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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:26 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031783

Secondary Accession Numbers

HMDB31783

Metabolite Identification

Common Name

Etrimfos

Description

Etrimfos, also known as satisfar or ekamet, belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom. Based on a literature review very few articles have been published on Etrimfos.

Structure

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

HMDB0031783
     RDKit          3D
Etrimfos
 35 35  0  0  0  0  0  0  0  0999 V2000
   -3.7240    2.0848    0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    2.4243   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597    2.1000   -0.6175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834    0.8195   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    0.6024   -0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864   -0.6522   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -0.9677   -0.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2016    0.0894   -0.4592 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.2951    0.5543   -2.1387 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954    1.5049    0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019    1.4362    1.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -0.7216   -0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3365   -1.1108   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -1.6540    0.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -1.4761    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -2.6592    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9351   -2.3215    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -0.2373   -0.1684 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5970    1.4193    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964    1.4998    1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    2.9681    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527    1.9301   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433    3.5174   -0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789    1.4007   -0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    1.8595    2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    2.0788    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    0.3824    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8859   -1.9751   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.2396   -1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3723   -1.3239   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2243   -3.0036    1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969   -3.4533   -0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -3.2696    0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2136   -1.6161   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2421   -1.9904    1.3022 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END


  Mrv0541 05061306072D          

 18 18  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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.9520    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    2.4750    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
    0.7145    1.2375    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
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031783

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC1=CC(OP(=S)(OC)OC)=NC(CC)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N2O4PS/c1-5-8-11-9(15-6-2)7-10(12-8)16-17(18,13-3)14-4/h7H,5-6H2,1-4H3

> <INCHI_KEY>
FGIWFCGDPUIBEZ-UHFFFAOYSA-N

> <FORMULA>
C10H17N2O4PS

> <MOLECULAR_WEIGHT>
292.292

> <EXACT_MASS>
292.064664244

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.384012390706946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O-6-ethoxy-2-ethylpyrimidin-4-yl O,O-dimethyl phosphorothioate

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
3.535178835999999

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.964794319559715

> <JCHEM_POLAR_SURFACE_AREA>
62.70000000000002

> <JCHEM_REFRACTIVITY>
73.6217

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-6-ethoxy-2-ethylpyrimidin-4-yl O,O-dimethyl phosphorothioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031783
     RDKit          3D
Etrimfos
 35 35  0  0  0  0  0  0  0  0999 V2000
   -3.7240    2.0848    0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    2.4243   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597    2.1000   -0.6175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834    0.8195   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    0.6024   -0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864   -0.6522   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -0.9677   -0.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2016    0.0894   -0.4592 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.2951    0.5543   -2.1387 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954    1.5049    0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019    1.4362    1.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -0.7216   -0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3365   -1.1108   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -1.6540    0.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -1.4761    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -2.6592    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9351   -2.3215    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -0.2373   -0.1684 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5970    1.4193    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964    1.4998    1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    2.9681    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527    1.9301   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433    3.5174   -0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789    1.4007   -0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    1.8595    2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    2.0788    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    0.3824    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8859   -1.9751   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.2396   -1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3723   -1.3239   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2243   -3.0036    1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969   -3.4533   -0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -3.2696    0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2136   -1.6161   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2421   -1.9904    1.3022 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.691  -3.644   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.311  -3.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       2.461  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.541  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       4.001  -2.310   0.000  0.00  0.00           P+0
HETATM   18  S   UNK     0       4.001  -3.850   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    1    8                                                       
CONECT    6    2   15                                                       
CONECT    7    9   10                                                       
CONECT    8    5   11   12                                                  
CONECT    9    7   11   15                                                  
CONECT   10    7   12   16                                                  
CONECT   11    8    9                                                       
CONECT   12    8   10                                                       
CONECT   13    3   17                                                       
CONECT   14    4   17                                                       
CONECT   15    6    9                                                       
CONECT   16   10   17                                                       
CONECT   17   13   14   16   18                                             
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0031783
HETATM    1  C1  UNL     1      -3.724   2.085   0.722  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.133   2.424  -0.618  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.760   2.100  -0.618  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.283   0.819  -0.400  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.079   0.602  -0.419  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.586  -0.652  -0.208  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.922  -0.968  -0.207  1.00  0.00           O  
HETATM    8  P1  UNL     1       3.202   0.089  -0.459  1.00  0.00           P  
HETATM    9  S1  UNL     1       3.295   0.554  -2.139  1.00  0.00           S  
HETATM   10  O3  UNL     1       3.095   1.505   0.451  1.00  0.00           O  
HETATM   11  C6  UNL     1       4.002   1.436   1.517  1.00  0.00           C  
HETATM   12  O4  UNL     1       4.643  -0.722  -0.043  1.00  0.00           O  
HETATM   13  C7  UNL     1       5.337  -1.111  -1.199  1.00  0.00           C  
HETATM   14  N1  UNL     1      -0.294  -1.654   0.017  1.00  0.00           N  
HETATM   15  C8  UNL     1      -1.616  -1.476   0.041  1.00  0.00           C  
HETATM   16  C9  UNL     1      -2.475  -2.659   0.298  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.935  -2.322   0.299  1.00  0.00           C  
HETATM   18  N2  UNL     1      -2.094  -0.237  -0.168  1.00  0.00           N  
HETATM   19  H1  UNL     1      -4.597   1.419   0.560  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.996   1.500   1.339  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.022   2.968   1.305  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.653   1.930  -1.467  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.243   3.517  -0.766  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.779   1.401  -0.598  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.503   1.860   2.421  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.887   2.079   1.335  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.325   0.382   1.694  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.886  -1.975  -1.695  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.276  -0.240  -1.905  1.00  0.00           H  
HETATM   30  H12 UNL     1       6.372  -1.324  -0.899  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.224  -3.004   1.343  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.197  -3.453  -0.399  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.487  -3.270   0.074  1.00  0.00           H  
HETATM   34  H16 UNL     1      -4.214  -1.616  -0.511  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.242  -1.990   1.302  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4
CONECT    4    5    5   18
CONECT    5    6   24
CONECT    6    7   14   14
CONECT    7    8
CONECT    8    9    9   10   12
CONECT   10   11
CONECT   11   25   26   27
CONECT   12   13
CONECT   13   28   29   30
CONECT   14   15
CONECT   15   16   18   18
CONECT   16   17   31   32
CONECT   17   33   34   35
END

HMDB0031783
     RDKit          3D
Etrimfos
 35 35  0  0  0  0  0  0  0  0999 V2000
   -3.7240    2.0848    0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    2.4243   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597    2.1000   -0.6175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834    0.8195   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    0.6024   -0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864   -0.6522   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -0.9677   -0.2071 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2016    0.0894   -0.4592 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.2951    0.5543   -2.1387 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954    1.5049    0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019    1.4362    1.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -0.7216   -0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3365   -1.1108   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -1.6540    0.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -1.4761    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -2.6592    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9351   -2.3215    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -0.2373   -0.1684 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5970    1.4193    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964    1.4998    1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    2.9681    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527    1.9301   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433    3.5174   -0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789    1.4007   -0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    1.8595    2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    2.0788    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    0.3824    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8859   -1.9751   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.2396   -1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3723   -1.3239   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2243   -3.0036    1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969   -3.4533   -0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -3.2696    0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2136   -1.6161   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2421   -1.9904    1.3022 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dimethyl-O-(2-ethyl-4-ethoxy-pyrimidinyl-6)-thionophosphate	HMDB
Ekamet	HMDB
Ekamet g	HMDB
Ekamet ulv	HMDB
Etrimphos	HMDB
O-(6-Ethoxy-2-ethyl-4-pyrimidinyl) O,O-dimethyl phosphorothioate, 9ci	HMDB
Satisfar	HMDB
Satisfar DP-2	HMDB
Satisfar LS 3	HMDB
Satisfar LS 5	HMDB
SAN 197	HMDB

Chemical Formula

C₁₀H₁₇N₂O₄PS

Average Molecular Weight

292.292

Monoisotopic Molecular Weight

292.064664244

IUPAC Name

O-6-ethoxy-2-ethylpyrimidin-4-yl O,O-dimethyl phosphorothioate

Traditional Name

O-6-ethoxy-2-ethylpyrimidin-4-yl O,O-dimethyl phosphorothioate

CAS Registry Number

38260-54-7

SMILES

CCOC1=CC(OP(=S)(OC)OC)=NC(CC)=N1

InChI Identifier

InChI=1S/C10H17N2O4PS/c1-5-8-11-9(15-6-2)7-10(12-8)16-17(18,13-3)14-4/h7H,5-6H2,1-4H3

InChI Key

FGIWFCGDPUIBEZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Pyrimidinyl phosphorothioates

Alternative Parents

Substituents

Pyrimidinyl phosphorothioate
Thiophosphate triester
Alkyl aryl ether
Pyrimidine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic thiophosphate (CHEBI:82124 )
Organophosphorus insecticides (C18985 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031783)
Cell membrane (HMDB: HMDB0031783)

Source

Endogenous

Endogenous (HMDB: HMDB0031783)

Exogenous

Food

Food (HMDB: HMDB0031783)

Exogenous (HMDB: HMDB0031783)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-3.35 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.04 mg/mL at 23 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	3.39	ALOGPS
logP	3.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	2.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	62.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	73.62 m³·mol⁻¹	ChemAxon
Polarizability	28.38 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]+	166.746	31661259
DarkChem	[M-H]-	165.172	31661259
DeepCCS	[M+H]+	160.68	30932474
DeepCCS	[M-H]-	158.322	30932474
DeepCCS	[M-2H]-	191.208	30932474
DeepCCS	[M+Na]+	166.773	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	159.5	32859911
AllCCS	[M+NH4]+	165.3	32859911
AllCCS	[M+Na]+	166.1	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	162.4	32859911
AllCCS	[M+HCOO]-	163.0	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.	6.41 minutes	32390414
Predicted by Siyang on May 30, 2022	18.9872 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2576.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	651.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	242.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	410.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	779.9 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	947.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1531.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	547.5 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	1604.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	541.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	488.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	531.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	609.6 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	22.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etrimfos	CCOC1=CC(OP(=S)(OC)OC)=NC(CC)=N1	2547.9	Standard polar	33892256
Etrimfos	CCOC1=CC(OP(=S)(OC)OC)=NC(CC)=N1	1793.0	Standard non polar	33892256
Etrimfos	CCOC1=CC(OP(=S)(OC)OC)=NC(CC)=N1	1871.6	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 - Etrimfos GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-1290000000-158b70fc264d9991adef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etrimfos 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 - Etrimfos 10V, Positive-QTOF	splash10-0006-0290000000-5d393708e6ed3fd83822	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 20V, Positive-QTOF	splash10-0ufv-1590000000-01ecdfc16429c18308ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 40V, Positive-QTOF	splash10-05gi-9410000000-3a6fc9fdbcf545147ea6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 10V, Negative-QTOF	splash10-0006-0390000000-a3ec613faeb2a0d311ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 20V, Negative-QTOF	splash10-0k97-9680000000-3fd8d55bb9d42d7cedbc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 40V, Negative-QTOF	splash10-0006-6910000000-7d5f07aa462db3dc2d0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 10V, Negative-QTOF	splash10-0006-0290000000-5f3ed721276bd94ad4b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 20V, Negative-QTOF	splash10-052f-0900000000-347581aecff76e9eaff7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 40V, Negative-QTOF	splash10-0a4r-0900000000-81215fd8f26d47deb024	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 10V, Positive-QTOF	splash10-0006-0090000000-14e98e8350cacbb45624	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 20V, Positive-QTOF	splash10-0006-0490000000-672e4e663a3dd4785c4a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etrimfos 40V, Positive-QTOF	splash10-022c-3930000000-32a04995f2c22a8c7290	2021-09-22	Wishart Lab	View Spectrum

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008456

KNApSAcK ID

Not Available

Chemspider ID

34830

KEGG Compound ID

C18985

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

37995

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Etrimfos (HMDB0031783)

MOL for HMDB0031783 (Etrimfos)

3D MOL for HMDB0031783 (Etrimfos)

3D SDF for HMDB0031783 (Etrimfos)

3D-SDF for HMDB0031783 (Etrimfos)

PDB for HMDB0031783 (Etrimfos)

3D PDB for HMDB0031783 (Etrimfos)

SMILES for HMDB0031783 (Etrimfos)

INCHI for HMDB0031783 (Etrimfos)

Structure for HMDB0031783 (Etrimfos)

3D Structure for HMDB0031783 (Etrimfos)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra