Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2015-10-09 22:29:42 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-mercaptopropanoic acidbiospider
(2R)-2-Acetamido-3-sulfanyl-propanoic acidbiospider
(2R)-2-acetylamino-3-SulfanylpropanoateGenerator
(2R)-2-Acetylamino-3-sulfanylpropanoic acidbiospider
(2R)-2-acetylamino-3-SulphanylpropanoateGenerator
(2R)-2-acetylamino-3-Sulphanylpropanoic acidGenerator
(R)-2-acetylamino-3-MercaptopropanoateGenerator
(R)-2-Acetylamino-3-mercaptopropanoic acidbiospider
(R)-MercaptateGenerator
(R)-Mercaptic acidGenerator
(R)-Mercapturic acidChEBI
2-Acetylamino-3-mercapto-propionatebiospider
2-Acetylamino-3-mercapto-propionic acidbiospider
Acetadotebiospider
Aceteinbiospider
AcetilcisteinaChEBI
Acetylcysteinemanual
AcetylcysteinumChEBI
Airbrondb_source
Fabroldb_source
Fluimicil infantilHMDB
FluimucetinHMDB
FlumucetinHMDB
FluprowitHMDB
L-2-Acetamido-3-mercaptopropanoic acidmanual
L-a-acetamido-b-MercaptopropionateGenerator
L-a-acetamido-b-Mercaptopropionic acidGenerator
L-Acetylcysteinemanual
L-alpha-acetamido-beta-MercaptopropionateGenerator
L-alpha-Acetamido-beta-mercaptopropionic acidbiospider
L-α-acetamido-β-mercaptopropionateGenerator
L-α-acetamido-β-mercaptopropionic acidGenerator
Lysomucilbiospider
MercaptateGenerator
Mercaptic acidGenerator
Mercapturic acidChEBI
Mucomystdb_source
N-Acety-L-cysteineHMDB
N-Acetyl cysteinebiospider
N-Acetyl-3-mercaptoalaninebiospider
N-Acetyl-L-(+)-cysteinebiospider
N-Acetyl-L-cysteinebiospider
N-Acetylcysteinebiospider
N-Acetylcysteine; L-formdb_source
NACbiospider
NSC 111180db_source
Parvolexdb_source
Respairedb_source
Sodium 2-acetamido-3-mercaptopropionateHMDB
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 KeyInChIKey=PWKSKIMOESPYIA-BYPYZUCNSA-N
Isomeric SMILESCC(=O)N[C@@H](CS)C(O)=O
Average Molecular Weight163
Monoisotopic Molecular Weight163
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