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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:51:37 UTC

Update Date

2022-03-07 02:57:14 UTC

HMDB ID

HMDB0041985

Secondary Accession Numbers

HMDB41985

Metabolite Identification

Common Name

Phosalone

Description

Phosalone, also known as agria 1060 a or fozalon, belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. Based on a literature review very few articles have been published on Phosalone.

Structure

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

HMDB0041985
     RDKit          3D
Phosalone
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.6215   -3.4284   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -2.2355   -0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.4268    0.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488    0.0941    0.5161 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5813    0.5222    2.1510 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5621    1.1569    0.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    2.0965   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024    3.4418    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6554    0.3943   -0.7747 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -0.6781   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9835   -0.4149   -0.8154 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072   -0.7422   -2.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589   -1.2178   -2.9860 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6517   -0.5172   -2.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1488   -0.0605   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3886    0.3334   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    0.7423    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1414    1.1756    1.2877 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5011    0.7912    1.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    0.4073    1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0907    0.0152   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562   -3.7865   -1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139   -4.1278    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5087   -2.9461    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9302   -1.7387   -1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -2.6897   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    2.1281   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.1017   -1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    3.1589    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    4.1693   -0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288    3.6254    0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -1.7580   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715   -0.4703    0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2355    0.2797   -1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6249    1.1280    2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351    0.4767    1.8559 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  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 16 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv1652305271900262D          

 21 22  0  0  0  0            999 V2000
   -1.2778    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453    2.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932    1.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8607    2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216    2.5658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476    3.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    2.8207    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080    3.6053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 13  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 12  2  0  0  0  0
 16  3  1  0  0  0  0
 17  4  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 19  2  0  0  0  0
 21  8  1  0  0  0  0
 21 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041985

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=S)(OCC)SCN1C(=O)OC2=C1C=CC(Cl)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H15ClNO4PS2/c1-3-16-19(20,17-4-2)21-8-14-10-6-5-9(13)7-11(10)18-12(14)15/h5-7H,3-4,8H2,1-2H3

> <INCHI_KEY>
IOUNQDKNJZEDEP-UHFFFAOYSA-N

> <FORMULA>
C12H15ClNO4PS2

> <MOLECULAR_WEIGHT>
367.809

> <EXACT_MASS>
366.986863572

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
35.01950130558313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O,O-diethyl {[(6-chloro-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl)methyl]sulfanyl}phosphonothioate

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.7454628896666655

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3170141725063043

> <JCHEM_POLAR_SURFACE_AREA>
48.0

> <JCHEM_REFRACTIVITY>
89.24240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosalone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041985
     RDKit          3D
Phosalone
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.6215   -3.4284   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -2.2355   -0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.4268    0.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488    0.0941    0.5161 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5813    0.5222    2.1510 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5621    1.1569    0.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    2.0965   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024    3.4418    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6554    0.3943   -0.7747 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -0.6781   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9835   -0.4149   -0.8154 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072   -0.7422   -2.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589   -1.2178   -2.9860 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6517   -0.5172   -2.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1488   -0.0605   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3886    0.3334   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    0.7423    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1414    1.1756    1.2877 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5011    0.7912    1.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    0.4073    1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0907    0.0152   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562   -3.7865   -1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139   -4.1278    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5087   -2.9461    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9302   -1.7387   -1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -2.6897   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    2.1281   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.1017   -1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    3.1589    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    4.1693   -0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288    3.6254    0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -1.7580   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715   -0.4703    0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2355    0.2797   -1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6249    1.1280    2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351    0.4767    1.8559 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  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 16 34  1  0
 19 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.385   2.807   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.938   5.187   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.921   3.283   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.473   4.711   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       8.788  -0.770   0.000  0.00  0.00          Cl+0
HETATM   14  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.600   4.789   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.329   5.741   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0       0.864   5.265   0.000  0.00  0.00           P+0
HETATM   20  S   UNK     0       0.388   6.730   0.000  0.00  0.00           S+0
HETATM   21  S   UNK     0       1.340   3.801   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   16                                                       
CONECT    4    2   17                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8   14   21                                                       
CONECT    9    5    7   13                                                  
CONECT   10    6   11   14                                                  
CONECT   11    7   10   18                                                  
CONECT   12   14   15   18                                                  
CONECT   13    9                                                            
CONECT   14    8   10   12                                                  
CONECT   15   12                                                            
CONECT   16    3   19                                                       
CONECT   17    4   19                                                       
CONECT   18   11   12                                                       
CONECT   19   16   17   20   21                                             
CONECT   20   19                                                            
CONECT   21    8   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0041985
HETATM    1  C1  UNL     1      -3.622  -3.428  -0.187  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.678  -2.236  -0.489  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.798  -1.427   0.619  1.00  0.00           O  
HETATM    4  P1  UNL     1      -2.249   0.094   0.516  1.00  0.00           P  
HETATM    5  S1  UNL     1      -1.581   0.522   2.151  1.00  0.00           S  
HETATM    6  O2  UNL     1      -3.562   1.157   0.290  1.00  0.00           O  
HETATM    7  C3  UNL     1      -3.367   2.096  -0.702  1.00  0.00           C  
HETATM    8  C4  UNL     1      -3.602   3.442   0.120  1.00  0.00           C  
HETATM    9  S2  UNL     1      -0.655   0.394  -0.775  1.00  0.00           S  
HETATM   10  C5  UNL     1       0.726  -0.678  -0.244  1.00  0.00           C  
HETATM   11  N1  UNL     1       1.984  -0.415  -0.815  1.00  0.00           N  
HETATM   12  C6  UNL     1       2.407  -0.742  -2.078  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.659  -1.218  -2.986  1.00  0.00           O  
HETATM   14  O4  UNL     1       3.652  -0.517  -2.148  1.00  0.00           O  
HETATM   15  C7  UNL     1       4.149  -0.061  -1.042  1.00  0.00           C  
HETATM   16  C8  UNL     1       5.389   0.333  -0.568  1.00  0.00           C  
HETATM   17  C9  UNL     1       5.545   0.742   0.735  1.00  0.00           C  
HETATM   18 CL1  UNL     1       7.141   1.176   1.288  1.00  0.00          CL  
HETATM   19  C10 UNL     1       4.501   0.791   1.659  1.00  0.00           C  
HETATM   20  C11 UNL     1       3.270   0.407   1.137  1.00  0.00           C  
HETATM   21  C12 UNL     1       3.091   0.015  -0.133  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.056  -3.787  -1.144  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.114  -4.128   0.435  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.509  -2.946   0.366  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.930  -1.739  -1.400  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.630  -2.690  -0.567  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.353   2.128  -1.313  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.600   2.102  -1.370  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.110   3.159   1.141  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.973   4.169  -0.325  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.629   3.625   0.317  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.437  -1.758  -0.202  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.772  -0.470   0.895  1.00  0.00           H  
HETATM   34  H13 UNL     1       6.236   0.280  -1.223  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.625   1.128   2.651  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.435   0.477   1.856  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4
CONECT    4    5    5    6    9
CONECT    6    7
CONECT    7    8   27   28
CONECT    8   29   30   31
CONECT    9   10
CONECT   10   11   32   33
CONECT   11   12   21
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   34
CONECT   17   18   19   19
CONECT   19   20   35
CONECT   20   21   21   36
END

HMDB0041985
     RDKit          3D
Phosalone
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.6215   -3.4284   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -2.2355   -0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.4268    0.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488    0.0941    0.5161 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5813    0.5222    2.1510 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5621    1.1569    0.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    2.0965   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024    3.4418    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6554    0.3943   -0.7747 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -0.6781   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9835   -0.4149   -0.8154 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072   -0.7422   -2.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589   -1.2178   -2.9860 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6517   -0.5172   -2.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1488   -0.0605   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3886    0.3334   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    0.7423    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1414    1.1756    1.2877 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5011    0.7912    1.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    0.4073    1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0907    0.0152   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562   -3.7865   -1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139   -4.1278    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5087   -2.9461    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9302   -1.7387   -1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -2.6897   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    2.1281   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.1017   -1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    3.1589    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    4.1693   -0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288    3.6254    0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -1.7580   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715   -0.4703    0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2355    0.2797   -1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6249    1.1280    2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351    0.4767    1.8559 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  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 16 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[O,O-(Diethyldithiophosphoryl)methyl]-6-chlorobenzoxazolinone	ChEBI
Agria 1060 a	ChEBI
Phosphorodithioic acid, S-((6-chloro-2-oxo-3(2H)-benzoxazolyl)methyl) O,O-diethyl ester	ChEBI
S-[(6-Chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)methyl] O,O-diethyl dithiophosphate	ChEBI
Phosphorodithioate, S-((6-chloro-2-oxo-3(2H)-benzoxazolyl)methyl) O,O-diethyl ester	Generator
S-[(6-Chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)methyl] O,O-diethyl dithiophosphoric acid	Generator
Azofene	HMDB
Benzophosphate	HMDB
Fosalon	HMDB
Fosalone	HMDB
Fozalon	HMDB
Phasolon	HMDB
Phosalon	HMDB
Phozalon	HMDB
Rubitox	HMDB
S-[(6-Chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)methyl] O,O-diethyl phosphorodithioate	HMDB
Zolone	HMDB
Zolone PM	HMDB
Zoolon	HMDB
Fozalone	HMDB
Phoazlone	HMDB
Phozalone	HMDB

Chemical Formula

C₁₂H₁₅ClNO₄PS₂

Average Molecular Weight

367.809

Monoisotopic Molecular Weight

366.986863572

IUPAC Name

O,O-diethyl {[(6-chloro-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl)methyl]sulfanyl}phosphonothioate

Traditional Name

phosalone

CAS Registry Number

2310-17-0

SMILES

CCOP(=S)(OCC)SCN1C(=O)OC2=C1C=CC(Cl)=C2

InChI Identifier

InChI=1S/C12H15ClNO4PS2/c1-3-16-19(20,17-4-2)21-8-14-10-6-5-9(13)7-11(10)18-12(14)15/h5-7H,3-4,8H2,1-2H3

InChI Key

IOUNQDKNJZEDEP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazoles

Sub Class

Benzoxazolones

Direct Parent

Benzoxazolones

Alternative Parents

Substituents

Benzoxazolone
Aryl chloride
Aryl halide
Dithiophosphate o-ester
Dithiophosphate s-ester
Benzenoid
Azole
Oxazole
Heteroaromatic compound
Organic dithiophosphate
Organothiophosphorus compound
Sulfenyl compound
Oxacycle
Azacycle
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:8121 )
1,3-benzoxazoles (CHEBI:8121 )
organochlorine insecticide (CHEBI:8121 )
organothiophosphate insecticide (CHEBI:8121 )
Organophosphorus insecticides (C11028 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041985)

Source

Exogenous

Exogenous (HMDB: HMDB0041985)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0041985)

Agriculture

Pesticide

Acaricide (HMDB: HMDB0041985)

Biological role

Modulator

Inhibitor

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0041985)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0041985)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	46 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.003 mg/mL at 25 °C	Not Available
LogP	4.38	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	3.96	ALOGPS
logP	3.75	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	89.24 m³·mol⁻¹	ChemAxon
Polarizability	35.02 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]+	172.564	30932474
DeepCCS	[M-H]-	170.206	30932474
DeepCCS	[M-2H]-	203.091	30932474
DeepCCS	[M+Na]+	178.657	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	168.3	32859911
AllCCS	[M+NH4]+	172.8	32859911
AllCCS	[M+Na]+	173.4	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.5 minutes	32390414
Predicted by Siyang on May 30, 2022	17.2529 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2403.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	436.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	134.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	589.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	594.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1278.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	482.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1480.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	278.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phosalone	CCOP(=S)(OCC)SCN1C(=O)OC2=C1C=CC(Cl)=C2	3903.1	Standard polar	33892256
Phosalone	CCOP(=S)(OCC)SCN1C(=O)OC2=C1C=CC(Cl)=C2	2527.7	Standard non polar	33892256
Phosalone	CCOP(=S)(OCC)SCN1C(=O)OC2=C1C=CC(Cl)=C2	2509.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phosalone EI-B (Non-derivatized)	splash10-001i-3901000000-80a2a63054e8b0fc3477	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phosalone EI-B (Non-derivatized)	splash10-001i-3901000000-80a2a63054e8b0fc3477	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosalone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-1907000000-47d821da4a8328facc68	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosalone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-5900000000-1b880221f417da6800b1	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 - Phosalone 75V, Positive-QTOF	splash10-0aor-9100000000-206bc8b2783f3f3c660b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 30V, Positive-QTOF	splash10-01qa-9600000000-b57d5aaf11dcb79c0858	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 15V, Positive-QTOF	splash10-001i-1903000000-e8ce8cf35e03b1822842	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 30V, Positive-QTOF	splash10-01qa-9600000000-f5040fecc14bae872dc9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 60V, Positive-QTOF	splash10-067i-9200000000-04f05ba8b1a130a8e632	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 45V, Positive-QTOF	splash10-067j-9300000000-7c42db87eca9af7d5af4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 60V, Positive-QTOF	splash10-067i-9200000000-17020a34c60786caa0df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 90V, Positive-QTOF	splash10-0aor-9100000000-e80fc69b9148803c6b88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosalone 75V, Positive-QTOF	splash10-0aor-9200000000-206bc8b2783f3f3c660b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 10V, Positive-QTOF	splash10-014i-0191000000-7bddd5607e4d88fd13f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 20V, Positive-QTOF	splash10-0fi9-0901000000-77a74f9f40bfc6df4e35	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 40V, Positive-QTOF	splash10-03fr-0910000000-c2ed59c980525dd525b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 10V, Negative-QTOF	splash10-014i-0749000000-eaccb0c5acac66311305	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 20V, Negative-QTOF	splash10-02t9-0895000000-21b8f9d07e2d377303c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 40V, Negative-QTOF	splash10-0006-0391000000-3b3070354a73b33d5a33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 10V, Positive-QTOF	splash10-001i-0900000000-c358770cc9299e9a7e03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 20V, Positive-QTOF	splash10-001i-0900000000-4baf6635b8db64ffca13	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 40V, Positive-QTOF	splash10-0h40-0900000000-9aa4ff0cbbe935b3ff75	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 10V, Negative-QTOF	splash10-0zfr-0911000000-4bf78aa6a97c7cbdf9b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 20V, Negative-QTOF	splash10-0pb9-0900000000-ff96605f966d88ef5551	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosalone 40V, Negative-QTOF	splash10-00yi-2910000000-3fcdef2bb99fac3a8b03	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4629

KEGG Compound ID

C11028

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phosalone

METLIN ID

Not Available

PubChem Compound

4793

PDB ID

Not Available

ChEBI ID

8121

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

Not Available

Showing metabocard for Phosalone (HMDB0041985)

MOL for HMDB0041985 (Phosalone)

3D MOL for HMDB0041985 (Phosalone)

3D SDF for HMDB0041985 (Phosalone)

3D-SDF for HMDB0041985 (Phosalone)

PDB for HMDB0041985 (Phosalone)

3D PDB for HMDB0041985 (Phosalone)

SMILES for HMDB0041985 (Phosalone)

INCHI for HMDB0041985 (Phosalone)

Structure for HMDB0041985 (Phosalone)

3D Structure for HMDB0041985 (Phosalone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra