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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:07:26 UTC

Update Date

2021-09-26 23:12:22 UTC

HMDB ID

HMDB0256600

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pirimiphos-methyl

Description

Pirimiphos-methyl 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 a small amount of articles have been published on Pirimiphos-methyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pirimiphos-methyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pirimiphos-methyl 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

HMDB0256600
     RDKit          3D
Pirimiphos-methyl
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.8160    0.7629   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9592   -0.4589   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -0.4426    0.2208 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172   -0.5192    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    0.6921    2.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -0.3500   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.3063   -1.5719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -0.2110   -2.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315   -0.1668   -3.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493   -0.1561   -1.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -0.1975    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215   -0.1425    1.1511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -0.0190    0.7224 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.0007   -1.3150   -0.2662 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840    0.0314    2.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -1.2341    2.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384    1.4620   -0.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9185    1.5817   -0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -0.2929    0.5976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2630    1.6785   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7091    0.5639   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2279    0.8768   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6039   -1.3348   -0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6227   -0.7208   -1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -0.7056    2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624   -1.3951    1.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8737    0.6999    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429    0.6814    3.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3711    1.6454    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5549    0.1878   -4.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.3666   -3.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710   -1.2427   -3.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -0.0797   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1665   -1.2467    3.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8859   -1.9094    2.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -1.5658    1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827    1.1726   -1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6368    0.9545   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2312    2.6551   -0.6277 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  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 11 19  2  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
M  END

 
  Mrv0541 09271209582D          
 
 19 19  0  0  0  0            999 V2000
    7.4664   -8.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4664   -9.7765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1809  -10.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8954   -9.7765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8954   -8.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1809   -8.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6209   -8.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3311   -8.9424    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.0456   -9.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7436   -8.2279    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.9104   -9.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7633   -8.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4713  -10.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7519   -8.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1809  -11.0139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565  -11.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8854  -11.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5851  -11.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7470  -11.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
  1 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256600

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)C1=NC(OP(=S)(OC)OC)=CC(C)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3

> <INCHI_KEY>
QHOQHJPRIBSPCY-UHFFFAOYSA-N

> <FORMULA>
C11H20N3O3PS

> <MOLECULAR_WEIGHT>
305.334

> <EXACT_MASS>
305.096298723

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.710138228587727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O-2-(diethylamino)-6-methylpyrimidin-4-yl O,O-dimethyl phosphorothioate

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
2.964369507333334

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.086245122297329

> <JCHEM_POLAR_SURFACE_AREA>
56.710000000000015

> <JCHEM_REFRACTIVITY>
81.3084

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-2-(diethylamino)-6-methylpyrimidin-4-yl O,O-dimethyl phosphorothioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256600
     RDKit          3D
Pirimiphos-methyl
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.8160    0.7629   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9592   -0.4589   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -0.4426    0.2208 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172   -0.5192    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    0.6921    2.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -0.3500   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.3063   -1.5719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -0.2110   -2.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315   -0.1668   -3.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493   -0.1561   -1.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -0.1975    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215   -0.1425    1.1511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -0.0190    0.7224 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.0007   -1.3150   -0.2662 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840    0.0314    2.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -1.2341    2.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384    1.4620   -0.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9185    1.5817   -0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -0.2929    0.5976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2630    1.6785   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7091    0.5639   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2279    0.8768   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6039   -1.3348   -0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6227   -0.7208   -1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -0.7056    2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624   -1.3951    1.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8737    0.6999    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429    0.6814    3.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3711    1.6454    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5549    0.1878   -4.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.3666   -3.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710   -1.2427   -3.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -0.0797   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1665   -1.2467    3.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8859   -1.9094    2.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -1.5658    1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827    1.1726   -1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6368    0.9545   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2312    2.6551   -0.6277 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  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 11 19  2  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 27-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-12         0                                  
HETATM    1  C   UNK     0      13.937 -16.709   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      13.937 -18.249   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      15.271 -19.019   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      16.605 -18.249   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      16.605 -16.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.271 -15.939   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      17.959 -15.927   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      19.285 -16.693   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      20.618 -17.463   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0      20.055 -15.359   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0      18.499 -18.208   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.958 -16.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.546 -19.543   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.604 -15.939   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      15.271 -20.559   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      13.919 -21.340   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.586 -21.319   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.892 -20.565   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.594 -20.576   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8   12                                                       
CONECT   10    8                                                            
CONECT   11    8   13                                                       
CONECT   12    9                                                            
CONECT   13   11                                                            
CONECT   14    1                                                            
CONECT   15    3   16   17                                                  
CONECT   16   15   19                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0256600
HETATM    1  C1  UNL     1      -4.816   0.763  -0.681  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.959  -0.459  -0.709  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.860  -0.443   0.221  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.117  -0.519   1.634  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.787   0.692   2.215  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.527  -0.350  -0.257  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.235  -0.306  -1.572  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.025  -0.211  -2.036  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.332  -0.167  -3.497  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.049  -0.156  -1.126  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.796  -0.198   0.213  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.821  -0.143   1.151  1.00  0.00           O  
HETATM   13  P1  UNL     1       3.452  -0.019   0.722  1.00  0.00           P  
HETATM   14  S1  UNL     1       4.001  -1.315  -0.266  1.00  0.00           S  
HETATM   15  O2  UNL     1       4.384   0.031   2.134  1.00  0.00           O  
HETATM   16  C10 UNL     1       4.779  -1.234   2.510  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.638   1.462  -0.116  1.00  0.00           O  
HETATM   18  C11 UNL     1       4.918   1.582  -0.625  1.00  0.00           C  
HETATM   19  N3  UNL     1      -0.482  -0.293   0.598  1.00  0.00           N  
HETATM   20  H1  UNL     1      -4.263   1.679  -0.386  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.709   0.564  -0.058  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.228   0.877  -1.725  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.604  -1.335  -0.416  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.623  -0.721  -1.746  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.162  -0.706   2.212  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.762  -1.395   1.897  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.874   0.700   2.174  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.543   0.681   3.321  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.371   1.645   1.830  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.555   0.188  -4.042  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.255   0.367  -3.724  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.471  -1.243  -3.794  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.074  -0.080  -1.499  1.00  0.00           H  
HETATM   34  H15 UNL     1       5.167  -1.247   3.531  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.886  -1.909   2.458  1.00  0.00           H  
HETATM   36  H17 UNL     1       5.578  -1.566   1.796  1.00  0.00           H  
HETATM   37  H18 UNL     1       4.983   1.173  -1.674  1.00  0.00           H  
HETATM   38  H19 UNL     1       5.637   0.954  -0.039  1.00  0.00           H  
HETATM   39  H20 UNL     1       5.231   2.655  -0.628  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4    6
CONECT    4    5   25   26
CONECT    5   27   28   29
CONECT    6    7    7   19
CONECT    7    8
CONECT    8    9   10   10
CONECT    9   30   31   32
CONECT   10   11   33
CONECT   11   12   19   19
CONECT   12   13
CONECT   13   14   14   15   17
CONECT   15   16
CONECT   16   34   35   36
CONECT   17   18
CONECT   18   37   38   39
END

HMDB0256600
     RDKit          3D
Pirimiphos-methyl
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.8160    0.7629   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9592   -0.4589   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -0.4426    0.2208 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172   -0.5192    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    0.6921    2.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -0.3500   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.3063   -1.5719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -0.2110   -2.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315   -0.1668   -3.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493   -0.1561   -1.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -0.1975    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215   -0.1425    1.1511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -0.0190    0.7224 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.0007   -1.3150   -0.2662 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840    0.0314    2.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -1.2341    2.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384    1.4620   -0.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9185    1.5817   -0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -0.2929    0.5976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2630    1.6785   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7091    0.5639   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2279    0.8768   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6039   -1.3348   -0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6227   -0.7208   -1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -0.7056    2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624   -1.3951    1.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8737    0.6999    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429    0.6814    3.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3711    1.6454    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5549    0.1878   -4.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.3666   -3.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710   -1.2427   -3.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -0.0797   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1665   -1.2467    3.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8859   -1.9094    2.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -1.5658    1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827    1.1726   -1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6368    0.9545   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2312    2.6551   -0.6277 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  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 11 19  2  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
O-[2-(Diethylamino)-6-methylpyrimidin-4-yl] O,O-dimethyl thiophosphate	ChEBI
Pirimifosmethyl	ChEBI
Pirimiphos methyl	ChEBI
Pirimiphosmethyl	ChEBI
Pyrimiphos methyl	ChEBI
O-[2-(Diethylamino)-6-methylpyrimidin-4-yl] O,O-dimethyl thiophosphoric acid	Generator
Piritione	MeSH
O-(2-(diethylamino)-6-Methyl-4-pyrimidinyl) O,O- dimethylphosphorothioate lic	MeSH
Actellic	MeSH
Aktel	MeSH

Chemical Formula

C₁₁H₂₀N₃O₃PS

Average Molecular Weight

305.334

Monoisotopic Molecular Weight

305.096298723

IUPAC Name

O-2-(diethylamino)-6-methylpyrimidin-4-yl O,O-dimethyl phosphorothioate

Traditional Name

O-2-(diethylamino)-6-methylpyrimidin-4-yl O,O-dimethyl phosphorothioate

CAS Registry Number

Not Available

SMILES

CCN(CC)C1=NC(OP(=S)(OC)OC)=CC(C)=N1

InChI Identifier

InChI=1S/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3

InChI Key

QHOQHJPRIBSPCY-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
Dialkylarylamine
Thiophosphate triester
Aminopyrimidine
Pyrimidine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyrimidine (CHEBI:38843 )
organic thiophosphate (CHEBI:38843 )
Organophosphorus insecticides (C18403 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0256600)
actin filament (HMDB: HMDB0256600)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Aflatoxin Biosynthesis (HMDB: HMDB0256600)

Role

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	3.91	ALOGPS
logP	2.96	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	5.09	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.71 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.31 m³·mol⁻¹	ChemAxon
Polarizability	30.71 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
DeepCCS	[M+H]+	166.6	30932474
DeepCCS	[M-H]-	164.242	30932474
DeepCCS	[M-2H]-	197.128	30932474
DeepCCS	[M+Na]+	172.693	30932474
AllCCS	[M+H]+	166.0	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.5	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	168.2	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pirimiphos-methyl	CCN(CC)C1=NC(OP(=S)(OC)OC)=CC(C)=N1	2635.3	Standard polar	33892256
Pirimiphos-methyl	CCN(CC)C1=NC(OP(=S)(OC)OC)=CC(C)=N1	1982.7	Standard non polar	33892256
Pirimiphos-methyl	CCN(CC)C1=NC(OP(=S)(OC)OC)=CC(C)=N1	1934.4	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 - Pirimiphos-methyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-1490000000-30fac2b7c9208b9d4e6e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirimiphos-methyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004l-9671000000-db466e16c69b326f2d7b	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 - Pirimiphos-methyl 35V, Positive-QTOF	splash10-0200-0790000000-784b40098216be79a581	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 40V, Positive-QTOF	splash10-03ki-0900000000-895cdb27adc01302a330	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 30V, Positive-QTOF	splash10-03di-0911000000-ba5b0672e4bab27ca388	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 55V, Positive-QTOF	splash10-0200-0790000000-952c08c209a5666e2f14	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 80V, Positive-QTOF	splash10-0a4i-1900000000-4e8a11388a8353420139	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 10V, Positive-QTOF	splash10-0a4i-0009000000-3966cebde88daac933fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 20V, Positive-QTOF	splash10-0a4i-0209000000-6dbf3dcfe0e322198dab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 55V, Positive-QTOF	splash10-0bt9-1900000000-51e7080196d96c82db04	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 35V, Positive-QTOF	splash10-0gb9-0900000000-7101d86decc6c087bc16	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 50V, Positive-QTOF	splash10-0fkc-0900000000-396ee6ab0c0839693cff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 35V, Positive-QTOF	splash10-0a4i-1719000000-3aed70af03fb848971a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirimiphos-methyl 50V, Positive-QTOF	splash10-0fkc-0900000000-ffa782226105d26603d5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirimiphos-methyl 10V, Positive-QTOF	splash10-0a4i-0359000000-416ae91c212df63bf10b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirimiphos-methyl 20V, Positive-QTOF	splash10-03di-0692000000-54185c472d72dd012c95	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirimiphos-methyl 40V, Positive-QTOF	splash10-03dr-7940000000-945d6b4e6fff3fd05f1b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirimiphos-methyl 10V, Negative-QTOF	splash10-0udi-0569000000-3f964fdb65d2baa50628	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirimiphos-methyl 20V, Negative-QTOF	splash10-0btc-0691000000-b6717f4381802607d73c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirimiphos-methyl 40V, Negative-QTOF	splash10-052f-1920000000-9714a9ea8031c043cca8	2016-08-03	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

31773

KEGG Compound ID

C18403

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pirimiphos-methyl

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

38843

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1313461

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 Pirimiphos-methyl (HMDB0256600)

MOL for HMDB0256600 (Pirimiphos-methyl)

3D MOL for HMDB0256600 (Pirimiphos-methyl)

3D SDF for HMDB0256600 (Pirimiphos-methyl)

3D-SDF for HMDB0256600 (Pirimiphos-methyl)

PDB for HMDB0256600 (Pirimiphos-methyl)

3D PDB for HMDB0256600 (Pirimiphos-methyl)

SMILES for HMDB0256600 (Pirimiphos-methyl)

INCHI for HMDB0256600 (Pirimiphos-methyl)

Structure for HMDB0256600 (Pirimiphos-methyl)

3D Structure for HMDB0256600 (Pirimiphos-methyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra