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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:30:39 UTC

Update Date

2021-09-26 23:04:08 UTC

HMDB ID

HMDB0251870

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate

Description

EPN belongs to the class of organic compounds known as phenyl phenylphosphonothioates. These are aromatic compounds containing a phenylphosphonothioate group, which is O-esterified with another phenyl group. They have the general structure OP(R)(=S)OR', where R,R'=phenyl groups. EPN is possibly neutral. This compound has been identified in human blood as reported by (PMID: 31557052 ). O-ethyl o-(4-nitrophenyl) phenylphosphonothioate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0251870
     RDKit          3D
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.3017    4.1165   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3922    2.8846   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1098    1.7796   -0.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670    0.4475   -0.5766 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.3881    0.2021   -2.1415 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    0.7290    0.5929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847    0.3453    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629   -0.8963    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634   -1.2934    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565   -0.4071   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5017   -0.7780   -0.3053 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.9468   -1.8876    0.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415    0.1164   -0.9012 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.7071    0.8431   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3938    1.1918   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440   -1.0459   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645   -0.9646    0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161   -2.1278    0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2921   -3.3467    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860   -3.4617   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -2.2869   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    3.9026   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786    4.3971    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8237    4.9581   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673    3.0878   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    2.7271    0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -1.6141    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6306   -2.2753    0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4040    1.5501   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0419    2.1701   -0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    0.0254    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7585   -2.0481    1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7798   -4.2963    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -4.4193   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4827   -2.3250   -0.9271 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  8 27  1  0
  9 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  CHG  2  11   1  13  -1
M  END


  Mrv1572004191601192D          

 21 22  0  0  0  0            999 V2000
    4.3974    2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.2211    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.2211    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  2  0  0  0  0
 18  2  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251870

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14NO4PS/c1-2-18-20(21,14-6-4-3-5-7-14)19-13-10-8-12(9-11-13)15(16)17/h3-11H,2H2,1H3

> <INCHI_KEY>
AIGRXSNSLVJMEA-UHFFFAOYSA-N

> <FORMULA>
C14H14NO4PS

> <MOLECULAR_WEIGHT>
323.3

> <EXACT_MASS>
323.038116107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.966565601341628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O-ethyl O-4-nitrophenyl phenylphosphonothioate

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
4.646199999999999

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
64.28

> <JCHEM_REFRACTIVITY>
86.05280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.90e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
santox

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251870
     RDKit          3D
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.3017    4.1165   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3922    2.8846   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1098    1.7796   -0.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670    0.4475   -0.5766 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.3881    0.2021   -2.1415 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    0.7290    0.5929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847    0.3453    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629   -0.8963    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634   -1.2934    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565   -0.4071   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5017   -0.7780   -0.3053 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.9468   -1.8876    0.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415    0.1164   -0.9012 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.7071    0.8431   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3938    1.1918   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440   -1.0459   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645   -0.9646    0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161   -2.1278    0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2921   -3.3467    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860   -3.4617   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -2.2869   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    3.9026   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786    4.3971    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8237    4.9581   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673    3.0878   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    2.7271    0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -1.6141    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6306   -2.2753    0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4040    1.5501   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0419    2.1701   -0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    0.0254    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7585   -2.0481    1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7798   -4.2963    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -4.4193   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4827   -2.3250   -0.9271 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  8 27  1  0
  9 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  CHG  2  11   1  13  -1
M  END

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       8.208   4.263   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.208   2.723   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.875  -4.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.208  -3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.541  -3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.208  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.541  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.255   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.565   4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.025   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.025   4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.565   1.746   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.875  -1.127   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.255   5.747   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.715   5.747   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.025   7.081   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.875   1.953   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.413   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       6.875   0.413   0.000  0.00  0.00           P+0
HETATM   21  S   UNK     0       8.415   0.413   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1   18                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   14                                                       
CONECT    7    5   14                                                       
CONECT    8   10   12                                                       
CONECT    9   11   12                                                       
CONECT   10    8   13                                                       
CONECT   11    9   13                                                       
CONECT   12    8    9   15                                                  
CONECT   13   10   11   19                                                  
CONECT   14    6    7   20                                                  
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2   20                                                       
CONECT   19   13   20                                                       
CONECT   20   14   18   19   21                                             
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0251870
HETATM    1  C1  UNL     1      -2.302   4.116  -0.155  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.392   2.885  -0.154  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.110   1.780  -0.595  1.00  0.00           O  
HETATM    4  P1  UNL     1      -1.067   0.448  -0.577  1.00  0.00           P  
HETATM    5  S1  UNL     1      -0.388   0.202  -2.141  1.00  0.00           S  
HETATM    6  O2  UNL     1       0.153   0.729   0.593  1.00  0.00           O  
HETATM    7  C3  UNL     1       1.485   0.345   0.373  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.963  -0.896   0.738  1.00  0.00           C  
HETATM    9  C5  UNL     1       3.263  -1.293   0.531  1.00  0.00           C  
HETATM   10  C6  UNL     1       4.156  -0.407  -0.076  1.00  0.00           C  
HETATM   11  N1  UNL     1       5.502  -0.778  -0.305  1.00  0.00           N1+
HETATM   12  O3  UNL     1       5.947  -1.888   0.016  1.00  0.00           O  
HETATM   13  O4  UNL     1       6.341   0.116  -0.901  1.00  0.00           O1-
HETATM   14  C7  UNL     1       3.707   0.843  -0.453  1.00  0.00           C  
HETATM   15  C8  UNL     1       2.394   1.192  -0.223  1.00  0.00           C  
HETATM   16  C9  UNL     1      -1.944  -1.046  -0.114  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.164  -0.965   0.553  1.00  0.00           C  
HETATM   18  C11 UNL     1      -3.816  -2.128   0.896  1.00  0.00           C  
HETATM   19  C12 UNL     1      -3.292  -3.347   0.596  1.00  0.00           C  
HETATM   20  C13 UNL     1      -2.086  -3.462  -0.064  1.00  0.00           C  
HETATM   21  C14 UNL     1      -1.447  -2.287  -0.400  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.250   3.903  -0.695  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.479   4.397   0.907  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.824   4.958  -0.695  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.567   3.088  -0.875  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.926   2.727   0.831  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.290  -1.614   1.215  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.631  -2.275   0.823  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.404   1.550  -0.933  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.042   2.170  -0.518  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.553   0.025   0.777  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.758  -2.048   1.412  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.780  -4.296   0.852  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.649  -4.419  -0.313  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.483  -2.325  -0.927  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4
CONECT    4    5    5    6   16
CONECT    6    7
CONECT    7    8    8   15
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   14
CONECT   11   12   12   13
CONECT   14   15   15   29
CONECT   15   30
CONECT   16   17   17   21
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   21   34
CONECT   21   35
END

HMDB0251870
     RDKit          3D
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.3017    4.1165   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3922    2.8846   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1098    1.7796   -0.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670    0.4475   -0.5766 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.3881    0.2021   -2.1415 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    0.7290    0.5929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847    0.3453    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629   -0.8963    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634   -1.2934    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565   -0.4071   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5017   -0.7780   -0.3053 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.9468   -1.8876    0.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415    0.1164   -0.9012 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.7071    0.8431   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3938    1.1918   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440   -1.0459   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645   -0.9646    0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161   -2.1278    0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2921   -3.3467    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860   -3.4617   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -2.2869   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    3.9026   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786    4.3971    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8237    4.9581   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673    3.0878   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    2.7271    0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -1.6141    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6306   -2.2753    0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4040    1.5501   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0419    2.1701   -0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    0.0254    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7585   -2.0481    1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7798   -4.2963    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -4.4193   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4827   -2.3250   -0.9271 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  8 27  1  0
  9 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  CHG  2  11   1  13  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl p-nitrophenyl benzenethionophosphonate	ChEBI
O-Ethyl O-(4-nitrophenyl)phenylphosphonothioate	ChEBI
O-Ethyl O-(p-nitrophenyl) phenylphosphonothioate	ChEBI
O-Ethyl O-p-nitrophenyl phenylphosphonothioate	ChEBI
O-Ethyl phenylphosphonothioic acid O-(4-nitrophenyl) ester	ChEBI
Ethyl p-nitrophenyl benzenethionophosphonic acid	Generator
O-Ethyl O-(4-nitrophenyl)phenylphosphonothioic acid	Generator
O-Ethyl O-(p-nitrophenyl) phenylphosphonothioic acid	Generator
O-Ethyl O-p-nitrophenyl phenylphosphonothioic acid	Generator
O-Ethyl phenylphosphonothioate O-(4-nitrophenyl) ester	Generator
Ethoxy-(4-nitrophenoxy)-phenyl-sulphanylidene-$l^{5}-phosphane	Generator
Phenylphosphonothioic acid, 2-ethyl 2-(4-nitrophenyl) ester	MeSH
EPN-300	MeSH
O-Ethyl-O-(4-nitrophenyl)phenylphosphonothioate	MeSH
EPN 300	MeSH

Chemical Formula

C₁₄H₁₄NO₄PS

Average Molecular Weight

323.3

Monoisotopic Molecular Weight

323.038116107

IUPAC Name

O-ethyl O-4-nitrophenyl phenylphosphonothioate

Traditional Name

santox

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H14NO4PS/c1-2-18-20(21,14-6-4-3-5-7-14)19-13-10-8-12(9-11-13)15(16)17/h3-11H,2H2,1H3

InChI Key

AIGRXSNSLVJMEA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl phenylphosphonothioates. These are aromatic compounds containing a phenylphosphonothioate group, which is O-esterified with another phenyl group. They have the general structure OP(R)(=S)OR', where R,R'=phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylphosphonothioates

Direct Parent

Phenyl phenylphosphonothioates

Alternative Parents

Substituents

Phenyl phenylphosphonothioate
Phenyl ethylphosphonothioate
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organothiophosphorus compound
Allyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organic phosphonate (CHEBI:34733 )
phosphonic ester (CHEBI:34733 )
organothiophosphate insecticide (CHEBI:34733 )
Organophosphorus insecticides (C14434 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.88	ALOGPS
logP	4.65	ChemAxon
logS	-5.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	64.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	86.05 m³·mol⁻¹	ChemAxon
Polarizability	30.97 Å³	ChemAxon
Number of Rings	2	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]+	167.721	30932474
DeepCCS	[M-H]-	165.363	30932474
DeepCCS	[M-2H]-	198.675	30932474
DeepCCS	[M+Na]+	173.902	30932474
AllCCS	[M+H]+	169.1	32859911
AllCCS	[M+H-H2O]+	166.1	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.7	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	17.1118 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2509.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	619.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	242.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	350.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	771.2 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	660.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1637.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	634.9 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	1566.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	542.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	498.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	471.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	579.5 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	12.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate	CCOP(=S)(OC1=CC=C(C=C1)N(=O)=O)C1=CC=CC=C1	3606.3	Standard polar	33892256
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate	CCOP(=S)(OC1=CC=C(C=C1)N(=O)=O)C1=CC=CC=C1	2365.2	Standard non polar	33892256
O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate	CCOP(=S)(OC1=CC=C(C=C1)N(=O)=O)C1=CC=CC=C1	2410.5	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 - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002n-2691000000-3e634e3980f6225283dd	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 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 - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 10V, Positive-QTOF	splash10-00di-1009000000-6dab6913d736f84cc794	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 20V, Positive-QTOF	splash10-05j0-9138000000-5535ee984b6767374052	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 40V, Positive-QTOF	splash10-0032-9500000000-d8e4d63ad369694b3a32	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 10V, Negative-QTOF	splash10-00di-0009000000-12ffbc59e9a84be07e92	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 20V, Negative-QTOF	splash10-0fk9-3109000000-8b7ac2191473ada66e49	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 40V, Negative-QTOF	splash10-01sl-6961000000-5ea6ee5bbbcfd18c71e2	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14434

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

EPN

METLIN ID

Not Available

PubChem Compound

16421

PDB ID

Not Available

ChEBI ID

34733

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate (HMDB0251870)

MOL for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

3D MOL for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

3D SDF for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

3D-SDF for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

PDB for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

3D PDB for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

SMILES for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

INCHI for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

Structure for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

3D Structure for HMDB0251870 (O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra