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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-27 04:23:36 UTC

Update Date

2022-09-22 18:35:13 UTC

HMDB ID

HMDB0242140

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acetaminophen mercapturate

Description

Acetaminophen mercapturate 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. Acetaminophen mercapturate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Acetaminophen mercapturate.

Structure

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

HMDB0242140
     RDKit          3D
Acetaminophen mercapturate
 37 37  0  0  0  0  0  0  0  0999 V2000
    6.4001    1.3766    0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2279    0.7003    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    0.8907   -1.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221   -0.0179    0.8445 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111   -0.6554    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3452   -1.9815   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -2.5878   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -1.8464   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -2.4929   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -0.5457   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.4245   -0.7347 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410    0.1873    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -0.1947    0.2805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5361    0.8652   -0.5238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7712    1.0787   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0542    2.2724   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8465    0.3619   -0.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7096   -0.2174    1.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778    0.7704    1.8762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -1.2927    2.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420    0.0378    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3296    0.9594    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150    1.3098    1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613    2.4404    0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.6542   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571   -2.5509   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -3.6063   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -2.0108   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -0.6689    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.0648    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0487   -1.1446   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757    2.8924   -1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649    2.9473   -1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3957    1.9457   -2.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2447   -0.4703   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621   -1.9645    2.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743    1.0692    0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
 13 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  2  0
 21  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv1652308272106332D          

 22 22  0  0  1  0            999 V2000
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  4  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 14  9  1  4  0  0  0
 15  8  2  0  0  0  0
 10 15  1  1  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
 21  6  1  0  0  0  0
 21 12  1  0  0  0  0
 10 22  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0242140

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](CSC1=C(O)C=CC(=C1)N=C(C)O)(N=C(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O5S/c1-7(16)14-9-3-4-11(18)12(5-9)21-6-10(13(19)20)15-8(2)17/h3-5,10,18H,6H2,1-2H3,(H,14,16)(H,15,17)(H,19,20)/t10-/m0/s1

> <INCHI_KEY>
DVPRQNKJGQEICH-JTQLQIEISA-N

> <FORMULA>
C13H16N2O5S

> <MOLECULAR_WEIGHT>
312.34

> <EXACT_MASS>
312.077992797

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.977579230237914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-3-({2-hydroxy-5-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)-2-[(1-hydroxyethylidene)amino]propanoic acid

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
1.3898606440566215

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.0556335660151355

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1366067513873985

> <JCHEM_PKA_STRONGEST_BASIC>
1.441878893018413

> <JCHEM_POLAR_SURFACE_AREA>
122.71000000000002

> <JCHEM_REFRACTIVITY>
80.36430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-({2-hydroxy-5-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)-2-[(1-hydroxyethylidene)amino]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242140
     RDKit          3D
Acetaminophen mercapturate
 37 37  0  0  0  0  0  0  0  0999 V2000
    6.4001    1.3766    0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2279    0.7003    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    0.8907   -1.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221   -0.0179    0.8445 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111   -0.6554    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3452   -1.9815   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -2.5878   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -1.8464   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -2.4929   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -0.5457   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.4245   -0.7347 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410    0.1873    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -0.1947    0.2805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5361    0.8652   -0.5238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7712    1.0787   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0542    2.2724   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8465    0.3619   -0.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7096   -0.2174    1.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778    0.7704    1.8762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -1.2927    2.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420    0.0378    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3296    0.9594    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150    1.3098    1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613    2.4404    0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.6542   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571   -2.5509   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -3.6063   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -2.0108   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -0.6689    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.0648    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0487   -1.1446   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757    2.8924   -1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649    2.9473   -1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3957    1.9457   -2.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2447   -0.4703   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621   -1.9645    2.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743    1.0692    0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
 13 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  2  0
 21  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 27-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-AUG-21         0                                  
HETATM    1  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      10.669   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0       8.002   4.620   0.000  0.00  0.00           S+0
HETATM   22  H   UNK     0       6.668   5.390   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    9   12                                                       
CONECT    6   10   21                                                       
CONECT    7    1   14   16                                                  
CONECT    8    2   15   17                                                  
CONECT    9    3    5   14                                                  
CONECT   10    6   13   15   22                                             
CONECT   11    4   12   18                                                  
CONECT   12    5   11   21                                                  
CONECT   13   10   19   20                                                  
CONECT   14    7    9                                                       
CONECT   15    8   10                                                       
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21    6   12                                                       
CONECT   22   10                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0242140
HETATM    1  C1  UNL     1       6.400   1.377   0.790  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.228   0.700   0.147  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.068   0.891  -1.212  1.00  0.00           O  
HETATM    4  N1  UNL     1       4.422  -0.018   0.845  1.00  0.00           N  
HETATM    5  C3  UNL     1       3.311  -0.655   0.237  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.345  -1.982  -0.177  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.263  -2.588  -0.754  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.086  -1.846  -0.933  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.009  -2.493  -1.521  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.011  -0.546  -0.543  1.00  0.00           C  
HETATM   11  S1  UNL     1      -0.471   0.424  -0.735  1.00  0.00           S  
HETATM   12  C8  UNL     1      -1.541   0.187   0.671  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.971  -0.195   0.281  1.00  0.00           C  
HETATM   14  N2  UNL     1      -3.536   0.865  -0.524  1.00  0.00           N  
HETATM   15  C10 UNL     1      -4.771   1.079  -0.763  1.00  0.00           C  
HETATM   16  C11 UNL     1      -5.054   2.272  -1.639  1.00  0.00           C  
HETATM   17  O3  UNL     1      -5.847   0.362  -0.319  1.00  0.00           O  
HETATM   18  C12 UNL     1      -3.710  -0.217   1.577  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.478   0.770   1.876  1.00  0.00           O  
HETATM   20  O5  UNL     1      -3.570  -1.293   2.447  1.00  0.00           O  
HETATM   21  C13 UNL     1       2.142   0.038   0.044  1.00  0.00           C  
HETATM   22  H1  UNL     1       7.330   0.959   0.414  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.315   1.310   1.892  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.361   2.440   0.525  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.857   0.654  -1.795  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.257  -2.551  -0.038  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.258  -3.606  -1.078  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.873  -2.011  -1.667  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.206  -0.669   1.317  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.602   1.065   1.330  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.049  -1.145  -0.231  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.876   2.892  -1.199  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.165   2.947  -1.714  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.396   1.946  -2.638  1.00  0.00           H  
HETATM   35  H14 UNL     1      -6.245  -0.470  -0.743  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.362  -1.964   2.487  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.074   1.069   0.354  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    4
CONECT    3   25
CONECT    4    5
CONECT    5    6    6   21
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   10
CONECT    9   28
CONECT   10   11   21   21
CONECT   11   12
CONECT   12   13   29   30
CONECT   13   14   18   31
CONECT   14   15   15
CONECT   15   16   17
CONECT   16   32   33   34
CONECT   17   35
CONECT   18   19   19   20
CONECT   20   36
CONECT   21   37
END

HMDB0242140
     RDKit          3D
Acetaminophen mercapturate
 37 37  0  0  0  0  0  0  0  0999 V2000
    6.4001    1.3766    0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2279    0.7003    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    0.8907   -1.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221   -0.0179    0.8445 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111   -0.6554    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3452   -1.9815   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -2.5878   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -1.8464   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -2.4929   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -0.5457   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.4245   -0.7347 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410    0.1873    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -0.1947    0.2805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5361    0.8652   -0.5238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7712    1.0787   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0542    2.2724   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8465    0.3619   -0.3193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7096   -0.2174    1.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778    0.7704    1.8762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -1.2927    2.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420    0.0378    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3296    0.9594    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150    1.3098    1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613    2.4404    0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.6542   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571   -2.5509   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -3.6063   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -2.0108   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -0.6689    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.0648    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0487   -1.1446   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757    2.8924   -1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649    2.9473   -1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3957    1.9457   -2.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2447   -0.4703   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621   -1.9645    2.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743    1.0692    0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
 13 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  2  0
 21  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(N-Acetyl-L-cystein-S-yl)acetaminophen	ChEBI
Acetaminophen mercapturic acid	ChEBI
Acetaminophen N-acetyl-L-cysteine conjugate	ChEBI
N-Acetyl-L-cysteine S-acetaminophen conjugate	ChEBI
N-Acetyl-L-cysteine S-paracetamol conjugate	ChEBI
N-Acetyl-S-(5-(acetylamino)-2-hydroxyphenyl)-L-cysteine	ChEBI
Paracetamol N-acetyl-L-cysteine conjugate	ChEBI
Acetaminophen mercaptate	Generator
Acetaminophen mercaptic acid	Generator
Acetaminophen N-acetyl-L-cysteine conjugic acid	Generator
N-Acetyl-L-cysteine S-acetaminophen conjugic acid	Generator
N-Acetyl-L-cysteine S-paracetamol conjugic acid	Generator
Paracetamol N-acetyl-L-cysteine conjugic acid	Generator
Acetaminophen mercapturate monopotassium salt	HMDB
Paracetamol mercapturate	HMDB

Chemical Formula

C₁₃H₁₆N₂O₅S

Average Molecular Weight

312.34

Monoisotopic Molecular Weight

312.077992797

IUPAC Name

(2R)-3-({2-hydroxy-5-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)-2-[(1-hydroxyethylidene)amino]propanoic acid

Traditional Name

(2R)-3-({2-hydroxy-5-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)-2-[(1-hydroxyethylidene)amino]propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CSC1=C(O)C=CC(=C1)N=C(C)O)(N=C(C)O)C(O)=O

InChI Identifier

InChI=1S/C13H16N2O5S/c1-7(16)14-9-3-4-11(18)12(5-9)21-6-10(13(19)20)15-8(2)17/h3-5,10,18H,6H2,1-2H3,(H,14,16)(H,15,17)(H,19,20)/t10-/m0/s1

InChI Key

DVPRQNKJGQEICH-JTQLQIEISA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Acetanilide
Anilide
N-acetylarylamine
Thiophenol ether
N-arylamide
Aryl thioether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkylarylthioether
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid
Sulfenyl compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	0.85	ALOGPS
logP	1.39	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	1.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	122.71 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.36 m³·mol⁻¹	ChemAxon
Polarizability	30.98 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]+	169.999	30932474
DeepCCS	[M-H]-	167.641	30932474
DeepCCS	[M-2H]-	201.219	30932474
DeepCCS	[M+Na]+	176.446	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.8401 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1068.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	272.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	310.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	231.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	610.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	242.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	849.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	231.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	205.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetaminophen mercapturate	[H][C@@](CSC1=C(O)C=CC(=C1)N=C(C)O)(N=C(C)O)C(O)=O	3950.1	Standard polar	33892256
Acetaminophen mercapturate	[H][C@@](CSC1=C(O)C=CC(=C1)N=C(C)O)(N=C(C)O)C(O)=O	3005.9	Standard non polar	33892256
Acetaminophen mercapturate	[H][C@@](CSC1=C(O)C=CC(=C1)N=C(C)O)(N=C(C)O)C(O)=O	2858.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetaminophen mercapturate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-6390000000-e2014eb87e56bdbd4f34	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetaminophen mercapturate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen mercapturate 10V, Positive-QTOF	splash10-03di-0597000000-0fc8c89e9f5983f9396e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen mercapturate 20V, Positive-QTOF	splash10-0kal-1920000000-cc5f6b1e811c542f45a7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen mercapturate 40V, Positive-QTOF	splash10-0a5c-5900000000-744968e2a59bf8442a41	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen mercapturate 10V, Negative-QTOF	splash10-0019-0911000000-f0a439c284767d6c9c8c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen mercapturate 20V, Negative-QTOF	splash10-03dr-0900000000-14abab8d0a6ab51b1927	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen mercapturate 40V, Negative-QTOF	splash10-000i-6900000000-169732855534bb55ed89	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

75765

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83967

PDB ID

Not Available

ChEBI ID

133435

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

Kong SW, Hernandez-Ferrer C: Assessment of coverage for endogenous metabolites and exogenous chemical compounds using an untargeted metabolomics platform. Pac Symp Biocomput. 2020;25:587-598. [PubMed:31797630 ]

Showing metabocard for Acetaminophen mercapturate (HMDB0242140)

MOL for HMDB0242140 (Acetaminophen mercapturate)

3D MOL for HMDB0242140 (Acetaminophen mercapturate)

3D SDF for HMDB0242140 (Acetaminophen mercapturate)

3D-SDF for HMDB0242140 (Acetaminophen mercapturate)

PDB for HMDB0242140 (Acetaminophen mercapturate)

3D PDB for HMDB0242140 (Acetaminophen mercapturate)

SMILES for HMDB0242140 (Acetaminophen mercapturate)

INCHI for HMDB0242140 (Acetaminophen mercapturate)

Structure for HMDB0242140 (Acetaminophen mercapturate)

3D Structure for HMDB0242140 (Acetaminophen mercapturate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra