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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:15:25 UTC

Update Date

2021-09-26 22:59:17 UTC

HMDB ID

HMDB0248807

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Azinphos-methyl

Description

Azinphos-methyl, also known as guthion, belongs to the class of organic compounds known as benzotriazine organothiophosphates. These are aromatic compounds containing a benzo-1,2,3-triazine, which is substituted by an organothiophosphate group at the 3-position. Their general structure is R-CSP(=S)(OR')OR'', where R=benzo-1,2,3-triazine, R',R\" = any atom. Based on a literature review a significant number of articles have been published on Azinphos-methyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). Azinphos-methyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Azinphos-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

HMDB0248807
     RDKit          3D
Azinphos-methyl
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.0692    2.1258    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750    0.8274   -0.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477   -0.2982    0.7846 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.2524   -0.3917    2.3096 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178   -1.8143    0.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8993   -1.8309   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876    0.0850    1.0378 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998   -1.1235    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945   -0.8413    0.3341 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -1.3956    1.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9032   -1.1926    1.6000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979   -0.3706    0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426   -0.1357    0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6870    0.6728    0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0720    1.2800   -0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413    1.0592   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.2442   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6504   -0.0303   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    0.5138   -1.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258    2.3170    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0491    2.7912   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    2.4425    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0146   -2.6289   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6110   -1.9238    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0566   -0.8331   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118   -1.1373   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470   -2.1275    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4329   -0.6049    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491    0.8724    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188    1.9289   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2210    1.5201   -1.9775 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
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18  9  1  0
 17 12  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
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
M  END


  Mrv0541 02241204172D          

 19 20  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248807

> <DATABASE_NAME>
hmdb

> <SMILES>
COP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3

> <INCHI_KEY>
CJJOSEISRRTUQB-UHFFFAOYSA-N

> <FORMULA>
C10H12N3O3PS2

> <MOLECULAR_WEIGHT>
317.324

> <EXACT_MASS>
317.005769157

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.621752172740663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O,O-dimethyl {[(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)methyl]sulfanyl}phosphonothioate

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
3.2447699109999997

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8078750540877

> <JCHEM_POLAR_SURFACE_AREA>
63.49

> <JCHEM_REFRACTIVITY>
83.6381

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O,O-dimethyl [(4-oxo-1,2,3-benzotriazin-3-yl)methyl]sulfanylphosphonothioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248807
     RDKit          3D
Azinphos-methyl
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.0692    2.1258    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750    0.8274   -0.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477   -0.2982    0.7846 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.2524   -0.3917    2.3096 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178   -1.8143    0.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8993   -1.8309   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876    0.0850    1.0378 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998   -1.1235    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945   -0.8413    0.3341 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -1.3956    1.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9032   -1.1926    1.6000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979   -0.3706    0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426   -0.1357    0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6870    0.6728    0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0720    1.2800   -0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413    1.0592   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.2442   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6504   -0.0303   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    0.5138   -1.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258    2.3170    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0491    2.7912   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    2.4425    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0146   -2.6289   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6110   -1.9238    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0566   -0.8331   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118   -1.1373   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470   -2.1275    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4329   -0.6049    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491    0.8724    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188    1.9289   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2210    1.5201   -1.9775 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
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18  9  1  0
 17 12  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
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0       8.002  -3.080   0.000  0.00  0.00           P+0
HETATM    4  S   UNK     0       7.232  -4.414   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0       8.772  -1.746   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.312  -1.746   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       9.336  -3.850   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      12.003  -3.850   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      13.337  -3.080   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      14.671  -3.850   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      14.671  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.004  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.671  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    7                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    9   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0248807
HETATM    1  C1  UNL     1      -4.069   2.126   0.223  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.175   0.827  -0.240  1.00  0.00           O  
HETATM    3  P1  UNL     1      -3.448  -0.298   0.785  1.00  0.00           P  
HETATM    4  S1  UNL     1      -4.252  -0.392   2.310  1.00  0.00           S  
HETATM    5  O2  UNL     1      -3.618  -1.814   0.047  1.00  0.00           O  
HETATM    6  C2  UNL     1      -4.899  -1.831  -0.523  1.00  0.00           C  
HETATM    7  S2  UNL     1      -1.388   0.085   1.038  1.00  0.00           S  
HETATM    8  C3  UNL     1      -0.400  -1.124   0.146  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.994  -0.841   0.334  1.00  0.00           N  
HETATM   10  N2  UNL     1       1.620  -1.396   1.349  1.00  0.00           N  
HETATM   11  N3  UNL     1       2.903  -1.193   1.600  1.00  0.00           N  
HETATM   12  C4  UNL     1       3.598  -0.371   0.762  1.00  0.00           C  
HETATM   13  C5  UNL     1       4.943  -0.136   0.995  1.00  0.00           C  
HETATM   14  C6  UNL     1       5.687   0.673   0.196  1.00  0.00           C  
HETATM   15  C7  UNL     1       5.072   1.280  -0.888  1.00  0.00           C  
HETATM   16  C8  UNL     1       3.741   1.059  -1.133  1.00  0.00           C  
HETATM   17  C9  UNL     1       3.009   0.244  -0.321  1.00  0.00           C  
HETATM   18  C10 UNL     1       1.650  -0.030  -0.505  1.00  0.00           C  
HETATM   19  O3  UNL     1       1.092   0.514  -1.478  1.00  0.00           O  
HETATM   20  H1  UNL     1      -3.126   2.317   0.778  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.049   2.791  -0.671  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.968   2.442   0.810  1.00  0.00           H  
HETATM   23  H4  UNL     1      -5.015  -2.629  -1.261  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.611  -1.924   0.341  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.057  -0.833  -0.988  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.612  -1.137  -0.944  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.647  -2.127   0.560  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.433  -0.605   1.838  1.00  0.00           H  
HETATM   29  H10 UNL     1       6.749   0.872   0.360  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.619   1.929  -1.550  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.221   1.520  -1.978  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   18
CONECT   10   11   11
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18
CONECT   18   19   19
END

HMDB0248807
     RDKit          3D
Azinphos-methyl
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.0692    2.1258    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750    0.8274   -0.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477   -0.2982    0.7846 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.2524   -0.3917    2.3096 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178   -1.8143    0.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8993   -1.8309   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876    0.0850    1.0378 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998   -1.1235    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945   -0.8413    0.3341 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -1.3956    1.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9032   -1.1926    1.6000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979   -0.3706    0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426   -0.1357    0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6870    0.6728    0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0720    1.2800   -0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413    1.0592   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.2442   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6504   -0.0303   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    0.5138   -1.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258    2.3170    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0491    2.7912   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    2.4425    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0146   -2.6289   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6110   -1.9238    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0566   -0.8331   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118   -1.1373   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470   -2.1275    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4329   -0.6049    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491    0.8724    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188    1.9289   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2210    1.5201   -1.9775 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
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18  9  1  0
 17 12  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
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioate	ChEBI
Azinphos methyl	ChEBI
Azinphosmethyl	ChEBI
Guthion	ChEBI
O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphate	ChEBI
O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphate	ChEBI
Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester	ChEBI
3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioic acid	Generator
O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphoric acid	Generator
O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphoric acid	Generator
Phosphorodithioate, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester	Generator

Chemical Formula

C₁₀H₁₂N₃O₃PS₂

Average Molecular Weight

317.324

Monoisotopic Molecular Weight

317.005769157

IUPAC Name

O,O-dimethyl {[(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)methyl]sulfanyl}phosphonothioate

Traditional Name

O,O-dimethyl [(4-oxo-1,2,3-benzotriazin-3-yl)methyl]sulfanylphosphonothioate

CAS Registry Number

Not Available

SMILES

COP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3

InChI Key

CJJOSEISRRTUQB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzotriazine organothiophosphates. These are aromatic compounds containing a benzo-1,2,3-triazine, which is substituted by an organothiophosphate group at the 3-position. Their general structure is R-CSP(=S)(OR')OR'', where R=benzo-1,2,3-triazine, R',R\" = any atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzo-1,2,3-triazines

Sub Class

Benzotriazine organothiophosphates

Direct Parent

Benzotriazine organothiophosphates

Alternative Parents

Substituents

Benzotriazine organothiophosphate
Triazinone
Triazine
Dithiophosphate s-ester
Benzenoid
1,2,3-triazine
Dithiophosphate o-ester
Heteroaromatic compound
Organic dithiophosphate
Lactam
Azacycle
Sulfenyl compound
Organothiophosphorus compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic thiophosphate (CHEBI:2953 )
organothiophosphate insecticide (CHEBI:2953 )
benzotriazines (CHEBI:2953 )
Organophosphorus insecticides (C11018 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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	2.75	ALOGPS
logP	3.24	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.64 m³·mol⁻¹	ChemAxon
Polarizability	29.62 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+H]+	156.566	30932474
DeepCCS	[M-H]-	154.208	30932474
DeepCCS	[M-2H]-	187.465	30932474
DeepCCS	[M+Na]+	162.659	30932474
AllCCS	[M+H]+	161.3	32859911
AllCCS	[M+H-H2O]+	158.5	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	163.1	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azinphos-methyl	COP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O	3450.3	Standard polar	33892256
Azinphos-methyl	COP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O	2407.3	Standard non polar	33892256
Azinphos-methyl	COP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O	2465.2	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 - Azinphos-methyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-0910000000-8a90862fb34d7f1de4d6	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azinphos-methyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0in9-8900000000-dcab6b11e3ab3e51c6c8	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 - Azinphos-methyl 50V, Positive-QTOF	splash10-008c-0900000000-c3d2041851aea43793d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 30V, Positive-QTOF	splash10-001i-0900000000-d45bfd942d49cb4291ae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 90V, Positive-QTOF	splash10-0kdj-9300000000-8aab23fdf42981012983	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 50V, Positive-QTOF	splash10-008c-0900000000-1af926d96f15ea4fe029	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 75V, Positive-QTOF	splash10-0kdm-9600000000-87f03e4a5118de93472b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 20V, Positive-QTOF	splash10-001i-0900000000-65ca1a571d6e6181a088	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 10V, Positive-QTOF	splash10-03e9-0900000000-c34b6732021b15900ca6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 30V, Positive-QTOF	splash10-001i-0900000000-7cfe94f327d288d4482c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 40V, Positive-QTOF	splash10-001i-0900000000-56fb2b538788f6a5dd63	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 30V, Positive-QTOF	splash10-000x-0900000000-02de58086414fbca0a4b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 35V, Positive-QTOF	splash10-000x-1900000000-eacce6bcbada6302fcfb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 15V, Positive-QTOF	splash10-03ec-0910000000-4f5411792d4477abc588	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 45V, Positive-QTOF	splash10-0006-1900000000-0d479bb903e25e1f854e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azinphos-methyl 60V, Positive-QTOF	splash10-0kbg-5900000000-3e0b563fe56090b9433a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 10V, Positive-QTOF	splash10-014l-0639000000-d7afc7588998311cc61f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 20V, Positive-QTOF	splash10-0gb9-6908000000-2adf23de316e0ef841d4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 40V, Positive-QTOF	splash10-0007-6900000000-ab0ac3300b9628fd5fa4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 10V, Negative-QTOF	splash10-014i-0119000000-6b01cea6b4efafb87ffc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 20V, Negative-QTOF	splash10-000i-0390000000-2c07ac5163df5ab1dc15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 40V, Negative-QTOF	splash10-0006-1900000000-4a556662783ce60fac92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 10V, Positive-QTOF	splash10-03e9-0900000000-c86324755309401cbaea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 20V, Positive-QTOF	splash10-01q9-0900000000-558e5a824d096c620192	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 40V, Positive-QTOF	splash10-05fr-5900000000-6248de11ddfc5a8e385e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 10V, Negative-QTOF	splash10-00di-0902000000-8064bfc10805102a22bc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azinphos-methyl 20V, Negative-QTOF	splash10-00di-2900000000-e2f755731cfbdd47a562	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

2181

KEGG Compound ID

C11018

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azinphos-methyl

METLIN ID

Not Available

PubChem Compound

2268

PDB ID

Not Available

ChEBI ID

2953

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1309221

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 Azinphos-methyl (HMDB0248807)

MOL for HMDB0248807 (Azinphos-methyl)

3D MOL for HMDB0248807 (Azinphos-methyl)

3D SDF for HMDB0248807 (Azinphos-methyl)

3D-SDF for HMDB0248807 (Azinphos-methyl)

PDB for HMDB0248807 (Azinphos-methyl)

3D PDB for HMDB0248807 (Azinphos-methyl)

SMILES for HMDB0248807 (Azinphos-methyl)

INCHI for HMDB0248807 (Azinphos-methyl)

Structure for HMDB0248807 (Azinphos-methyl)

3D Structure for HMDB0248807 (Azinphos-methyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra