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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 16:49:40 UTC

Update Date

2021-09-14 14:57:39 UTC

HMDB ID

HMDB0060559

Secondary Accession Numbers

HMDB60559

Metabolite Identification

Common Name

Acetaminophen cystein

Description

Acetaminophen cystein, also known as paracetamol cysteine or aa-cysteine, belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. Acetaminophen cystein is a very strong basic compound (based on its pKa). Within humans, acetaminophen cystein participates in a number of enzymatic reactions. In particular, acetaminophen cystein can be biosynthesized from NAPQI and glutathione through its interaction with the enzymes glutathione S-transferase p and glutathione S-transferase theta-1. In addition, acetaminophen cystein can be converted into acetaminophen cystein through its interaction with the enzyme multidrug resistance-associated protein 1. In humans, acetaminophen cystein is involved in acetaminophen metabolism pathway.

Structure

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

HMDB0060559
     RDKit          3D
Acetaminophen cystein
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.9024   -2.9755    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823   -1.5674    1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649   -0.5319    2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -1.5271    1.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118   -0.8357    0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078   -0.7664   -0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -0.0832   -0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343    0.5558    0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992    1.4315   -0.4176 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973    0.2511   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    1.0260   -0.6870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0077    1.4494   -2.0546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    2.2149    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    2.1638    1.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844    3.4751   -0.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315    0.5113    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3390   -0.1739    1.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288   -2.9623    2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -3.6710    1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -3.0733    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0876   -0.5983    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129   -1.2935   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813   -0.0246   -1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690   -0.6203   -0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1001   -0.0458    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443    0.3853   -0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    2.1535   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7391    0.6494   -2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    3.6589   -1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    1.0288    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -0.2046    2.8040 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 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
  3 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv0541 06151309492D          

 17 17  0  0  0  0            999 V2000
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11 10  1  0  0  0  0
 10 12  1  6  0  0  0
 13  7  2  0  0  0  0
 13  8  1  4  0  0  0
 14  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 17  6  1  0  0  0  0
 17  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060559

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)=NC1=CC=C(SC[C@H](N)C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O3S/c1-7(14)13-8-2-4-9(5-3-8)17-6-10(12)11(15)16/h2-5,10H,6,12H2,1H3,(H,13,14)(H,15,16)/t10-/m0/s1

> <INCHI_KEY>
ZOZXXYPCOKGXOE-JTQLQIEISA-N

> <FORMULA>
C11H14N2O3S

> <MOLECULAR_WEIGHT>
254.305

> <EXACT_MASS>
254.072513014

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.344197638050566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-({4-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)propanoic acid

> <ALOGPS_LOGP>
-1.44

> <JCHEM_LOGP>
-1.0655538496830526

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
6.858706549827192

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8196430449016088

> <JCHEM_PKA_STRONGEST_BASIC>
9.455638472204646

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
68.4179

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-3-({4-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060559
     RDKit          3D
Acetaminophen cystein
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.9024   -2.9755    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823   -1.5674    1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649   -0.5319    2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -1.5271    1.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118   -0.8357    0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078   -0.7664   -0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -0.0832   -0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343    0.5558    0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992    1.4315   -0.4176 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973    0.2511   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    1.0260   -0.6870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0077    1.4494   -2.0546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    2.2149    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    2.1638    1.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844    3.4751   -0.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315    0.5113    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3390   -0.1739    1.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288   -2.9623    2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -3.6710    1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -3.0733    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0876   -0.5983    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129   -1.2935   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813   -0.0246   -1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690   -0.6203   -0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1001   -0.0458    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443    0.3853   -0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    2.1535   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7391    0.6494   -2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    3.6589   -1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    1.0288    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -0.2046    2.8040 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 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
  3 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      13.337   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      14.671  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0       8.002  -3.080   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   17                                                       
CONECT    7    1   13   14                                                  
CONECT    8    2    3   13                                                  
CONECT    9    4    5   17                                                  
CONECT   10    6   11   12                                                  
CONECT   11   10   15   16                                                  
CONECT   12   10                                                            
CONECT   13    7    8                                                       
CONECT   14    7                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17    6    9                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0060559
HETATM    1  C1  UNL     1       4.902  -2.976   1.746  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.282  -1.567   1.642  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.065  -0.532   2.095  1.00  0.00           O  
HETATM    4  N1  UNL     1       3.183  -1.527   1.175  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.112  -0.836   0.793  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.708  -0.766  -0.543  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.604  -0.083  -0.917  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.134   0.556   0.050  1.00  0.00           C  
HETATM    9  S1  UNL     1      -1.599   1.431  -0.418  1.00  0.00           S  
HETATM   10  C7  UNL     1      -2.997   0.251  -0.256  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.233   1.026  -0.687  1.00  0.00           C  
HETATM   12  N2  UNL     1      -4.008   1.449  -2.055  1.00  0.00           N  
HETATM   13  C9  UNL     1      -4.301   2.215   0.192  1.00  0.00           C  
HETATM   14  O2  UNL     1      -4.457   2.164   1.435  1.00  0.00           O  
HETATM   15  O3  UNL     1      -4.184   3.475  -0.393  1.00  0.00           O  
HETATM   16  C10 UNL     1       0.231   0.511   1.383  1.00  0.00           C  
HETATM   17  C11 UNL     1       1.339  -0.174   1.752  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.429  -2.962   2.718  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.060  -3.671   1.789  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.567  -3.073   0.876  1.00  0.00           H  
HETATM   21  H4  UNL     1       6.088  -0.598   2.067  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.313  -1.294  -1.297  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.281  -0.025  -1.968  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.869  -0.620  -0.926  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.100  -0.046   0.823  1.00  0.00           H  
HETATM   26  H9  UNL     1      -5.144   0.385  -0.605  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.239   2.154  -2.120  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.739   0.649  -2.677  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.398   3.659  -1.378  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.376   1.029   2.145  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.616  -0.205   2.804  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    4
CONECT    3   21
CONECT    4    5
CONECT    5    6    6   17
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   16
CONECT    9   10
CONECT   10   11   24   25
CONECT   11   12   13   26
CONECT   12   27   28
CONECT   13   14   14   15
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   31
END

HMDB0060559
     RDKit          3D
Acetaminophen cystein
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.9024   -2.9755    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823   -1.5674    1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649   -0.5319    2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -1.5271    1.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118   -0.8357    0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078   -0.7664   -0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -0.0832   -0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343    0.5558    0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992    1.4315   -0.4176 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973    0.2511   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    1.0260   -0.6870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0077    1.4494   -2.0546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    2.2149    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    2.1638    1.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844    3.4751   -0.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315    0.5113    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3390   -0.1739    1.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288   -2.9623    2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -3.6710    1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -3.0733    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0876   -0.5983    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129   -1.2935   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813   -0.0246   -1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690   -0.6203   -0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1001   -0.0458    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443    0.3853   -0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    2.1535   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7391    0.6494   -2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    3.6589   -1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    1.0288    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -0.2046    2.8040 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 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
  3 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Paracetamol cysteine	HMDB
AA-cysteine	HMDB
Acetaminophen cysteine	MeSH

Chemical Formula

C₁₁H₁₄N₂O₃S

Average Molecular Weight

254.305

Monoisotopic Molecular Weight

254.072513014

IUPAC Name

(2R)-2-amino-3-({4-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)propanoic acid

Traditional Name

(2R)-2-amino-3-({4-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NC1=CC=C(SC[C@H](N)C(O)=O)C=C1

InChI Identifier

InChI=1S/C11H14N2O3S/c1-7(14)13-8-2-4-9(5-3-8)17-6-10(12)11(15)16/h2-5,10H,6,12H2,1H3,(H,13,14)(H,15,16)/t10-/m0/s1

InChI Key

ZOZXXYPCOKGXOE-JTQLQIEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-cysteine-S-conjugates

Alternative Parents

Substituents

L-cysteine-s-conjugate
L-alpha-amino acid
Alpha-amino acid
Acetanilide
N-acetylarylamine
Anilide
N-arylamide
Thiophenol ether
Aryl thioether
Alkylarylthioether
Benzenoid
Monocyclic benzene moiety
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfenyl compound
Thioether
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
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
Water Solubility	0.34 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.1	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	9.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.42 m³·mol⁻¹	ChemAxon
Polarizability	26.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	159.615	31661259
DarkChem	[M-H]-	157.659	31661259
DeepCCS	[M+H]+	158.296	30932474
DeepCCS	[M-H]-	155.938	30932474
DeepCCS	[M-2H]-	188.995	30932474
DeepCCS	[M+Na]+	164.389	30932474
AllCCS	[M+H]+	155.8	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	156.8	32859911
AllCCS	[M+Na-2H]-	157.3	32859911
AllCCS	[M+HCOO]-	157.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetaminophen cystein	CC(O)=NC1=CC=C(SC[C@H](N)C(O)=O)C=C1	3660.2	Standard polar	33892256
Acetaminophen cystein	CC(O)=NC1=CC=C(SC[C@H](N)C(O)=O)C=C1	2497.9	Standard non polar	33892256
Acetaminophen cystein	CC(O)=NC1=CC=C(SC[C@H](N)C(O)=O)C=C1	2517.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetaminophen cystein,1TMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N)C(=O)O)C=C1)O[Si](C)(C)C	2431.6	Semi standard non polar	33892256
Acetaminophen cystein,1TMS,isomer #2	CC(O)=NC1=CC=C(SC[C@H](N)C(=O)O[Si](C)(C)C)C=C1	2430.7	Semi standard non polar	33892256
Acetaminophen cystein,1TMS,isomer #3	CC(O)=NC1=CC=C(SC[C@H](N[Si](C)(C)C)C(=O)O)C=C1	2505.5	Semi standard non polar	33892256
Acetaminophen cystein,2TMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N)C(=O)O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2366.3	Semi standard non polar	33892256
Acetaminophen cystein,2TMS,isomer #2	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C)C(=O)O)C=C1)O[Si](C)(C)C	2415.6	Semi standard non polar	33892256
Acetaminophen cystein,2TMS,isomer #3	CC(O)=NC1=CC=C(SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C=C1	2437.4	Semi standard non polar	33892256
Acetaminophen cystein,2TMS,isomer #4	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2663.2	Semi standard non polar	33892256
Acetaminophen cystein,3TMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2389.2	Semi standard non polar	33892256
Acetaminophen cystein,3TMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2382.6	Standard non polar	33892256
Acetaminophen cystein,3TMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2887.1	Standard polar	33892256
Acetaminophen cystein,3TMS,isomer #2	CC(=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2510.5	Semi standard non polar	33892256
Acetaminophen cystein,3TMS,isomer #2	CC(=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2502.4	Standard non polar	33892256
Acetaminophen cystein,3TMS,isomer #2	CC(=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	3023.9	Standard polar	33892256
Acetaminophen cystein,3TMS,isomer #3	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2562.7	Semi standard non polar	33892256
Acetaminophen cystein,3TMS,isomer #3	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2494.9	Standard non polar	33892256
Acetaminophen cystein,3TMS,isomer #3	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2998.7	Standard polar	33892256
Acetaminophen cystein,4TMS,isomer #1	CC(=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2495.4	Semi standard non polar	33892256
Acetaminophen cystein,4TMS,isomer #1	CC(=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2516.9	Standard non polar	33892256
Acetaminophen cystein,4TMS,isomer #1	CC(=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2747.0	Standard polar	33892256
Acetaminophen cystein,1TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N)C(=O)O)C=C1)O[Si](C)(C)C(C)(C)C	2707.9	Semi standard non polar	33892256
Acetaminophen cystein,1TBDMS,isomer #2	CC(O)=NC1=CC=C(SC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C=C1	2707.2	Semi standard non polar	33892256
Acetaminophen cystein,1TBDMS,isomer #3	CC(O)=NC1=CC=C(SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C=C1	2738.0	Semi standard non polar	33892256
Acetaminophen cystein,2TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2858.1	Semi standard non polar	33892256
Acetaminophen cystein,2TBDMS,isomer #2	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C=C1)O[Si](C)(C)C(C)(C)C	2927.6	Semi standard non polar	33892256
Acetaminophen cystein,2TBDMS,isomer #3	CC(O)=NC1=CC=C(SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1	2910.4	Semi standard non polar	33892256
Acetaminophen cystein,2TBDMS,isomer #4	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3101.4	Semi standard non polar	33892256
Acetaminophen cystein,3TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3078.0	Semi standard non polar	33892256
Acetaminophen cystein,3TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2979.3	Standard non polar	33892256
Acetaminophen cystein,3TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3135.9	Standard polar	33892256
Acetaminophen cystein,3TBDMS,isomer #2	CC(=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3280.7	Semi standard non polar	33892256
Acetaminophen cystein,3TBDMS,isomer #2	CC(=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3065.3	Standard non polar	33892256
Acetaminophen cystein,3TBDMS,isomer #2	CC(=NC1=CC=C(SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3194.6	Standard polar	33892256
Acetaminophen cystein,3TBDMS,isomer #3	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3256.4	Semi standard non polar	33892256
Acetaminophen cystein,3TBDMS,isomer #3	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3076.0	Standard non polar	33892256
Acetaminophen cystein,3TBDMS,isomer #3	CC(O)=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3190.0	Standard polar	33892256
Acetaminophen cystein,4TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3453.8	Semi standard non polar	33892256
Acetaminophen cystein,4TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3220.2	Standard non polar	33892256
Acetaminophen cystein,4TBDMS,isomer #1	CC(=NC1=CC=C(SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3078.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetaminophen cystein GC-MS (Non-derivatized) - 70eV, Positive	splash10-044l-8970000000-5c778be04752360df8ea	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetaminophen cystein GC-MS (2 TMS) - 70eV, Positive	splash10-01c9-9743000000-11992e3486bb1de35597	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetaminophen cystein 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 cystein 10V, Positive-QTOF	splash10-0a4r-1490000000-651187c3825b168ab24d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 20V, Positive-QTOF	splash10-06di-1940000000-c69f3e5dd0de3df47b0e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 40V, Positive-QTOF	splash10-0gic-3900000000-3bb28136fd14a5691177	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 10V, Negative-QTOF	splash10-0uxr-1490000000-1b4f05b101e91fba5e7b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 20V, Negative-QTOF	splash10-01b9-1910000000-55f1adf01057650c3204	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 40V, Negative-QTOF	splash10-0079-9500000000-065b9ad7f744a497808c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 10V, Positive-QTOF	splash10-0a4i-0290000000-2eb94517a0f5def956bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 20V, Positive-QTOF	splash10-0600-0940000000-e234237eb5295baf49c3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 40V, Positive-QTOF	splash10-00xr-5900000000-3c8afec24be499db50c4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 10V, Negative-QTOF	splash10-0uxr-0590000000-3e90f355c619f21ce542	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 20V, Negative-QTOF	splash10-0002-0900000000-0981e7bb446bf549fbd9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetaminophen cystein 40V, Negative-QTOF	splash10-0fk9-1900000000-684281e2191bb07e83d8	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Acetaminophen Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83997

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

Not Available

Showing metabocard for Acetaminophen cystein (HMDB0060559)

MOL for HMDB0060559 (Acetaminophen cystein)

3D MOL for HMDB0060559 (Acetaminophen cystein)

3D SDF for HMDB0060559 (Acetaminophen cystein)

3D-SDF for HMDB0060559 (Acetaminophen cystein)

PDB for HMDB0060559 (Acetaminophen cystein)

3D PDB for HMDB0060559 (Acetaminophen cystein)

SMILES for HMDB0060559 (Acetaminophen cystein)

INCHI for HMDB0060559 (Acetaminophen cystein)

Structure for HMDB0060559 (Acetaminophen cystein)

3D Structure for HMDB0060559 (Acetaminophen cystein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra