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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:55:18 UTC

Update Date

2022-03-07 02:53:37 UTC

HMDB ID

HMDB0033209

Secondary Accession Numbers

HMDB33209

Metabolite Identification

Common Name

Fenthion

Description

Fenthion is an insecticide with low mammalian toxicity. Fenthion is used in agriculture and against mosquito larvae in tropical fresh waters.Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class. (Wikipedia ).

Structure

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

HMDB0033209
     RDKit          3D
Fenthion
 31 31  0  0  0  0  0  0  0  0999 V2000
    5.1069    0.9659   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9596    1.3444   -1.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    0.2558   -0.6520 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3445   -1.3293   -0.8761 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253    0.5430    1.0070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -0.5965    1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.5592   -1.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900    0.1385   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815   -1.1074   -1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6125   -1.5168   -0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -0.6871   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255   -1.2419    0.5340 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2925   -0.8395   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095    0.5701    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    1.5106    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848    0.9487   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0224    1.2694   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070   -0.1381   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405    1.3718    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026   -0.7855    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -0.4460    2.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080   -1.4512    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -1.7550   -2.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263   -2.5152   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0174   -0.9179   -1.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136   -1.5535   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6992    0.1720   -0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900    2.1646    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    0.9595    1.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2785    2.1786    0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    1.9291   -0.0317 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  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
M  END


  Mrv1652307282022232D          

 16 16  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.0000    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    1.2375    0.0000 S   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033209

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3

> <INCHI_KEY>
PNVJTZOFSHSLTO-UHFFFAOYSA-N

> <FORMULA>
C10H15O3PS2

> <MOLECULAR_WEIGHT>
278.328

> <EXACT_MASS>
278.020022238

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.221358266557033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
3.8032449059999998

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
73.66740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fenthion

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033209
     RDKit          3D
Fenthion
 31 31  0  0  0  0  0  0  0  0999 V2000
    5.1069    0.9659   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9596    1.3444   -1.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    0.2558   -0.6520 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3445   -1.3293   -0.8761 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253    0.5430    1.0070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -0.5965    1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.5592   -1.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900    0.1385   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815   -1.1074   -1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6125   -1.5168   -0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -0.6871   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255   -1.2419    0.5340 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2925   -0.8395   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095    0.5701    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    1.5106    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848    0.9487   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0224    1.2694   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070   -0.1381   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405    1.3718    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026   -0.7855    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -0.4460    2.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080   -1.4512    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -1.7550   -2.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263   -2.5152   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0174   -0.9179   -1.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136   -1.5535   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6992    0.1720   -0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900    2.1646    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    0.9595    1.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2785    2.1786    0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    1.9291   -0.0317 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  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
M  END

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0       5.335   0.000   0.000  0.00  0.00           P+0
HETATM    4  S   UNK     0       4.565   1.334   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0       6.105  -1.334   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335  -2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      -1.334   2.310   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    7                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0033209
HETATM    1  C1  UNL     1       5.107   0.966  -0.432  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.960   1.344  -1.104  1.00  0.00           O  
HETATM    3  P1  UNL     1       2.726   0.256  -0.652  1.00  0.00           P  
HETATM    4  S1  UNL     1       3.344  -1.329  -0.876  1.00  0.00           S  
HETATM    5  O2  UNL     1       2.425   0.543   1.007  1.00  0.00           O  
HETATM    6  C2  UNL     1       2.720  -0.597   1.748  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.328   0.559  -1.565  1.00  0.00           O  
HETATM    8  C3  UNL     1       0.090   0.139  -1.069  1.00  0.00           C  
HETATM    9  C4  UNL     1      -0.382  -1.107  -1.376  1.00  0.00           C  
HETATM   10  C5  UNL     1      -1.613  -1.517  -0.879  1.00  0.00           C  
HETATM   11  C6  UNL     1      -2.369  -0.687  -0.078  1.00  0.00           C  
HETATM   12  S2  UNL     1      -3.926  -1.242   0.534  1.00  0.00           S  
HETATM   13  C7  UNL     1      -5.293  -0.839  -0.582  1.00  0.00           C  
HETATM   14  C8  UNL     1      -1.909   0.570   0.241  1.00  0.00           C  
HETATM   15  C9  UNL     1      -2.693   1.511   1.108  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.685   0.949  -0.267  1.00  0.00           C  
HETATM   17  H1  UNL     1       6.022   1.269  -0.997  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.107  -0.138  -0.353  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.141   1.372   0.613  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.803  -0.786   1.805  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.285  -0.446   2.757  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.208  -1.451   1.244  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.227  -1.755  -2.011  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.926  -2.515  -1.161  1.00  0.00           H  
HETATM   25  H9  UNL     1      -5.017  -0.918  -1.638  1.00  0.00           H  
HETATM   26  H10 UNL     1      -6.114  -1.553  -0.373  1.00  0.00           H  
HETATM   27  H11 UNL     1      -5.699   0.172  -0.406  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.990   2.165   1.689  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.297   0.959   1.860  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.279   2.179   0.467  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.302   1.929  -0.032  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4    5    7
CONECT    5    6
CONECT    6   20   21   22
CONECT    7    8
CONECT    8    9    9   16
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   14
CONECT   12   13
CONECT   13   25   26   27
CONECT   14   15   16   16
CONECT   15   28   29   30
CONECT   16   31
END

HMDB0033209
     RDKit          3D
Fenthion
 31 31  0  0  0  0  0  0  0  0999 V2000
    5.1069    0.9659   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9596    1.3444   -1.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    0.2558   -0.6520 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3445   -1.3293   -0.8761 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253    0.5430    1.0070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -0.5965    1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.5592   -1.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900    0.1385   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815   -1.1074   -1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6125   -1.5168   -0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -0.6871   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255   -1.2419    0.5340 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2925   -0.8395   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095    0.5701    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    1.5106    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848    0.9487   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0224    1.2694   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070   -0.1381   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405    1.3718    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026   -0.7855    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -0.4460    2.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080   -1.4512    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -1.7550   -2.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263   -2.5152   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0174   -0.9179   -1.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136   -1.5535   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6992    0.1720   -0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900    2.1646    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    0.9595    1.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2785    2.1786    0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    1.9291   -0.0317 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  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methylmercapto-3-methylphenyl dimethyl thiophosphate	ChEBI
Mercaptophos	ChEBI
MPP	ChEBI
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioate	ChEBI
O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioate	ChEBI
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphate	ChEBI
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphate	ChEBI
Phosphorothioic acid, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester	ChEBI
Tiguvon	Kegg
4-Methylmercapto-3-methylphenyl dimethyl thiophosphoric acid	Generator
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioic acid	Generator
O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioic acid	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphoric acid	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thiophosphate	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thiophosphoric acid	Generator
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphoric acid	Generator
Phosphorothioate, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester	Generator
Bayer 29493	HMDB
Baytex	HMDB, MeSH
Dimethyl (3-methyl-4-(methylthio)phenyl) phosphorothionate	HMDB
Dimethyl methylthiotolyl phosphorothioate	HMDB
Dimethyl O-(3-methyl-4-(methylthio)phenyl) thiophosphate	HMDB
Dimethyl O-(4-(methylthio)-m-tolyl) phosphorothioate	HMDB
DMTP	HMDB
ent 25540	HMDB
Entex	HMDB
Fenthione	HMDB
Figuron	HMDB
Lebaycid	HMDB, MeSH
Lebayeid	HMDB
Mosquitocide 700	HMDB
MPP (Pesticide)	HMDB
O,O-Dimethyl O-(4-methylthio-3-methylphenyl) thiophosphate	HMDB
O,O-Dimethyl O-[(3-methyl-4-methylthio)phenyl] phosphorothioate, 9ci	HMDB
O,O-Dimethyl-O-[4-(methylthio)-m-tolyl] phosphorothioate	HMDB
Phenthion	HMDB
Queletox	HMDB
Spotton	HMDB
Talodex	HMDB

Chemical Formula

C₁₀H₁₅O₃PS₂

Average Molecular Weight

278.328

Monoisotopic Molecular Weight

278.020022238

IUPAC Name

O,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate

Traditional Name

fenthion

CAS Registry Number

55-38-9

SMILES

COP(=S)(OC)OC1=CC=C(SC)C(C)=C1

InChI Identifier

InChI=1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3

InChI Key

PNVJTZOFSHSLTO-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
Aryl thioether
Thiophosphate triester
Thiophenol ether
Toluene
Alkylarylthioether
Monocyclic benzene moiety
Benzenoid
Thioether
Sulfenyl compound
Organosulfur compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organic thiophosphate (CHEBI:34761 )
Organophosphorus insecticides (C14420 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0033209)
Hypotension (HMDB: HMDB0033209)

Nervous system disorder

Headache (HMDB: HMDB0033209)
Tremor (HMDB: HMDB0033209)

Central nervous system disorder

Psychiatric disorder

Depression (HMDB: HMDB0033209)
Anxiety (HMDB: HMDB0033209)

Peripheral nervous system disorder

Sympathetic nervous system disorder

Visual system disorder

Blurred vision (HMDB: HMDB0033209)

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0033209)
Nausea (HMDB: HMDB0033209)

Disposition

Biological location

Cell membrane (HMDB: HMDB0033209)

Cellular substructure

Membrane (HMDB: HMDB0033209)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033209)

Source

Exogenous

Food

Food (HMDB: HMDB0033209)

Process

Not Available

Role

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	7.5 °C	Not Available
Boiling Point	251.00 to 253.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0075 mg/mL at 20 °C	Not Available
LogP	4.09	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	3.93	ALOGPS
logP	3.8	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.67 m³·mol⁻¹	ChemAxon
Polarizability	27.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.61	31661259
DarkChem	[M-H]-	159.933	31661259
DeepCCS	[M+H]+	156.319	30932474
DeepCCS	[M-H]-	153.961	30932474
DeepCCS	[M-2H]-	187.051	30932474
DeepCCS	[M+Na]+	162.412	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	157.9	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fenthion	COP(=S)(OC)OC1=CC=C(SC)C(C)=C1	2826.4	Standard polar	33892256
Fenthion	COP(=S)(OC)OC1=CC=C(SC)C(C)=C1	1961.7	Standard non polar	33892256
Fenthion	COP(=S)(OC)OC1=CC=C(SC)C(C)=C1	1979.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Fenthion EI-B (Non-derivatized)	splash10-00os-4930000000-d917f6fe7c279d0326ef	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Fenthion EI-B (Non-derivatized)	splash10-00os-4930000000-d917f6fe7c279d0326ef	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenthion GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ik9-1970000000-38f4eb65b0f142b27c42	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenthion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenthion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-7970000000-bc43a51c3e0e0f2a8537	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOF	splash10-004i-0090000000-cfc6cc7271f15039d91e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOF	splash10-014j-0940000000-4c4cfaec8b9d90f02220	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOF	splash10-0gb9-0910000000-30762456be8c99676446	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOF	splash10-0gi0-0900000000-fc2e0d1f56a644607b35	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOF	splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion LC-ESI-QFT , positive-QTOF	splash10-001i-0290000000-9da11dc2725fc111b8c4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 20V, Positive-QTOF	splash10-014j-0940000000-199b003861522f4b62e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 30V, Positive-QTOF	splash10-0gb9-0910000000-14a50b7ed49de35229bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 40V, Positive-QTOF	splash10-0gi0-0900000000-fc2e0d1f56a644607b35	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 50V, Positive-QTOF	splash10-0g4i-0900000000-daf8e3082dcd599a9ef6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 50V, Positive-QTOF	splash10-0g4i-0900000000-677923a06bbdab3e4faa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 30V, Positive-QTOF	splash10-0v4i-0910000000-d74e5478dcae4fb77f71	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 40V, Positive-QTOF	splash10-0g4i-0900000000-c7ed3dac5d73de1abfe2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 35V, Positive-QTOF	splash10-001i-0290000000-c4282f269db3a3c433b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 20V, Positive-QTOF	splash10-014j-0940000000-49b2bd577f2239e1eeed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 10V, Positive-QTOF	splash10-004i-0090000000-03e61a06874c5e65189c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenthion 50V, Positive-QTOF	splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 10V, Positive-QTOF	splash10-004i-0190000000-74fefa9007324dd9847e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 20V, Positive-QTOF	splash10-002r-1970000000-6492e585fe189b3d02a0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 40V, Positive-QTOF	splash10-01pc-9880000000-8949ee35385684bf0416	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 10V, Negative-QTOF	splash10-005c-0290000000-b55d858a805aaba2db82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 20V, Negative-QTOF	splash10-003r-0290000000-6e342595466184c4595b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 40V, Negative-QTOF	splash10-0a4l-2900000000-eb2a165616e3235fce1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 10V, Positive-QTOF	splash10-004i-0190000000-953bec3de0724b9038a4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenthion 20V, Positive-QTOF	splash10-004u-4790000000-c6f5d3f2adc0c2093b0b	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

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

DB11412

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011222

KNApSAcK ID

Not Available

Chemspider ID

3229

KEGG Compound ID

C14420

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenthion

METLIN ID

Not Available

PubChem Compound

3346

PDB ID

Not Available

ChEBI ID

34761

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1045951

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Fenthion (HMDB0033209)

MOL for HMDB0033209 (Fenthion)

3D MOL for HMDB0033209 (Fenthion)

3D SDF for HMDB0033209 (Fenthion)

3D-SDF for HMDB0033209 (Fenthion)

PDB for HMDB0033209 (Fenthion)

3D PDB for HMDB0033209 (Fenthion)

SMILES for HMDB0033209 (Fenthion)

INCHI for HMDB0033209 (Fenthion)

Structure for HMDB0033209 (Fenthion)

3D Structure for HMDB0033209 (Fenthion)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra