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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-02-26 21:23:26 UTC

HMDB ID

HMDB0001504

Secondary Accession Numbers

HMDB01504

Metabolite Identification

Common Name

Aminoparathion

Description

Aminoparathion, also known as e 605 reduced or parathion amino, belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group. Aminoparathion has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make aminoparathion a potential biomarker for the consumption of these foods. Aminoparathion is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Aminoparathion.

Structure

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

HMDB0001504
     RDKit          3D
Aminoparathion
 32 32  0  0  0  0  0  0  0  0999 V2000
   -1.7668    3.6533   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670    2.1930   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854    1.4136   -0.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -0.1749   -0.3841 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0303   -0.4111   -1.9574 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -0.7167    0.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414   -1.4873    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1620   -2.9099    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683   -1.1721   -0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3731   -0.8393   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.7706    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343   -0.4276    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9858   -0.1573    0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3620    0.1860    0.4119 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906   -0.2094   -1.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -0.5567   -1.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820    3.8636   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8111    4.1718    0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    4.1272   -1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6523    1.9646    0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6224    1.8554   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077   -1.1371    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873   -1.2968   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163   -3.3712    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1366   -2.9814    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -3.4991   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279   -1.0085    2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612   -0.4027    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8595    0.8288   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9227   -0.1625    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.0288   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.5940   -2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv0541 02231219112D          

 16 16  0  0  0  0            999 V2000
    0.5738   -0.3779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -0.7902    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2849    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554   -0.3779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1409   -1.6147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7214   -1.3742    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443    1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2849    1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701   -0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703    2.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881   -0.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -2.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    2.9271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 10 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001504

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=S)(OCC)OC1=CC=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16NO3PS/c1-3-12-15(16,13-4-2)14-10-7-5-9(11)6-8-10/h5-8H,3-4,11H2,1-2H3

> <INCHI_KEY>
XIZOTXGJXSTQDI-UHFFFAOYSA-N

> <FORMULA>
C10H16NO3PS

> <MOLECULAR_WEIGHT>
261.278

> <EXACT_MASS>
261.058850585

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.99507501437565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O-4-aminophenyl O,O-diethyl phosphorothioate

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.5462963336666666

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.8638276789341712

> <JCHEM_POLAR_SURFACE_AREA>
53.71

> <JCHEM_REFRACTIVITY>
70.06490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-4-aminophenyl O,O-diethyl phosphorothioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001504
     RDKit          3D
Aminoparathion
 32 32  0  0  0  0  0  0  0  0999 V2000
   -1.7668    3.6533   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670    2.1930   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854    1.4136   -0.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -0.1749   -0.3841 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0303   -0.4111   -1.9574 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -0.7167    0.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414   -1.4873    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1620   -2.9099    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683   -1.1721   -0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3731   -0.8393   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.7706    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343   -0.4276    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9858   -0.1573    0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3620    0.1860    0.4119 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906   -0.2094   -1.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -0.5567   -1.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820    3.8636   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8111    4.1718    0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    4.1272   -1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6523    1.9646    0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6224    1.8554   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077   -1.1371    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873   -1.2968   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163   -3.3712    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1366   -2.9814    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -3.4991   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279   -1.0085    2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612   -0.4027    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8595    0.8288   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9227   -0.1625    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.0288   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.5940   -2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       1.071  -0.705   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.065   0.840   0.000  0.00  0.00           C+0
HETATM    3  P   UNK     0      -0.269  -1.475   0.000  0.00  0.00           P+0
HETATM    4  C   UNK     0      -0.269   1.616   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.398   1.616   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.597  -0.705   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.263  -3.014   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0      -1.347  -2.565   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0      -0.269   3.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.398   3.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.931  -1.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.071  -3.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.065   3.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.271  -0.712   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.077  -5.329   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.071   5.464   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1    6    7    8                                             
CONECT    4    2    9                                                       
CONECT    5    2   10                                                       
CONECT    6    3   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3                                                            
CONECT    9    4   13                                                       
CONECT   10    5   13                                                       
CONECT   11    6   14                                                       
CONECT   12    7   15                                                       
CONECT   13    9   16   10                                                  
CONECT   14   11                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001504
HETATM    1  C1  UNL     1      -1.767   3.653  -0.422  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.067   2.193  -0.327  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.885   1.414  -0.265  1.00  0.00           O  
HETATM    4  P1  UNL     1      -1.277  -0.175  -0.384  1.00  0.00           P  
HETATM    5  S1  UNL     1      -2.030  -0.411  -1.957  1.00  0.00           S  
HETATM    6  O2  UNL     1      -2.356  -0.717   0.830  1.00  0.00           O  
HETATM    7  C3  UNL     1      -3.341  -1.487   0.160  1.00  0.00           C  
HETATM    8  C4  UNL     1      -3.162  -2.910   0.622  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.068  -1.172  -0.309  1.00  0.00           O  
HETATM   10  C5  UNL     1       1.373  -0.839  -0.086  1.00  0.00           C  
HETATM   11  C6  UNL     1       1.900  -0.771   1.172  1.00  0.00           C  
HETATM   12  C7  UNL     1       3.234  -0.428   1.362  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.986  -0.157   0.256  1.00  0.00           C  
HETATM   14  N1  UNL     1       5.362   0.186   0.412  1.00  0.00           N  
HETATM   15  C9  UNL     1       3.491  -0.209  -1.015  1.00  0.00           C  
HETATM   16  C10 UNL     1       2.155  -0.557  -1.219  1.00  0.00           C  
HETATM   17  H1  UNL     1      -0.782   3.864  -0.911  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.811   4.172   0.549  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.584   4.127  -1.060  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.652   1.965   0.604  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.622   1.855  -1.206  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.308  -1.137   0.693  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.487  -1.297  -0.861  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.916  -3.371   1.199  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.137  -2.981   1.149  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.918  -3.499  -0.333  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.328  -1.009   2.094  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.661  -0.403   2.348  1.00  0.00           H  
HETATM   29  H13 UNL     1       5.860   0.829  -0.277  1.00  0.00           H  
HETATM   30  H14 UNL     1       5.923  -0.163   1.213  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.087   0.029  -1.864  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.677  -0.594  -2.168  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4
CONECT    4    5    5    6    9
CONECT    6    7
CONECT    7    8   22   23
CONECT    8   24   25   26
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   15
CONECT   14   29   30
CONECT   15   16   16   31
CONECT   16   32
END

HMDB0001504
     RDKit          3D
Aminoparathion
 32 32  0  0  0  0  0  0  0  0999 V2000
   -1.7668    3.6533   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670    2.1930   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854    1.4136   -0.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -0.1749   -0.3841 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0303   -0.4111   -1.9574 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -0.7167    0.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414   -1.4873    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1620   -2.9099    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683   -1.1721   -0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3731   -0.8393   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.7706    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343   -0.4276    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9858   -0.1573    0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3620    0.1860    0.4119 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906   -0.2094   -1.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -0.5567   -1.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820    3.8636   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8111    4.1718    0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    4.1272   -1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6523    1.9646    0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6224    1.8554   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077   -1.1371    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873   -1.2968   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163   -3.3712    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1366   -2.9814    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -3.4991   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279   -1.0085    2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612   -0.4027    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8595    0.8288   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9227   -0.1625    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.0288   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.5940   -2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Aminoparathion	ChEBI
Amino-parathion	ChEBI
e 605 Reduced	ChEBI
O,O-Diethyl O-(4-aminophenyl) phosphorothioate	ChEBI
p-Aminoparathion	ChEBI
Parathion amino	ChEBI
Phosphorothioic acid, O-(4-aminophenyl) O,O-diethyl ester	ChEBI
Thiophosphoric acid diethyl 4-aminophenyl ester	ChEBI
Thiophosphoric acid O-(4-aminophenyl) O,O-diethyl ester	ChEBI
O,O-Diethyl O-(4-aminophenyl) phosphorothioic acid	Generator
Phosphorothioate, O-(4-aminophenyl) O,O-diethyl ester	Generator
Thiophosphate diethyl 4-aminophenyl ester	Generator
Thiophosphate O-(4-aminophenyl) O,O-diethyl ester	Generator
AP	HMDB

Chemical Formula

C₁₀H₁₆NO₃PS

Average Molecular Weight

261.278

Monoisotopic Molecular Weight

261.058850585

IUPAC Name

O-4-aminophenyl O,O-diethyl phosphorothioate

Traditional Name

O-4-aminophenyl O,O-diethyl phosphorothioate

CAS Registry Number

3735-01-1

SMILES

CCOP(=S)(OCC)OC1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C10H16NO3PS/c1-3-12-15(16,13-4-2)14-10-7-5-9(11)6-8-10/h5-8H,3-4,11H2,1-2H3

InChI Key

XIZOTXGJXSTQDI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Phenyl thiophosphates

Alternative Parents

Substituents

Phenyl thiophosphate
Phenoxy compound
Aniline or substituted anilines
Thiophosphate triester
Benzenoid
Monocyclic benzene moiety
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organothiophosphate insecticide (CHEBI:28055 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0001504)
Cell membrane (HMDB: HMDB0001504)

Source

Endogenous

Endogenous (HMDB: HMDB0001504)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.39 mg/mL	Not Available
LogP	2.60	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.55	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	3.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.71 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.06 m³·mol⁻¹	ChemAxon
Polarizability	26 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
DarkChem	[M+H]+	158.044	31661259
DarkChem	[M-H]-	154.707	31661259
AllCCS	[M+H]+	155.292	32859911
AllCCS	[M-H]-	156.003	32859911
DeepCCS	[M+H]+	152.327	30932474
DeepCCS	[M-H]-	149.969	30932474
DeepCCS	[M-2H]-	183.435	30932474
DeepCCS	[M+Na]+	158.421	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	152.0	32859911
AllCCS	[M+NH4]+	158.4	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	157.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.67 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1974.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	515.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	302.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	158.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	564.8 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	645.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1359.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	425.5 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	1213.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	448.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	423.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.1 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	29.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aminoparathion	CCOP(=S)(OCC)OC1=CC=C(N)C=C1	3033.9	Standard polar	33892256
Aminoparathion	CCOP(=S)(OCC)OC1=CC=C(N)C=C1	1919.1	Standard non polar	33892256
Aminoparathion	CCOP(=S)(OCC)OC1=CC=C(N)C=C1	1948.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aminoparathion,1TMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C)C=C1	2028.1	Semi standard non polar	33892256
Aminoparathion,1TMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C)C=C1	2058.6	Standard non polar	33892256
Aminoparathion,1TMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C)C=C1	2535.8	Standard polar	33892256
Aminoparathion,2TMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2052.2	Semi standard non polar	33892256
Aminoparathion,2TMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2176.4	Standard non polar	33892256
Aminoparathion,2TMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2445.4	Standard polar	33892256
Aminoparathion,1TBDMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2260.0	Semi standard non polar	33892256
Aminoparathion,1TBDMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2269.3	Standard non polar	33892256
Aminoparathion,1TBDMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2642.7	Standard polar	33892256
Aminoparathion,2TBDMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2502.3	Semi standard non polar	33892256
Aminoparathion,2TBDMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2568.1	Standard non polar	33892256
Aminoparathion,2TBDMS,isomer #1	CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2682.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aminoparathion GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-3590000000-d03ad6e6ed9919f1c63d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminoparathion 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 - Aminoparathion 10V, Positive-QTOF	splash10-03e9-0090000000-c545df9bf2db240673a7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Positive-QTOF	splash10-0bu0-1290000000-ecfc9bd4e21c704d6f94	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Positive-QTOF	splash10-017i-9230000000-0d34427339291f69a22d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 10V, Negative-QTOF	splash10-03e9-0190000000-3b1135825ef7c95e695f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Negative-QTOF	splash10-01q9-1390000000-1067d2108fe36b18e7d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Negative-QTOF	splash10-0f79-0970000000-625ce950eeb267e2a4bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 10V, Positive-QTOF	splash10-03di-0090000000-d3a3945fd8a4ffa895a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Positive-QTOF	splash10-0bu0-1290000000-cce2f1cb680508f19d13	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Positive-QTOF	splash10-014l-9210000000-f58785b7a936b66d0137	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 10V, Negative-QTOF	splash10-03di-0190000000-ea30c70ed229458b486b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Negative-QTOF	splash10-0089-0790000000-34019406437ef5d82d01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Negative-QTOF	splash10-0ab9-0900000000-239d97e2d83e127ce516	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB022660

KNApSAcK ID

Not Available

Chemspider ID

215

KEGG Compound ID

C06605

BioCyc ID

AMINO-PARATHION

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6284

PubChem Compound

220

PDB ID

Not Available

ChEBI ID

28055

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Rung, Bruno; Schwack, Wolfgang. Aminoparathion: A highly reactive metabolite of parathion. 1. Reactions with polyphenols and polyphenol oxidase. Journal of Agricultural and Food Chemistry (2005), 53(23), 9140-9145.

Material Safety Data Sheet (MSDS)

Not Available

General References

Katan J, Fuhremann TW, Lichtenstein EP: Binding of (14C) parathion in soil: a reassessment of pesticide persistence. Science. 1976 Sep 3;193(4256):891-4. [PubMed:948750 ]
Gorder GW, Lichtenstein EP: Degradation of parathion in culture by microorganisms found in cranberry bogs. Can J Microbiol. 1980 Apr;26(4):475-81. [PubMed:7378942 ]
Lichtenstein EP, Fuhremann TW: Activity of an NADPH-dependent nitroreductase in houseflies. Science. 1971 May 7;172(3983):589-91. [PubMed:4396637 ]
Wehr K: [Detection of E 605 several years after burial]. Z Rechtsmed. 1986;96(1):57-66. [PubMed:3716649 ]
Houx NW, Dekker A: A test system for the determining of the fate of pesticides in surface water. Protocol and comparison of the performance for parathion of ecocores and micro ecosystems from two sources. Int J Environ Anal Chem. 1987;29(1-2):37-59. [PubMed:3570605 ]
Kawar NS, Gunther FA, Iwata Y: Fate of parathion in artificially fortified grape juice processed into wine. J Environ Sci Health B. 1978;13(1):1-9. [PubMed:632538 ]
Jimenez JJ, Bernal JL, del Nozal MJ, Toribio L, Bernal J: Determination of impurities in pesticides and their degradation products formed during the wine-making process by solid-phase extraction and gas chromatography with detection by electron ionization mass spectrometry. II. Bromopropylate, trichlorphon, parathion-methyl and tebuconazole. Rapid Commun Mass Spectrom. 2004;18(22):2629-36. [PubMed:15481093 ]
Zhao X, Hwang HM: A study of the degradation of organophosphorus pesticides in river waters and the identification of their degradation products by chromatography coupled with mass spectrometry. Arch Environ Contam Toxicol. 2009 May;56(4):646-53. doi: 10.1007/s00244-008-9220-8. Epub 2008 Aug 28. [PubMed:18752016 ]
Banna AA, Kawar NS: Behavior of parathion in apple juice processed into cider and vinegar. J Environ Sci Health B. 1982;17(5):505-14. [PubMed:7175099 ]
Muhammad MA, Kawar NS: Behavior of parathion in tomatoes processed into juice and ketchup. J Environ Sci Health B. 1985 Oct;20(5):499-510. [PubMed:4078230 ]
Chan LT, Crowley RJ, Geyer R: Detection and analysis of aminoparathion in human postmortem specimens. J Forensic Sci. 1983 Jan;28(1):122-7. [PubMed:6680731 ]
Munnecke DM, Hsieh DP: Pathways of microbial metabolism of parathion. Appl Environ Microbiol. 1976 Jan;31(1):63-9. [PubMed:8005 ]
Rung B, Schwack W: Aminoparathion: a highly reactive metabolite of parathion. 1. Reactions with polyphenols and polyphenol oxidase. J Agric Food Chem. 2005 Nov 16;53(23):9140-5. [PubMed:16277414 ]

Showing metabocard for Aminoparathion (HMDB0001504)

MOL for HMDB0001504 (Aminoparathion)

3D MOL for HMDB0001504 (Aminoparathion)

3D SDF for HMDB0001504 (Aminoparathion)

3D-SDF for HMDB0001504 (Aminoparathion)

PDB for HMDB0001504 (Aminoparathion)

3D PDB for HMDB0001504 (Aminoparathion)

SMILES for HMDB0001504 (Aminoparathion)

INCHI for HMDB0001504 (Aminoparathion)

Structure for HMDB0001504 (Aminoparathion)

3D Structure for HMDB0001504 (Aminoparathion)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra