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
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
Physico-Chemical Properties - Experimental
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-b0d92bfcc2536077a6fc2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-f305286cee84e6ae992b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-9000000000-b10b4a2a6383336db8712012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-056u-9100000000-dee19b6f8563eed2051a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-193b1f4952acc2d056232021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05i0-9800000000-f7137c548e759655c43b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9000000000-65dc0cf1be1f7faf55ae2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e55a53ec6cd33256625c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0229-1900000000-3e0a700d54f8834592472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-218c3634602dff3b0ef72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a6r-9000000000-2f5a099f36fbc10b636b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9000000000-139c43a5e4b22393c7612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9100000000-85cb2a9affac4a0968362021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-cf25c215d3b2da99e3022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0229-3900000000-2b2f710043af50879a7a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9100000000-a3a7de05cec65f6478482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-9100000000-47a9c1939aac577c27932021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9100000000-be087caed53fbf56c4672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-066r-9000000000-e49809cd4e6d92af0e532021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-1900000000-1fd4ac48c9f822eb35002017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-6900000000-d0c51a69ac11096d05c32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-218fead85424144539bd2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-55d7f2c18d3e85caad052017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01zi-6900000000-ceec8ba29592de7e43622017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9200000000-fca1bad01b5fff79588b2017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference