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Record Information
Version1.0
Creation Date2016-09-30 22:48:39 UTC
Update Date2020-06-04 20:22:20 UTC
BMDB IDBMDB0001890
Secondary Accession Numbers
  • BMDB01890
Metabolite Identification
Common NameAcetylcysteine
DescriptionAcetylcysteine, also known as NAC or (R)-mercaptate, 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. Acetylcysteine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. In cattle, acetylcysteine is involved in the metabolic pathway called the cysteine metabolism pathway.
Structure
Thumb
Synonyms
Chemical FormulaC5H9NO3S
Average Molecular Weight163.195
Monoisotopic Molecular Weight163.030313849
IUPAC Name(2R)-2-acetamido-3-sulfanylpropanoic acid
Traditional Nameacetylcysteine
CAS Registry Number616-91-1
SMILES
CC(=O)N[C@@H](CS)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point109.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-056u-9100000000-dee19b6f8563eed2051aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-193b1f4952acc2d05623View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05i0-9800000000-f7137c548e759655c43bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9000000000-65dc0cf1be1f7faf55aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e55a53ec6cd33256625cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0229-1900000000-3e0a700d54f883459247View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-218c3634602dff3b0ef7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a6r-9000000000-2f5a099f36fbc10b636bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9000000000-139c43a5e4b22393c761View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9100000000-85cb2a9affac4a096836View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-cf25c215d3b2da99e302View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0229-3900000000-2b2f710043af50879a7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9100000000-a3a7de05cec65f647848View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-9100000000-47a9c1939aac577c2793View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9100000000-be087caed53fbf56c467View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-066r-9000000000-e49809cd4e6d92af0e53View 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 Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Myelin sheath
Biospecimen Locations
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Milk
  • Neuron
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0001890
DrugBank IDDB06151
Phenol Explorer Compound IDNot Available
FooDB IDFDB002281
KNApSAcK IDNot Available
Chemspider ID11540
KEGG Compound IDC06809
BioCyc IDCPD-9175
BiGG IDNot Available
Wikipedia LinkAcetylcysteine
METLIN ID784
PubChem Compound12035
PDB IDNot Available
ChEBI ID28939
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]