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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:25:00 UTC

Update Date

2021-09-26 23:11:35 UTC

HMDB ID

HMDB0256120

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Paracetamol cysteine

Description

Paracetamol cysteine belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Based on a literature review a significant number of articles have been published on Paracetamol cysteine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Paracetamol cysteine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Paracetamol cysteine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0256120
     RDKit          3D
Paracetamol cysteine
 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.2963    0.3557    0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562    0.7359    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6023    1.9498    0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765   -0.2331   -0.0470 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926   -0.0549   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8388    1.1546   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562    1.2764   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184    0.1824   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877    0.2251   -0.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.0906    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.0872    1.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    0.1464    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785    0.3531   -1.3348 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669   -1.1252    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5357   -0.8951    0.1143 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216   -1.0315   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814   -1.1649   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3912   -0.5788    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8892    1.1185    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7245    0.2086   -0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455   -1.2298   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009    2.0653    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    2.2490   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306    0.9707    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642    0.9928   -1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4491   -0.5109   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4111   -2.0052   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -1.2797    1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167    0.1808   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2800   -1.9254   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -2.1343   -0.5407 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

  Mrv1652309112118252D          

 17 17  0  0  0  0            999 V2000
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256120

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC1=CC=C(OC(=O)C(N)CS)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O3S/c1-7(14)13-8-2-4-9(5-3-8)16-11(15)10(12)6-17/h2-5,10,17H,6,12H2,1H3,(H,13,14)

> <INCHI_KEY>
VKVHWTMZJQWYBR-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O3S

> <MOLECULAR_WEIGHT>
254.3

> <EXACT_MASS>
254.072513493

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.498251614450936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-acetamidophenyl 2-amino-3-sulfanylpropanoate

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
0.5114035266666664

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.667633710956085

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.95831626978614

> <JCHEM_PKA_STRONGEST_BASIC>
6.9035836587702155

> <JCHEM_POLAR_SURFACE_AREA>
81.42

> <JCHEM_REFRACTIVITY>
67.6333

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-acetamidophenyl 2-amino-3-sulfanylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256120
     RDKit          3D
Paracetamol cysteine
 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.2963    0.3557    0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562    0.7359    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6023    1.9498    0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765   -0.2331   -0.0470 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926   -0.0549   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8388    1.1546   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562    1.2764   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184    0.1824   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877    0.2251   -0.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.0906    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.0872    1.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    0.1464    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785    0.3531   -1.3348 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669   -1.1252    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5357   -0.8951    0.1143 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216   -1.0315   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814   -1.1649   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3912   -0.5788    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8892    1.1185    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7245    0.2086   -0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455   -1.2298   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009    2.0653    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    2.2490   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306    0.9707    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642    0.9928   -1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4491   -0.5109   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4111   -2.0052   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -1.2797    1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167    0.1808   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2800   -1.9254   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -2.1343   -0.5407 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -4.001   2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       6.668   5.390   0.000  0.00  0.00           S+0
HETATM   17  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0256120
HETATM    1  C1  UNL     1      -6.296   0.356   0.350  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.856   0.736   0.219  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.602   1.950   0.360  1.00  0.00           O  
HETATM    4  N1  UNL     1      -3.876  -0.233  -0.047  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.493  -0.055  -0.200  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.839   1.155  -0.110  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.456   1.276  -0.271  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.318   0.182  -0.529  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.688   0.225  -0.700  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.607   0.091   0.301  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.211  -0.087   1.481  1.00  0.00           O  
HETATM   12  C8  UNL     1       4.059   0.146   0.048  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.378   0.353  -1.335  1.00  0.00           N  
HETATM   14  C9  UNL     1       4.767  -1.125   0.493  1.00  0.00           C  
HETATM   15  S1  UNL     1       6.536  -0.895   0.114  1.00  0.00           S  
HETATM   16  C10 UNL     1      -0.322  -1.032  -0.622  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.681  -1.165  -0.465  1.00  0.00           C  
HETATM   18  H1  UNL     1      -6.391  -0.579   0.972  1.00  0.00           H  
HETATM   19  H2  UNL     1      -6.889   1.119   0.867  1.00  0.00           H  
HETATM   20  H3  UNL     1      -6.725   0.209  -0.653  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.245  -1.230  -0.142  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.401   2.065   0.094  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.004   2.249  -0.190  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.531   0.971   0.651  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.664   0.993  -1.746  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.449  -0.511  -1.897  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.411  -2.005  -0.084  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.632  -1.280   1.595  1.00  0.00           H  
HETATM   29  H12 UNL     1       6.717   0.181  -0.803  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.280  -1.925  -0.828  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.178  -2.134  -0.541  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5   21
CONECT    5    6    6   17
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   16
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   14   24
CONECT   13   25   26
CONECT   14   15   27   28
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   31
END

HMDB0256120
     RDKit          3D
Paracetamol cysteine
 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.2963    0.3557    0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562    0.7359    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6023    1.9498    0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765   -0.2331   -0.0470 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926   -0.0549   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8388    1.1546   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562    1.2764   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184    0.1824   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877    0.2251   -0.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.0906    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.0872    1.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    0.1464    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785    0.3531   -1.3348 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669   -1.1252    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5357   -0.8951    0.1143 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216   -1.0315   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814   -1.1649   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3912   -0.5788    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8892    1.1185    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7245    0.2086   -0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455   -1.2298   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009    2.0653    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    2.2490   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306    0.9707    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642    0.9928   -1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4491   -0.5109   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4111   -2.0052   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -1.2797    1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167    0.1808   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2800   -1.9254   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -2.1343   -0.5407 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-{4-[(2-amino-3-sulfanylpropanoyl)oxy]phenyl}ethanimidate	HMDB
N-{4-[(2-amino-3-sulphanylpropanoyl)oxy]phenyl}ethanimidate	HMDB
N-{4-[(2-amino-3-sulphanylpropanoyl)oxy]phenyl}ethanimidic acid	HMDB

Chemical Formula

C₁₁H₁₄N₂O₃S

Average Molecular Weight

254.3

Monoisotopic Molecular Weight

254.072513493

IUPAC Name

4-acetamidophenyl 2-amino-3-sulfanylpropanoate

Traditional Name

4-acetamidophenyl 2-amino-3-sulfanylpropanoate

CAS Registry Number

Not Available

SMILES

CC(=O)NC1=CC=C(OC(=O)C(N)CS)C=C1

InChI Identifier

InChI=1S/C11H14N2O3S/c1-7(14)13-8-2-4-9(5-3-8)16-11(15)10(12)6-17/h2-5,10,17H,6,12H2,1H3,(H,13,14)

InChI Key

VKVHWTMZJQWYBR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Cysteine or derivatives
Acetanilide
Phenol ester
N-acetylarylamine
Anilide
Phenoxy compound
N-arylamide
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Alkylthiol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Primary amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.37	ALOGPS
logP	0.51	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	6.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.63 m³·mol⁻¹	ChemAxon
Polarizability	26.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	155.815	30932474
DeepCCS	[M-H]-	153.419	30932474
DeepCCS	[M-2H]-	186.402	30932474
DeepCCS	[M+Na]+	161.851	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	159.5	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	157.2	32859911
AllCCS	[M+Na-2H]-	157.7	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Paracetamol cysteine	CC(=O)NC1=CC=C(OC(=O)C(N)CS)C=C1	3508.0	Standard polar	33892256
Paracetamol cysteine	CC(=O)NC1=CC=C(OC(=O)C(N)CS)C=C1	2300.1	Standard non polar	33892256
Paracetamol cysteine	CC(=O)NC1=CC=C(OC(=O)C(N)CS)C=C1	2542.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Paracetamol cysteine,1TMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(N)CS[Si](C)(C)C)C=C1	2623.1	Semi standard non polar	33892256
Paracetamol cysteine,1TMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(N)CS[Si](C)(C)C)C=C1	2464.2	Standard non polar	33892256
Paracetamol cysteine,1TMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(N)CS[Si](C)(C)C)C=C1	3846.1	Standard polar	33892256
Paracetamol cysteine,1TMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS)N[Si](C)(C)C)C=C1	2581.9	Semi standard non polar	33892256
Paracetamol cysteine,1TMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS)N[Si](C)(C)C)C=C1	2250.9	Standard non polar	33892256
Paracetamol cysteine,1TMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS)N[Si](C)(C)C)C=C1	3312.8	Standard polar	33892256
Paracetamol cysteine,1TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(N)CS)C=C1)[Si](C)(C)C	2272.2	Semi standard non polar	33892256
Paracetamol cysteine,1TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(N)CS)C=C1)[Si](C)(C)C	2185.3	Standard non polar	33892256
Paracetamol cysteine,1TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(N)CS)C=C1)[Si](C)(C)C	3643.5	Standard polar	33892256
Paracetamol cysteine,2TMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C)N[Si](C)(C)C)C=C1	2696.8	Semi standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C)N[Si](C)(C)C)C=C1	2512.6	Standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C)N[Si](C)(C)C)C=C1	3363.2	Standard polar	33892256
Paracetamol cysteine,2TMS,isomer #2	CC(=O)N(C1=CC=C(OC(=O)C(N)CS[Si](C)(C)C)C=C1)[Si](C)(C)C	2437.2	Semi standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #2	CC(=O)N(C1=CC=C(OC(=O)C(N)CS[Si](C)(C)C)C=C1)[Si](C)(C)C	2461.8	Standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #2	CC(=O)N(C1=CC=C(OC(=O)C(N)CS[Si](C)(C)C)C=C1)[Si](C)(C)C	3339.0	Standard polar	33892256
Paracetamol cysteine,2TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N[Si](C)(C)C)C=C1)[Si](C)(C)C	2364.8	Semi standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N[Si](C)(C)C)C=C1)[Si](C)(C)C	2291.5	Standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N[Si](C)(C)C)C=C1)[Si](C)(C)C	2957.2	Standard polar	33892256
Paracetamol cysteine,2TMS,isomer #4	CC(=O)NC1=CC=C(OC(=O)C(CS)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2721.6	Semi standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #4	CC(=O)NC1=CC=C(OC(=O)C(CS)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2472.4	Standard non polar	33892256
Paracetamol cysteine,2TMS,isomer #4	CC(=O)NC1=CC=C(OC(=O)C(CS)N([Si](C)(C)C)[Si](C)(C)C)C=C1	3090.8	Standard polar	33892256
Paracetamol cysteine,3TMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C)N[Si](C)(C)C)C=C1)[Si](C)(C)C	2484.6	Semi standard non polar	33892256
Paracetamol cysteine,3TMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C)N[Si](C)(C)C)C=C1)[Si](C)(C)C	2481.3	Standard non polar	33892256
Paracetamol cysteine,3TMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C)N[Si](C)(C)C)C=C1)[Si](C)(C)C	2909.1	Standard polar	33892256
Paracetamol cysteine,3TMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2817.1	Semi standard non polar	33892256
Paracetamol cysteine,3TMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2627.7	Standard non polar	33892256
Paracetamol cysteine,3TMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	3146.7	Standard polar	33892256
Paracetamol cysteine,3TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2517.3	Semi standard non polar	33892256
Paracetamol cysteine,3TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2502.5	Standard non polar	33892256
Paracetamol cysteine,3TMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2835.4	Standard polar	33892256
Paracetamol cysteine,4TMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2638.2	Semi standard non polar	33892256
Paracetamol cysteine,4TMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2593.2	Standard non polar	33892256
Paracetamol cysteine,4TMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2768.8	Standard polar	33892256
Paracetamol cysteine,1TBDMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(N)CS[Si](C)(C)C(C)(C)C)C=C1	2871.4	Semi standard non polar	33892256
Paracetamol cysteine,1TBDMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(N)CS[Si](C)(C)C(C)(C)C)C=C1	2700.4	Standard non polar	33892256
Paracetamol cysteine,1TBDMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(N)CS[Si](C)(C)C(C)(C)C)C=C1	3818.4	Standard polar	33892256
Paracetamol cysteine,1TBDMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS)N[Si](C)(C)C(C)(C)C)C=C1	2819.8	Semi standard non polar	33892256
Paracetamol cysteine,1TBDMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS)N[Si](C)(C)C(C)(C)C)C=C1	2495.4	Standard non polar	33892256
Paracetamol cysteine,1TBDMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS)N[Si](C)(C)C(C)(C)C)C=C1	3337.6	Standard polar	33892256
Paracetamol cysteine,1TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(N)CS)C=C1)[Si](C)(C)C(C)(C)C	2506.1	Semi standard non polar	33892256
Paracetamol cysteine,1TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(N)CS)C=C1)[Si](C)(C)C(C)(C)C	2411.1	Standard non polar	33892256
Paracetamol cysteine,1TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(N)CS)C=C1)[Si](C)(C)C(C)(C)C	3647.6	Standard polar	33892256
Paracetamol cysteine,2TBDMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C1	3210.3	Semi standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C1	2932.6	Standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #1	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C1	3373.2	Standard polar	33892256
Paracetamol cysteine,2TBDMS,isomer #2	CC(=O)N(C1=CC=C(OC(=O)C(N)CS[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2908.0	Semi standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #2	CC(=O)N(C1=CC=C(OC(=O)C(N)CS[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2859.5	Standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #2	CC(=O)N(C1=CC=C(OC(=O)C(N)CS[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3366.0	Standard polar	33892256
Paracetamol cysteine,2TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2778.1	Semi standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2722.3	Standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3100.5	Standard polar	33892256
Paracetamol cysteine,2TBDMS,isomer #4	CC(=O)NC1=CC=C(OC(=O)C(CS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3187.7	Semi standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #4	CC(=O)NC1=CC=C(OC(=O)C(CS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2864.5	Standard non polar	33892256
Paracetamol cysteine,2TBDMS,isomer #4	CC(=O)NC1=CC=C(OC(=O)C(CS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3152.7	Standard polar	33892256
Paracetamol cysteine,3TBDMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3109.9	Semi standard non polar	33892256
Paracetamol cysteine,3TBDMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3037.7	Standard non polar	33892256
Paracetamol cysteine,3TBDMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3162.8	Standard polar	33892256
Paracetamol cysteine,3TBDMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3562.0	Semi standard non polar	33892256
Paracetamol cysteine,3TBDMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3199.0	Standard non polar	33892256
Paracetamol cysteine,3TBDMS,isomer #2	CC(=O)NC1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3295.9	Standard polar	33892256
Paracetamol cysteine,3TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3178.2	Semi standard non polar	33892256
Paracetamol cysteine,3TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3062.9	Standard non polar	33892256
Paracetamol cysteine,3TBDMS,isomer #3	CC(=O)N(C1=CC=C(OC(=O)C(CS)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3053.1	Standard polar	33892256
Paracetamol cysteine,4TBDMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3555.9	Semi standard non polar	33892256
Paracetamol cysteine,4TBDMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3283.3	Standard non polar	33892256
Paracetamol cysteine,4TBDMS,isomer #1	CC(=O)N(C1=CC=C(OC(=O)C(CS[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3097.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Paracetamol cysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9400000000-4f7fc86e5d5b65003270	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paracetamol cysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14481642

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19901183

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Paracetamol cysteine (HMDB0256120)

MOL for HMDB0256120 (Paracetamol cysteine)

3D MOL for HMDB0256120 (Paracetamol cysteine)

3D SDF for HMDB0256120 (Paracetamol cysteine)

3D-SDF for HMDB0256120 (Paracetamol cysteine)

PDB for HMDB0256120 (Paracetamol cysteine)

3D PDB for HMDB0256120 (Paracetamol cysteine)

SMILES for HMDB0256120 (Paracetamol cysteine)

INCHI for HMDB0256120 (Paracetamol cysteine)

Structure for HMDB0256120 (Paracetamol cysteine)

3D Structure for HMDB0256120 (Paracetamol cysteine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra