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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:30:02 UTC

Update Date

2021-09-26 23:15:54 UTC

HMDB ID

HMDB0258766

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tebupirimfos

Description

Tebupirimfos, also known as phostebupirim, 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 Tebupirimfos. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tebupirimfos is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tebupirimfos 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

HMDB0258766
     RDKit          3D
Tebupirimfos
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.6020    3.2164   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946    2.3169   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9972    1.0097   -0.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428   -0.1001    0.4715 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0850    0.6568    1.7683 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903   -0.6820   -0.7243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.4692   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    0.6715   -1.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    0.8140   -0.8426 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0964   -0.1077   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5472    0.1124    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2432   -1.2322   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7285    0.5634    1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0302    1.1419   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -1.2155    0.3029 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -1.4254    0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -1.3863    1.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139   -1.5974    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1757   -1.1739    0.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0049   -2.9983   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6004    4.2427   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3362    3.2165   -1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    2.7651   -0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    2.5518    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975    2.5303   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    1.4244   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962   -2.0308   -0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -1.1202   -1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443   -1.4512    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3715   -0.3123    2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7831    0.7893    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0673    1.4395    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0444    1.5429   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000    1.9964   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    0.7211   -1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844   -2.3258    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8440   -0.9036   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9088   -0.7627    0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6378   -1.9992    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9296   -0.3006    1.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5490   -3.1015   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5218   -3.7352    0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -3.2917   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END


  Mrv0541 04251301062D          

 20 20  0  0  0  0            999 V2000
    0.4125    3.1895    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   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
    0.7145    1.2375    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
    1.4289    0.0000    0.0000 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   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
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.0461    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  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
  7 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258766

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H23N2O3PS/c1-7-16-19(20,17-10(2)3)18-11-8-14-12(15-9-11)13(4,5)6/h8-10H,7H2,1-6H3

> <INCHI_KEY>
AWYOMXWDGWUJHS-UHFFFAOYSA-N

> <FORMULA>
C13H23N2O3PS

> <MOLECULAR_WEIGHT>
318.372

> <EXACT_MASS>
318.116699814

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.20530254059404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O-2-tert-butylpyrimidin-5-yl O-ethyl O-propan-2-yl phosphorothioate

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
4.365367059666667

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.5604841013133941

> <JCHEM_POLAR_SURFACE_AREA>
53.47

> <JCHEM_REFRACTIVITY>
84.77440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-2-tert-butylpyrimidin-5-yl O-ethyl O-isopropyl phosphorothioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258766
     RDKit          3D
Tebupirimfos
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.6020    3.2164   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946    2.3169   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9972    1.0097   -0.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428   -0.1001    0.4715 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0850    0.6568    1.7683 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903   -0.6820   -0.7243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.4692   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    0.6715   -1.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    0.8140   -0.8426 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0964   -0.1077   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5472    0.1124    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2432   -1.2322   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7285    0.5634    1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0302    1.1419   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -1.2155    0.3029 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -1.4254    0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -1.3863    1.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139   -1.5974    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1757   -1.1739    0.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0049   -2.9983   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6004    4.2427   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3362    3.2165   -1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    2.7651   -0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    2.5518    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975    2.5303   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    1.4244   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962   -2.0308   -0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -1.1202   -1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443   -1.4512    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3715   -0.3123    2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7831    0.7893    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0673    1.4395    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0444    1.5429   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000    1.9964   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    0.7211   -1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844   -2.3258    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8440   -0.9036   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9088   -0.7627    0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6378   -1.9992    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9296   -0.3006    1.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5490   -3.1015   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5218   -3.7352    0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -3.2917   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 25-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-13         0                                  
HETATM    1  S   UNK     0       0.770   5.954   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0       0.000   4.620   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.310   3.286   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.080   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.080   1.953   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   10   16                                                       
CONECT   16   15    7                                                       
CONECT   17    2   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0258766
HETATM    1  C1  UNL     1      -3.602   3.216  -0.748  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.595   2.317  -0.046  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.997   1.010  -0.290  1.00  0.00           O  
HETATM    4  P1  UNL     1      -1.943  -0.100   0.472  1.00  0.00           P  
HETATM    5  S1  UNL     1      -1.085   0.657   1.768  1.00  0.00           S  
HETATM    6  O2  UNL     1      -0.890  -0.682  -0.724  1.00  0.00           O  
HETATM    7  C3  UNL     1       0.478  -0.469  -0.548  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.083   0.671  -1.046  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.389   0.814  -0.843  1.00  0.00           N  
HETATM   10  C5  UNL     1       3.096  -0.108  -0.178  1.00  0.00           C  
HETATM   11  C6  UNL     1       4.547   0.112   0.025  1.00  0.00           C  
HETATM   12  C7  UNL     1       5.243  -1.232  -0.215  1.00  0.00           C  
HETATM   13  C8  UNL     1       4.729   0.563   1.466  1.00  0.00           C  
HETATM   14  C9  UNL     1       5.030   1.142  -0.940  1.00  0.00           C  
HETATM   15  N2  UNL     1       2.502  -1.215   0.303  1.00  0.00           N  
HETATM   16  C10 UNL     1       1.193  -1.425   0.136  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.873  -1.386   1.040  1.00  0.00           O  
HETATM   18  C11 UNL     1      -3.914  -1.597   0.141  1.00  0.00           C  
HETATM   19  C12 UNL     1      -5.176  -1.174   0.881  1.00  0.00           C  
HETATM   20  C13 UNL     1      -4.005  -2.998  -0.377  1.00  0.00           C  
HETATM   21  H1  UNL     1      -3.600   4.243  -0.328  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.336   3.216  -1.834  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.617   2.765  -0.690  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.494   2.552   1.038  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.598   2.530  -0.499  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.487   1.424  -1.589  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.496  -2.031  -0.444  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.872  -1.120  -1.118  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.844  -1.451   0.697  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.371  -0.312   2.085  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.783   0.789   1.651  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.067   1.439   1.623  1.00  0.00           H  
HETATM   33  H13 UNL     1       6.044   1.543  -0.698  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.300   1.996  -0.918  1.00  0.00           H  
HETATM   35  H15 UNL     1       4.964   0.721  -1.965  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.684  -2.326   0.513  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.844  -0.904  -0.740  1.00  0.00           H  
HETATM   38  H18 UNL     1      -5.909  -0.763   0.139  1.00  0.00           H  
HETATM   39  H19 UNL     1      -5.638  -1.999   1.440  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.930  -0.301   1.547  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.549  -3.102  -1.389  1.00  0.00           H  
HETATM   42  H22 UNL     1      -3.522  -3.735   0.285  1.00  0.00           H  
HETATM   43  H23 UNL     1      -5.091  -3.292  -0.511  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4
CONECT    4    5    5    6   17
CONECT    6    7
CONECT    7    8    8   16
CONECT    8    9   26
CONECT    9   10   10
CONECT   10   11   15
CONECT   11   12   13   14
CONECT   12   27   28   29
CONECT   13   30   31   32
CONECT   14   33   34   35
CONECT   15   16   16
CONECT   16   36
CONECT   17   18
CONECT   18   19   20   37
CONECT   19   38   39   40
CONECT   20   41   42   43
END

HMDB0258766
     RDKit          3D
Tebupirimfos
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.6020    3.2164   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946    2.3169   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9972    1.0097   -0.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428   -0.1001    0.4715 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0850    0.6568    1.7683 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903   -0.6820   -0.7243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.4692   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    0.6715   -1.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    0.8140   -0.8426 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0964   -0.1077   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5472    0.1124    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2432   -1.2322   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7285    0.5634    1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0302    1.1419   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -1.2155    0.3029 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -1.4254    0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -1.3863    1.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139   -1.5974    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1757   -1.1739    0.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0049   -2.9983   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6004    4.2427   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3362    3.2165   -1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    2.7651   -0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    2.5518    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975    2.5303   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    1.4244   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962   -2.0308   -0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -1.1202   -1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443   -1.4512    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3715   -0.3123    2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7831    0.7893    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0673    1.4395    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0444    1.5429   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000    1.9964   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    0.7211   -1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844   -2.3258    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8440   -0.9036   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9088   -0.7627    0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6378   -1.9992    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9296   -0.3006    1.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5490   -3.1015   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5218   -3.7352    0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -3.2917   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
O-(2-(1,1-Dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) phosphorothioate	ChEBI
O-(2-Tert-butylpyrimidin-5-yl) O-ethyl O-isopropyl thiophosphate	ChEBI
Phosphorothioic acid, O-(2-(1,1-dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) ester	ChEBI
Phostebupirim	ChEBI
Tebupirimphos	ChEBI
O-(2-(1,1-Dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) phosphorothioic acid	Generator
O-(2-Tert-butylpyrimidin-5-yl) O-ethyl O-isopropyl thiophosphoric acid	Generator
Phosphorothioate, O-(2-(1,1-dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) ester	Generator

Chemical Formula

C₁₃H₂₃N₂O₃PS

Average Molecular Weight

318.372

Monoisotopic Molecular Weight

318.116699814

IUPAC Name

O-2-tert-butylpyrimidin-5-yl O-ethyl O-propan-2-yl phosphorothioate

Traditional Name

O-2-tert-butylpyrimidin-5-yl O-ethyl O-isopropyl phosphorothioate

CAS Registry Number

Not Available

SMILES

CCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C

InChI Identifier

InChI=1S/C13H23N2O3PS/c1-7-16-19(20,17-10(2)3)18-11-8-14-12(15-9-11)13(4,5)6/h8-10H,7H2,1-6H3

InChI Key

AWYOMXWDGWUJHS-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
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

organic thiophosphate (CHEBI:38951 )
organothiophosphate insecticide (CHEBI:38951 )
Organophosphorus insecticides (C18692 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0258766)

Not Available

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0258766)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.4	ALOGPS
logP	4.37	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	0.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.47 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	84.77 m³·mol⁻¹	ChemAxon
Polarizability	33.21 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]+	173.485	30932474
DeepCCS	[M-H]-	171.127	30932474
DeepCCS	[M-2H]-	204.013	30932474
DeepCCS	[M+Na]+	179.578	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	167.8	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.6	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	172.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tebupirimfos	CCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C	2507.3	Standard polar	33892256
Tebupirimfos	CCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C	1882.2	Standard non polar	33892256
Tebupirimfos	CCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C	1819.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tebupirimfos GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kbb-3091000000-e482925bb6fcfc44353f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tebupirimfos 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tebupirimfos 45V, Positive-QTOF	splash10-0udi-0950000000-69f7d979b099897396c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tebupirimfos 60V, Positive-QTOF	splash10-0udi-0910000000-38add9d4c6dc3c9b1dcb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tebupirimfos 30V, Positive-QTOF	splash10-004i-0290000000-176b5e76ef68801d2300	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tebupirimfos 15V, Positive-QTOF	splash10-00or-0095000000-91a7dde839fb7669e005	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tebupirimfos 75V, Positive-QTOF	splash10-0udi-2900000000-3f567a576a7d1fa8d3d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tebupirimfos 90V, Positive-QTOF	splash10-0zg0-5900000000-4c3cc7498ae0d242ad51	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tebupirimfos 10V, Positive-QTOF	splash10-004j-1291000000-4d0dc62832ebcc780ce4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tebupirimfos 20V, Positive-QTOF	splash10-0002-1290000000-9368f2f9b8099edef4a7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tebupirimfos 40V, Positive-QTOF	splash10-059l-9800000000-381851a99cde0191b3f9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tebupirimfos 10V, Negative-QTOF	splash10-00n0-0392000000-57fcec897ede61056ac4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tebupirimfos 20V, Negative-QTOF	splash10-002r-0290000000-9cc36c0cae92a541c630	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tebupirimfos 40V, Negative-QTOF	splash10-0002-3390000000-f5cdaf73ae60de86fbf3	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

84419

KEGG Compound ID

C18692

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tebupirimfos

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

38951

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Tebupirimfos (HMDB0258766)

MOL for HMDB0258766 (Tebupirimfos)

3D MOL for HMDB0258766 (Tebupirimfos)

3D SDF for HMDB0258766 (Tebupirimfos)

3D-SDF for HMDB0258766 (Tebupirimfos)

PDB for HMDB0258766 (Tebupirimfos)

3D PDB for HMDB0258766 (Tebupirimfos)

SMILES for HMDB0258766 (Tebupirimfos)

INCHI for HMDB0258766 (Tebupirimfos)

Structure for HMDB0258766 (Tebupirimfos)

3D Structure for HMDB0258766 (Tebupirimfos)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra