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
ValueSource
(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
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
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 ]