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Showing NP-Card for Acetylcysteine (NP0001180)

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Record Information
Version2.0
Created at2006-02-28 17:19:06 UTC
Updated at2024-09-17 15:44:21 UTC
NP-MRD IDNP0001180
Natural Product DOIhttps://doi.org/10.57994/2722
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetylcysteine
DescriptionAcetylcysteine is the N-acetyl derivative of the amino acid L-cysteine, and is a precursor in the formation of the antioxidant glutathione in the body. The thiol (sulfhydryl) group confers antioxidant effects and is able to reduce free radicals. Wikipedia. It is used as a mucolytic agent to reduce the viscosity of mucous secretions. It has also been shown to have antiviral effects in patients with HIV due to inhibition of viral stimulation by reactive oxygen intermediates. Acetylcysteine is a pharmacological agent used in the management of paracetamol overdose. For these indications, acetylcysteine is available under the trade names Mucomyst (Bristol-Myers Squibb) and Parvolex.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001180 (Acetylcysteine)


  Mrv1652305271900012D          

 10  9  0  0  1  0            999 V2000
    2.8073   -0.9817    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    0.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073    1.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2362    0.6682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5217   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6651    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  2  0  0  0  0
  6  5  1  1  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for NP0001180 (Acetylcysteine)

HMDB0001890
     RDKit          3D
Acetylcysteine
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.1092   -0.6575    0.5971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896   -0.1277   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0246    0.5165   -1.1095 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -0.3102    0.5011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    0.2246   -0.1524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5269   -0.8883   -0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9703   -0.1767   -1.3998 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.1002    0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943    1.3476    1.9469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4888    1.7170    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -1.6030    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.0691    1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8255   -0.9633   -0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621   -0.8472    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830    0.7570   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036   -1.4410    0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384   -1.6046   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784    0.1645   -2.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818    2.7232    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  6
  6 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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3D SDF for NP0001180 (Acetylcysteine)


  Mrv1652305271900012D          

 10  9  0  0  1  0            999 V2000
    2.8073   -0.9817    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    0.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073    1.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2362    0.6682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5217   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6651    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  2  0  0  0  0
  6  5  1  1  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001180

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
PWKSKIMOESPYIA-BYPYZUCNSA-N

> <FORMULA>
C5H9NO3S

> <MOLECULAR_WEIGHT>
163.195

> <EXACT_MASS>
163.030313849

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.339275209613305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-acetamido-3-sulfanylpropanoic acid

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-0.7113127423333335

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.049469514327951

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8175772994337542

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9961464741729809

> <JCHEM_POLAR_SURFACE_AREA>
66.39999999999999

> <JCHEM_REFRACTIVITY>
37.6674

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylcysteine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001180 (Acetylcysteine)

HMDB0001890
     RDKit          3D
Acetylcysteine
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.1092   -0.6575    0.5971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896   -0.1277   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0246    0.5165   -1.1095 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -0.3102    0.5011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    0.2246   -0.1524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5269   -0.8883   -0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9703   -0.1767   -1.3998 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.1002    0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943    1.3476    1.9469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4888    1.7170    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -1.6030    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.0691    1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8255   -0.9633   -0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621   -0.8472    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830    0.7570   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036   -1.4410    0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384   -1.6046   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784    0.1645   -2.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818    2.7232    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  6
  6 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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PDB for NP0001180 (Acetylcysteine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0       5.240  -1.833   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.907   0.477   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.240   2.787   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.241  -1.063   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.908   1.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.574   0.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -1.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.240   1.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.241   0.477   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.575   1.247   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    9                                                            
CONECT    5    6    9                                                       
CONECT    6    5    7    8                                                  
CONECT    7    1    6                                                       
CONECT    8    2    3    6                                                  
CONECT    9    4    5   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0001180 (Acetylcysteine)

COMPND    HMDB0001890
HETATM    1  C1  UNL     1       3.109  -0.658   0.597  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.890  -0.128  -0.037  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.025   0.517  -1.109  1.00  0.00           O  
HETATM    4  N1  UNL     1       0.590  -0.310   0.501  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.568   0.225  -0.152  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.527  -0.888  -0.583  1.00  0.00           C  
HETATM    7  S1  UNL     1      -2.970  -0.177  -1.400  1.00  0.00           S  
HETATM    8  C5  UNL     1      -1.315   1.100   0.767  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.994   1.348   1.947  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.489   1.717   0.295  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.842  -1.603   1.119  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.606   0.069   1.273  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.826  -0.963  -0.219  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.462  -0.847   1.398  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.283   0.757  -1.069  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.904  -1.441   0.314  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.038  -1.605  -1.268  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.678   0.165  -2.740  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.582   2.723   0.366  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14
CONECT    5    6    8   15
CONECT    6    7   16   17
CONECT    7   18
CONECT    8    9    9   10
CONECT   10   19
END
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SMILES for NP0001180 (Acetylcysteine)

CC(=O)N[C@@H](CS)C(O)=O
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INCHI for NP0001180 (Acetylcysteine)

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
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View in JSmolView NMR Assignments
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
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
AcetylcysteineChEBI
Chemical FormulaC5H9NO3S
Average Mass163.1950 Da
Monoisotopic Mass163.03031 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-03View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-03View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-03View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, D2O, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Actaea simplexLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point109.5 °CNot Available
Boiling Point407.00 to 408.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility242900 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.696 (est)The Good Scents Company Information System
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
HMDB IDHMDB0001890
DrugBank IDDB06151
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1265501
References
General References
  1. Faucet-Marquis V, Pont F, Stormer FC, Rizk T, Castegnaro M, Pfohl-Leszkowicz A: Evidence of a new dechlorinated ochratoxin A derivative formed in opossum kidney cell cultures after pretreatment by modulators of glutathione pathways: correlation with DNA-adduct formation. Mol Nutr Food Res. 2006 May;50(6):530-42. [PubMed:16671059 ]
  2. Wilkes JM, Clark LE, Herrera JL: Acetaminophen overdose in pregnancy. South Med J. 2005 Nov;98(11):1118-22. [PubMed:16351032 ]
  3. Weigand MA, Plachky J, Thies JC, Spies-Martin D, Otto G, Martin E, Bardenheuer HJ: N-acetylcysteine attenuates the increase in alpha-glutathione S-transferase and circulating ICAM-1 and VCAM-1 after reperfusion in humans undergoing liver transplantation. Transplantation. 2001 Aug 27;72(4):694-8. [PubMed:11544433 ]
  4. Soheili Majd E, Goldberg M, Stanislawski L: In vitro effects of ascorbate and Trolox on the biocompatibility of dental restorative materials. Biomaterials. 2003 Jan;24(1):3-9. [PubMed:12417172 ]
  5. Cereser C, Boget S, Parvaz P, Revol A: Thiram-induced cytotoxicity is accompanied by a rapid and drastic oxidation of reduced glutathione with consecutive lipid peroxidation and cell death. Toxicology. 2001 Jun 21;163(2-3):153-62. [PubMed:11516525 ]
  6. Hein OV, Ohring R, Schilling A, Oellerich M, Armstrong VW, Kox WJ, Spies C: N-acetylcysteine decreases lactate signal intensities in liver tissue and improves liver function in septic shock patients, as shown by magnetic resonance spectroscopy: extended case report. Crit Care. 2004 Apr;8(2):R66-71. Epub 2004 Jan 22. [PubMed:15025780 ]
  7. Kramers C, Jansman FG, Droogleever Fortuyn H: [A patient who refused treatment after self-poisoning with paracetamol]. Ned Tijdschr Geneeskd. 2006 Jul 22;150(29):1601-4. [PubMed:16901061 ]
  8. Lucena MI, Lopez-Torres E, Verge C, Andrade RJ, Puche MJ, Seoane J, de la Cuesta FS: The administration of N-acetylcysteine causes a decrease in prothrombin time in patients with paracetamol overdose but without evidence of liver impairment. Eur J Gastroenterol Hepatol. 2005 Jan;17(1):59-63. [PubMed:15647642 ]
  9. Langman M, Boyle P: Chemoprevention of colorectal cancer. Gut. 1998 Oct;43(4):578-85. [PubMed:9824590 ]
  10. Alscher DM, Braun N, Biegger D, Stuelten C, Gawronski K, Murdter TE, Kuhlmann U, Fritz P: Induction of metallothionein in proximal tubular cells by zinc and its potential as an endogenous antioxidant. Kidney Blood Press Res. 2005;28(3):127-33. Epub 2005 Apr 5. [PubMed:15812196 ]
  11. Hook GE, Gilmore LB, Talley FA: Dissolution and reassembly of tubular myelin-like multilamellated structures from the lungs of patients with pulmonary alveolar proteinosis. Lab Invest. 1986 Aug;55(2):194-208. [PubMed:3755483 ]
  12. Dawson AH, Henry DA, McEwen J: Adverse reactions to N-acetylcysteine during treatment for paracetamol poisoning. Med J Aust. 1989 Mar 20;150(6):329-31. [PubMed:2716644 ]
  13. Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. [PubMed:9624310 ]
  14. Jones AL: Mechanism of action and value of N-acetylcysteine in the treatment of early and late acetaminophen poisoning: a critical review. J Toxicol Clin Toxicol. 1998;36(4):277-85. [PubMed:9711192 ]
  15. Fulghesu AM, Ciampelli M, Muzj G, Belosi C, Selvaggi L, Ayala GF, Lanzone A: N-acetyl-cysteine treatment improves insulin sensitivity in women with polycystic ovary syndrome. Fertil Steril. 2002 Jun;77(6):1128-35. [PubMed:12057717 ]