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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:46:28 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041893

Secondary Accession Numbers

HMDB41893

Metabolite Identification

Common Name

Fenitrothion

Description

Fenitrothion, also known as metathion or MEP, 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. Based on a literature review a small amount of articles have been published on Fenitrothion.

Structure

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

HMDB0041893
     RDKit          3D
Fenitrothion
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.6753   -1.7374   -0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.4886   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434    0.4141   -0.1904 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.7312    1.8664   -1.1132 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    0.8255    1.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911    1.9930    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2100   -0.4444   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -0.1988   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.6623   -1.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    0.8828   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    0.2123   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2670    0.4546   -0.3405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7957    0.4050    0.7842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0529    0.7440   -1.4140 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1943   -0.6552    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180   -1.3779    1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376   -0.8432    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090   -2.4836   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.9318   -0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1988   -1.7652   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640    2.1518    2.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    2.0305    1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951    2.8407    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765    1.1618   -2.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094    1.5670   -2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030   -2.0534    1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.6779    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044   -2.0112    0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489   -1.5432    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  2  0
 17  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  6 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
M  CHG  2  12   1  14  -1
M  END


  Mrv0541 09131211462D          

 17 17  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  2  0  0  0  0
 13  2  1  0  0  0  0
 14  3  1  0  0  0  0
 15  8  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041893

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3

> <INCHI_KEY>
ZNOLGFHPUIJIMJ-UHFFFAOYSA-N

> <FORMULA>
C9H12NO5PS

> <MOLECULAR_WEIGHT>
277.234

> <EXACT_MASS>
277.017379701

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.742840833728636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
3.1150119569999997

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
73.51

> <JCHEM_REFRACTIVITY>
68.23320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041893
     RDKit          3D
Fenitrothion
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.6753   -1.7374   -0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.4886   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434    0.4141   -0.1904 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.7312    1.8664   -1.1132 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    0.8255    1.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911    1.9930    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2100   -0.4444   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -0.1988   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.6623   -1.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    0.8828   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    0.2123   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2670    0.4546   -0.3405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7957    0.4050    0.7842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0529    0.7440   -1.4140 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1943   -0.6552    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180   -1.3779    1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376   -0.8432    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090   -2.4836   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.9318   -0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1988   -1.7652   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640    2.1518    2.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    2.0305    1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951    2.8407    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765    1.1618   -2.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094    1.5670   -2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030   -2.0534    1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.6779    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044   -2.0112    0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489   -1.5432    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  2  0
 17  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  6 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
M  CHG  2  12   1  14  -1
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.310  -1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -5.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.770  -1.746   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.770  -4.414   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       0.000  -3.080   0.000  0.00  0.00           P+0
HETATM   17  S   UNK     0      -1.334  -3.850   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    7    8                                                       
CONECT    7    1    6    9                                                  
CONECT    8    4    6   15                                                  
CONECT    9    5    7   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   16                                                       
CONECT   14    3   16                                                       
CONECT   15    8   16                                                       
CONECT   16   13   14   15   17                                             
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0041893
HETATM    1  C1  UNL     1       3.675  -1.737  -0.813  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.866  -0.489  -0.227  1.00  0.00           O  
HETATM    3  P1  UNL     1       2.443   0.414  -0.190  1.00  0.00           P  
HETATM    4  S1  UNL     1       2.731   1.866  -1.113  1.00  0.00           S  
HETATM    5  O2  UNL     1       2.091   0.826   1.399  1.00  0.00           O  
HETATM    6  C2  UNL     1       2.791   1.993   1.693  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.210  -0.444  -0.964  1.00  0.00           O  
HETATM    8  C3  UNL     1      -0.140  -0.199  -0.839  1.00  0.00           C  
HETATM    9  C4  UNL     1      -0.823   0.662  -1.662  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.196   0.883  -1.499  1.00  0.00           C  
HETATM   11  C6  UNL     1      -2.871   0.212  -0.484  1.00  0.00           C  
HETATM   12  N1  UNL     1      -4.267   0.455  -0.341  1.00  0.00           N1+
HETATM   13  O4  UNL     1      -4.796   0.405   0.784  1.00  0.00           O  
HETATM   14  O5  UNL     1      -5.053   0.744  -1.414  1.00  0.00           O1-
HETATM   15  C7  UNL     1      -2.194  -0.655   0.348  1.00  0.00           C  
HETATM   16  C8  UNL     1      -2.918  -1.378   1.441  1.00  0.00           C  
HETATM   17  C9  UNL     1      -0.838  -0.843   0.152  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.109  -2.484  -0.121  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.578  -1.932  -0.964  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.199  -1.765  -1.786  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.964   2.152   2.759  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.778   2.030   1.165  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.195   2.841   1.282  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.277   1.162  -2.433  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.709   1.567  -2.161  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.203  -2.053   1.943  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.293  -0.678   2.209  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.704  -2.011   0.992  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.349  -1.543   0.841  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4    5    7
CONECT    5    6
CONECT    6   21   22   23
CONECT    7    8
CONECT    8    9    9   17
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   15
CONECT   12   13   13   14
CONECT   15   16   17   17
CONECT   16   26   27   28
CONECT   17   29
END

HMDB0041893
     RDKit          3D
Fenitrothion
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.6753   -1.7374   -0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.4886   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434    0.4141   -0.1904 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.7312    1.8664   -1.1132 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    0.8255    1.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911    1.9930    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2100   -0.4444   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -0.1988   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.6623   -1.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    0.8828   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    0.2123   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2670    0.4546   -0.3405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7957    0.4050    0.7842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0529    0.7440   -1.4140 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1943   -0.6552    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180   -1.3779    1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376   -0.8432    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090   -2.4836   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.9318   -0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1988   -1.7652   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9640    2.1518    2.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    2.0305    1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951    2.8407    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765    1.1618   -2.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094    1.5670   -2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030   -2.0534    1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.6779    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044   -2.0112    0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489   -1.5432    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  2  0
 17  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  6 22  1  0
  6 23  1  0
  9 24  1  0
 10 25  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
M  CHG  2  12   1  14  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
MEP	ChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate	ChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) thiophosphate	ChEBI
O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioate	ChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioic acid	Generator
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) thiophosphoric acid	Generator
O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioic acid	Generator
Accothion	HMDB
Aceothion	HMDB
Agriya 1050	HMDB
Agrothion	HMDB
Akotion	HMDB
American cyanamid CL-47,300	HMDB
Arbogal	HMDB
Bayer S 5660	HMDB
Bis-fenitrothion	HMDB
Cekutrothion	HMDB
Cyfen	HMDB
Cytel	HMDB
Cyten	HMDB
Dicofen	HMDB
Dimethyl 3-methyl-4-nitrophenyl phosphorothionate	HMDB
Dimethyl 4-nitro-m-tolyl phosphorothionate	HMDB
Falithion	HMDB
Fenitox	HMDB
Fenitrotion	HMDB
Folithion	HMDB
Folithion ec 50	HMDB
Kotion	HMDB
Macbar	HMDB
MEP (pesticide)	HMDB
MEP (phosphorus insecticide)	HMDB
Metathio e-50	HMDB
Metathion	HMDB
Metathion e-50	HMDB
Metathione	HMDB
Metathionine	HMDB
Metathionine e-50	HMDB
Metation	HMDB
Metation e-50	HMDB
Methylnitrophos	HMDB
Mglawik F	HMDB
Nitrophos	HMDB
Novathion	HMDB
Nuvanol	HMDB
O,O-DiMe O-(3-methyl-4-nitrophenyl) thiophosphate	HMDB
O,O-Dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate	HMDB
O,O-Dimethyl O-(4-nitro-3-methylphenyl)thiophosphate	HMDB
O,O-Dimethyl O-4-nitro-m-tolyl thiophosphate	HMDB
O,O-Dimethyl-O-(3-methyl-4-nitro-phenyl)-monothiophosphate	HMDB
O,O-Dimethyl-O-(3-methyl-4-nitrofenyl)-monothiofosfaat	HMDB
O,O-Dimethyl-O-(4-nitro-5-methylphenyl)-thionophosphate	HMDB
O,O-Dimetil-O-(3-metil-4-nitro-fenil)-monotiofosfato	HMDB
O,O-Dimetil-O-(3-metil-4-nitrofenil) fosforotioato	HMDB
Oleometathion	HMDB
Oleosumifene	HMDB
Ovadofos	HMDB
Owadofos	HMDB
Owadophos	HMDB
Pennwalt C-4852	HMDB
Phenitrothion	HMDB
Sumifene	HMDB
Sumigran	HMDB
Sumithian	HMDB
Sumithion	HMDB
Sumitomo S-1102a	HMDB
Tionfos 50 le	HMDB
Verthion	HMDB
1050, Agria	HMDB
Agria 1050	HMDB
Sumithione	HMDB

Chemical Formula

C₉H₁₂NO₅PS

Average Molecular Weight

277.234

Monoisotopic Molecular Weight

277.017379701

IUPAC Name

O,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate

Traditional Name

O,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate

CAS Registry Number

122-14-5

SMILES

COP(=S)(OC)OC1=CC=C(C(C)=C1)N(=O)=O

InChI Identifier

InChI=1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3

InChI Key

ZNOLGFHPUIJIMJ-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
Nitrobenzene
Nitrotoluene
Phenoxy compound
Nitroaromatic compound
Thiophosphate triester
Toluene
Monocyclic benzene moiety
Benzenoid
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:34757 )
organic thiophosphate (CHEBI:34757 )
Organophosphorus insecticides (C14442 )
a small molecule (CPD-8975 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041893)

Source

Exogenous

Exogenous (HMDB: HMDB0041893)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0041893)

Agriculture

Pesticide

Insecticide (HMDB: HMDB0041893)
Acaricide (HMDB: HMDB0041893)

Biological role

Modulator

Inhibitor

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0041893)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0041893)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	3.4 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.038 mg/mL at 25 °C	Not Available
LogP	3.30	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	3.31	ALOGPS
logP	3.12	ChemAxon
logS	-4.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	73.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.23 m³·mol⁻¹	ChemAxon
Polarizability	24.74 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]+	162.649	31661259
DarkChem	[M-H]-	159.674	31661259
DeepCCS	[M+H]+	152.76	30932474
DeepCCS	[M-H]-	150.402	30932474
DeepCCS	[M-2H]-	183.358	30932474
DeepCCS	[M+Na]+	158.853	30932474
AllCCS	[M+H]+	154.7	32859911
AllCCS	[M+H-H2O]+	151.4	32859911
AllCCS	[M+NH4]+	157.8	32859911
AllCCS	[M+Na]+	158.6	32859911
AllCCS	[M-H]-	154.8	32859911
AllCCS	[M+Na-2H]-	154.8	32859911
AllCCS	[M+HCOO]-	155.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fenitrothion	COP(=S)(OC)OC1=CC=C(C(C)=C1)N(=O)=O	2906.9	Standard polar	33892256
Fenitrothion	COP(=S)(OC)OC1=CC=C(C(C)=C1)N(=O)=O	1910.7	Standard non polar	33892256
Fenitrothion	COP(=S)(OC)OC1=CC=C(C(C)=C1)N(=O)=O	1904.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Fenitrothion EI-B (Non-derivatized)	splash10-01tc-9540000000-a180b7cec61770691237	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Fenitrothion EI-B (Non-derivatized)	splash10-004i-1980000000-469fd8d8b5afef55db6d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Fenitrothion EI-B (Non-derivatized)	splash10-01tc-9540000000-a180b7cec61770691237	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Fenitrothion EI-B (Non-derivatized)	splash10-004i-1980000000-469fd8d8b5afef55db6d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenitrothion GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-3950000000-0b6ab147cddeb288eed5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenitrothion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-8980000000-4c5af1b2fb42bdb10504	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 10V, Positive-QTOF	splash10-004i-0090000000-2848423a70610d0dae28	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 20V, Positive-QTOF	splash10-0fk9-0090000000-d10a1515515bbdc69975	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 40V, Positive-QTOF	splash10-000x-3940000000-5cc3638b33f222c4352c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 10V, Negative-QTOF	splash10-004i-0390000000-e49f20ded24e19945287	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 20V, Negative-QTOF	splash10-00b9-0490000000-c57ad69bf50c72792ac7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 40V, Negative-QTOF	splash10-0a4l-1900000000-d97d44855ea21933b936	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 10V, Negative-QTOF	splash10-004i-0090000000-15d4b7303fe1f263e6e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 20V, Negative-QTOF	splash10-004i-0090000000-15d4b7303fe1f263e6e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 40V, Negative-QTOF	splash10-003r-9380000000-15ab04f4c83619b667be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 10V, Positive-QTOF	splash10-004i-0090000000-4047b7defcfd38181f33	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 20V, Positive-QTOF	splash10-004i-0390000000-106366d9a50461b52a49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenitrothion 40V, Positive-QTOF	splash10-00xr-8910000000-5b5ac2d7434bed2a6cd8	2021-09-23	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28941

KEGG Compound ID

C14442

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenitrothion

METLIN ID

Not Available

PubChem Compound

31200

PDB ID

Not Available

ChEBI ID

34757

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 Fenitrothion (HMDB0041893)

MOL for HMDB0041893 (Fenitrothion)

3D MOL for HMDB0041893 (Fenitrothion)

3D SDF for HMDB0041893 (Fenitrothion)

3D-SDF for HMDB0041893 (Fenitrothion)

PDB for HMDB0041893 (Fenitrothion)

3D PDB for HMDB0041893 (Fenitrothion)

SMILES for HMDB0041893 (Fenitrothion)

INCHI for HMDB0041893 (Fenitrothion)

Structure for HMDB0041893 (Fenitrothion)

3D Structure for HMDB0041893 (Fenitrothion)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra