
FrekatussHMDB
Guerbet brand OF acetylcysteineHMDB
Hydrochloride, acetylcysteineHMDB
IlubeHMDB
JenacysteinHMDB
Krewel brand OF acetylcysteineHMDB
LantamedHMDB
Lichtenstein brand OF acetylcysteineHMDB
m-PectilHMDB
Monoammonium salt acetylcysteineHMDB
MuciteranHMDB
Muco sanigenHMDB
MucomystHMDB
N Acetyl L cysteineHMDB
N AcetylcysteineHMDB
Pharbita brand OF acetylcysteineHMDB
UPSA brand OF acetylcysteineHMDB
Ac pharma brand OF acetylcysteineHMDB
Ac-pharma brand OF acetylcysteineHMDB
(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
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)-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
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
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