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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:12:41 UTC

Update Date

2021-09-26 22:59:14 UTC

HMDB ID

HMDB0248763

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Azamethiphos

Description

azamethiphos, also known as actogard, belongs to the class of organic compounds known as oxazolopyridines. These are polycyclic compounds containing an oxazole ring fused to a pyridine ring. Based on a literature review very few articles have been published on azamethiphos. This compound has been identified in human blood as reported by (PMID: 31557052 ). Azamethiphos is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Azamethiphos 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

HMDB0248763
     RDKit          3D
Azamethiphos
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.4934    2.0096    1.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    2.1597    0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276    0.6612   -0.2999 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.6370    0.1960   -1.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -0.4943    0.9521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954   -1.7225    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    0.9233   -0.8167 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949   -0.6600   -0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -0.4912   -1.0692 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.5997   -2.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117   -0.8644   -3.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -0.3823   -2.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818   -0.1289   -1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8898    0.1592   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503    0.3787    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4543    0.7512    1.7807 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7871    0.3075    1.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145    0.0237    1.0704 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.1985   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1535    1.1593    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1446    2.9073    1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392    1.8599    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8346   -2.5017    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322   -1.8672   -0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4580   -1.9019    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -1.3487   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235   -1.0202    0.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665    0.2064   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047    0.4783    2.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  9  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
 14 28  1  0
 17 29  1  0
M  END

  Mrv0541 04251300582D          

 19 20  0  0  0  0            999 V2000
    0.6065    1.9652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331    2.4949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628    1.4553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5758    2.0074    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
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248763

> <DATABASE_NAME>
hmdb

> <SMILES>
COP(=O)(OC)SCN1C(=O)OC2=CC(Cl)=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3

> <INCHI_KEY>
VNKBTWQZTQIWDV-UHFFFAOYSA-N

> <FORMULA>
C9H10ClN2O5PS

> <MOLECULAR_WEIGHT>
324.678

> <EXACT_MASS>
323.973656349

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.0785549537352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl [({6-chloro-2-oxo-2H,3H-[1,3]oxazolo[4,5-b]pyridin-3-yl}methyl)sulfanyl]phosphonate

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
1.5187624989999997

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9123416068847224

> <JCHEM_POLAR_SURFACE_AREA>
77.96

> <JCHEM_REFRACTIVITY>
69.9109

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azamethiphos

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248763
     RDKit          3D
Azamethiphos
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.4934    2.0096    1.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    2.1597    0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276    0.6612   -0.2999 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.6370    0.1960   -1.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -0.4943    0.9521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954   -1.7225    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    0.9233   -0.8167 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949   -0.6600   -0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -0.4912   -1.0692 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.5997   -2.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117   -0.8644   -3.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -0.3823   -2.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818   -0.1289   -1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8898    0.1592   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503    0.3787    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4543    0.7512    1.7807 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7871    0.3075    1.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145    0.0237    1.0704 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.1985   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1535    1.1593    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1446    2.9073    1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392    1.8599    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8346   -2.5017    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322   -1.8672   -0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4580   -1.9019    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -1.3487   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235   -1.0202    0.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665    0.2064   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047    0.4783    2.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  9  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
 14 28  1  0
 17 29  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  O   UNK     0       1.132   3.668   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0      -0.332   3.193   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      -0.808   4.657   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.315   4.977   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       0.143   1.728   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.924   0.237   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       7.591  -2.843   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.797   2.717   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.941   3.747   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5   18                                             
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    7   17                                                  
CONECT   17   16                                                            
CONECT   18    2   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0248763
HETATM    1  C1  UNL     1      -4.493   2.010   1.096  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.413   2.160   0.230  1.00  0.00           O  
HETATM    3  P1  UNL     1      -2.828   0.661  -0.300  1.00  0.00           P  
HETATM    4  O2  UNL     1      -3.637   0.196  -1.505  1.00  0.00           O  
HETATM    5  O3  UNL     1      -2.944  -0.494   0.952  1.00  0.00           O  
HETATM    6  C2  UNL     1      -3.395  -1.722   0.458  1.00  0.00           C  
HETATM    7  S1  UNL     1      -0.799   0.923  -0.817  1.00  0.00           S  
HETATM    8  C3  UNL     1       0.095  -0.660  -0.716  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.490  -0.491  -1.069  1.00  0.00           N  
HETATM   10  C4  UNL     1       2.014  -0.600  -2.302  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.412  -0.864  -3.377  1.00  0.00           O  
HETATM   12  O5  UNL     1       3.322  -0.382  -2.254  1.00  0.00           O  
HETATM   13  C5  UNL     1       3.682  -0.129  -1.003  1.00  0.00           C  
HETATM   14  C6  UNL     1       4.890   0.159  -0.400  1.00  0.00           C  
HETATM   15  C7  UNL     1       4.950   0.379   0.942  1.00  0.00           C  
HETATM   16 CL1  UNL     1       6.454   0.751   1.781  1.00  0.00          CL  
HETATM   17  C8  UNL     1       3.787   0.308   1.682  1.00  0.00           C  
HETATM   18  N2  UNL     1       2.614   0.024   1.070  1.00  0.00           N  
HETATM   19  C9  UNL     1       2.518  -0.199  -0.252  1.00  0.00           C  
HETATM   20  H1  UNL     1      -5.154   1.159   0.785  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.145   2.907   1.106  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.139   1.860   2.137  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.835  -2.502   1.054  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.132  -1.867  -0.602  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.458  -1.902   0.651  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.403  -1.349  -1.435  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.024  -1.020   0.332  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.766   0.206  -0.999  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.805   0.478   2.756  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4    5    7
CONECT    5    6
CONECT    6   23   24   25
CONECT    7    8
CONECT    8    9   26   27
CONECT    9   10   19
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   28
CONECT   15   16   17   17
CONECT   17   18   29
CONECT   18   19   19
END

HMDB0248763
     RDKit          3D
Azamethiphos
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.4934    2.0096    1.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    2.1597    0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276    0.6612   -0.2999 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.6370    0.1960   -1.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -0.4943    0.9521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954   -1.7225    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    0.9233   -0.8167 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949   -0.6600   -0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -0.4912   -1.0692 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.5997   -2.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117   -0.8644   -3.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -0.3823   -2.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818   -0.1289   -1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8898    0.1592   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503    0.3787    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4543    0.7512    1.7807 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7871    0.3075    1.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145    0.0237    1.0704 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.1985   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1535    1.1593    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1446    2.9073    1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392    1.8599    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8346   -2.5017    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322   -1.8672   -0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4580   -1.9019    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -1.3487   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235   -1.0202    0.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665    0.2064   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047    0.4783    2.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  9  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
 14 28  1  0
 17 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Chloro-3-dimethoxyphosphinoylthiomethyl-1,3-oxazolo(4,5-b)pyridin-2(3H)-one	ChEBI
S-((6-Chloro-2,3-dihydro-2-oxo-1,3-oxazolo-(4,5-b)pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate	ChEBI
S-((6-Chloro-2-oxooxazolo(4,5-b)pyridin-3(2H)-yl)methyl) O,O-dimethylphosphorothioate	ChEBI
S-6-Chloro-2,3-dihydro-2-oxo-1,3-oxazolo(4,5-b)pyridin-3-ylmethyl O,O-dimethyl phosphorothioate	ChEBI
S-[(6-Chloro-2-oxo[1,3]oxazolo[4,5-b]pyridin-3(2H)-yl)methyl] O,O-dimethyl thiophosphate	ChEBI
Actogard	Kegg
S-((6-Chloro-2,3-dihydro-2-oxo-1,3-oxazolo-(4,5-b)pyridin-3-yl)methyl) O,O-dimethyl phosphorothioic acid	Generator
S-((6-Chloro-2-oxooxazolo(4,5-b)pyridin-3(2H)-yl)methyl) O,O-dimethylphosphorothioic acid	Generator
S-6-Chloro-2,3-dihydro-2-oxo-1,3-oxazolo(4,5-b)pyridin-3-ylmethyl O,O-dimethyl phosphorothioic acid	Generator
S-[(6-Chloro-2-oxo[1,3]oxazolo[4,5-b]pyridin-3(2H)-yl)methyl] O,O-dimethyl thiophosphoric acid	Generator
S-6-chloro-2-Oxooxazol(4,5-6)-pyridin-3-yl methyl O,O-dimethylphosphorothioate	MeSH

Chemical Formula

C₉H₁₀ClN₂O₅PS

Average Molecular Weight

324.678

Monoisotopic Molecular Weight

323.973656349

IUPAC Name

dimethyl [({6-chloro-2-oxo-2H,3H-[1,3]oxazolo[4,5-b]pyridin-3-yl}methyl)sulfanyl]phosphonate

Traditional Name

azamethiphos

CAS Registry Number

Not Available

SMILES

COP(=O)(OC)SCN1C(=O)OC2=CC(Cl)=CN=C12

InChI Identifier

InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3

InChI Key

VNKBTWQZTQIWDV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxazolopyridines. These are polycyclic compounds containing an oxazole ring fused to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazolopyridines

Sub Class

Not Available

Direct Parent

Oxazolopyridines

Alternative Parents

Substituents

1,3-oxazolopyridine
Aryl chloride
Aryl halide
Pyridine
Azole
Oxazole
Heteroaromatic compound
Azacycle
Sulfenyl compound
Organothiophosphorus compound
Oxacycle
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine insecticide (CHEBI:38578 )
organic thiophosphate (CHEBI:38578 )
organothiophosphate insecticide (CHEBI:38578 )
organochlorine acaricide (CHEBI:38578 )
Organophosphorus insecticides (C18702 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0248763)
Extracellular (HMDB: HMDB0248763)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0248763)

Biological role

Modulator

Inhibitor

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0248763)

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	0.85	ALOGPS
logP	1.52	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.96 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.91 m³·mol⁻¹	ChemAxon
Polarizability	28.08 Å³	ChemAxon
Number of Rings	2	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-2H]-	190.999	30932474
DeepCCS	[M+Na]+	166.556	30932474
AllCCS	[M+H]+	164.1	32859911
AllCCS	[M+H-H2O]+	161.0	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azamethiphos	COP(=O)(OC)SCN1C(=O)OC2=CC(Cl)=CN=C12	3340.0	Standard polar	33892256
Azamethiphos	COP(=O)(OC)SCN1C(=O)OC2=CC(Cl)=CN=C12	2340.0	Standard non polar	33892256
Azamethiphos	COP(=O)(OC)SCN1C(=O)OC2=CC(Cl)=CN=C12	2259.2	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 - Azamethiphos GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0940000000-b248b56636ba11a1a640	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azamethiphos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a6r-3910000000-6ff700e902da75b9a3f5	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 10V, Positive-QTOF	splash10-00di-0029000000-5c01fbabb3ce9d470f79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 20V, Positive-QTOF	splash10-0229-1149000000-ccda22a475e9aabb7032	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 40V, Positive-QTOF	splash10-03di-0090000000-ec7cff833d47433d2e10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 10V, Negative-QTOF	splash10-00di-0029000000-be8b18c3678ddbe0c546	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 20V, Negative-QTOF	splash10-00fr-1298000000-a5a9b9816448d641d138	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 40V, Negative-QTOF	splash10-03di-0290000000-32d412767c009746eeab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 10V, Positive-QTOF	splash10-001i-0902000000-805b25d0fd323fee886d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 20V, Positive-QTOF	splash10-001i-0900000000-cd877a20054f464ca10e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 40V, Positive-QTOF	splash10-03di-0900000000-61b9dde5f7a20fec6ea7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 10V, Negative-QTOF	splash10-00di-0009000000-c4a8a2d2d33f3eaba8af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 20V, Negative-QTOF	splash10-01ox-9142000000-167147dc80929739ee2f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azamethiphos 40V, Negative-QTOF	splash10-067i-3900000000-354ca1cf82cae54ec513	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

64559

KEGG Compound ID

C18702

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azamethiphos

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

38578

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 Azamethiphos (HMDB0248763)

MOL for HMDB0248763 (Azamethiphos)

3D MOL for HMDB0248763 (Azamethiphos)

3D SDF for HMDB0248763 (Azamethiphos)

3D-SDF for HMDB0248763 (Azamethiphos)

PDB for HMDB0248763 (Azamethiphos)

3D PDB for HMDB0248763 (Azamethiphos)

SMILES for HMDB0248763 (Azamethiphos)

INCHI for HMDB0248763 (Azamethiphos)

Structure for HMDB0248763 (Azamethiphos)

3D Structure for HMDB0248763 (Azamethiphos)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra