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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:12:03 UTC

Update Date

2020-02-26 21:38:05 UTC

HMDB ID

HMDB0013035

Secondary Accession Numbers

HMDB13035

Metabolite Identification

Common Name

Paraoxon

Description

Paraoxon is an acetylcholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an opthamological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. It is easily absorbed through skin, and was used as an assassination weapon by the apartheid-era South African chemical weapons program Project Coast.

Structure

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

HMDB0013035
     RDKit          3D
Paraoxon
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.5060   -3.4698   -0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -2.1547    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -1.3092   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3837    0.1400    0.4313 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.5039    0.1584    1.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6376    1.4749   -0.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    2.4564    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298    3.6532   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750    0.3593    1.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.1473    0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -1.0779    0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218   -1.2977    0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.2788   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046   -0.4984   -0.7978 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.8023    0.4453   -1.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -1.7330   -0.6669 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2956    0.9552   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0116    1.1595    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6938   -3.6889   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5148   -3.5811   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4709   -4.3227    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -1.6642    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -2.3413    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213    2.0499    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    2.8057    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    3.3830   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210    4.2914   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5108    4.1941   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270   -1.8788    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144   -2.2590    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505    1.7362   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985    2.1456    0.0121 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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2  14   1  16  -1
M  END


  Mrv0541 02251208152D          

 18 18  0  0  0  0            999 V2000
   14.9839  -13.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9839  -12.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2693  -12.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2693  -11.2965    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2693  -10.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0943  -11.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5068  -12.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3318  -12.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4442  -11.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0317  -10.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4442   -9.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0317   -9.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2067   -9.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7942   -9.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2067  -10.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7942   -8.4381    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.2067   -7.7241    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.9692   -8.4381    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  CHG  2  16   1  17  -1
M  END
> <DATABASE_ID>
HMDB0013035

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

> <INCHI_KEY>
WYMSBXTXOHUIGT-UHFFFAOYSA-N

> <FORMULA>
C10H14NO6P

> <MOLECULAR_WEIGHT>
275.195

> <EXACT_MASS>
275.055873697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.971328827440267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
diethyl 4-nitrophenyl phosphate

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.4253368926666665

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.16885906953311

> <JCHEM_POLAR_SURFACE_AREA>
90.58000000000001

> <JCHEM_REFRACTIVITY>
64.69830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paraoxon

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013035
     RDKit          3D
Paraoxon
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.5060   -3.4698   -0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -2.1547    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -1.3092   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3837    0.1400    0.4313 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.5039    0.1584    1.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6376    1.4749   -0.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    2.4564    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298    3.6532   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750    0.3593    1.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.1473    0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -1.0779    0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218   -1.2977    0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.2788   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046   -0.4984   -0.7978 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.8023    0.4453   -1.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -1.7330   -0.6669 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2956    0.9552   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0116    1.1595    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6938   -3.6889   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5148   -3.5811   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4709   -4.3227    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -1.6642    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -2.3413    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213    2.0499    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    2.8057    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    3.3830   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210    4.2914   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5108    4.1941   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270   -1.8788    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144   -2.2590    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505    1.7362   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985    2.1456    0.0121 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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2  14   1  16  -1
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      27.970 -24.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.970 -23.397   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      26.636 -22.627   0.000  0.00  0.00           O+0
HETATM    4  P   UNK     0      26.636 -21.087   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      26.636 -19.547   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      28.176 -21.087   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      28.946 -22.419   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.486 -22.419   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      25.096 -21.087   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      24.326 -19.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.096 -18.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.326 -17.085   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.786 -17.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.016 -18.419   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.786 -19.753   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      22.016 -15.751   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0      22.786 -14.418   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      20.476 -15.751   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6    9                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0013035
HETATM    1  C1  UNL     1      -2.506  -3.470  -0.522  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.377  -2.155   0.164  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.452  -1.309  -0.413  1.00  0.00           O  
HETATM    4  P1  UNL     1      -1.384   0.140   0.431  1.00  0.00           P  
HETATM    5  O2  UNL     1      -2.504   0.158   1.477  1.00  0.00           O  
HETATM    6  O3  UNL     1      -1.638   1.475  -0.563  1.00  0.00           O  
HETATM    7  C3  UNL     1      -2.393   2.456   0.076  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.630   3.653  -0.794  1.00  0.00           C  
HETATM    9  O4  UNL     1       0.075   0.359   1.262  1.00  0.00           O  
HETATM   10  C5  UNL     1       1.328   0.147   0.759  1.00  0.00           C  
HETATM   11  C6  UNL     1       1.939  -1.078   0.865  1.00  0.00           C  
HETATM   12  C7  UNL     1       3.222  -1.298   0.352  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.897  -0.279  -0.273  1.00  0.00           C  
HETATM   14  N1  UNL     1       5.205  -0.498  -0.798  1.00  0.00           N1+
HETATM   15  O5  UNL     1       5.802   0.445  -1.364  1.00  0.00           O  
HETATM   16  O6  UNL     1       5.766  -1.733  -0.667  1.00  0.00           O1-
HETATM   17  C9  UNL     1       3.296   0.955  -0.386  1.00  0.00           C  
HETATM   18  C10 UNL     1       2.012   1.160   0.133  1.00  0.00           C  
HETATM   19  H1  UNL     1      -1.694  -3.689  -1.247  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.515  -3.581  -1.015  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.471  -4.323   0.215  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.391  -1.664   0.205  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.028  -2.341   1.219  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.321   2.050   0.535  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.765   2.806   0.947  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.831   3.383  -1.852  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.721   4.291  -0.759  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.511   4.194  -0.388  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.427  -1.879   1.348  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.714  -2.259   0.429  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.850   1.736  -0.882  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.598   2.146   0.012  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4
CONECT    4    5    5    6    9
CONECT    6    7
CONECT    7    8   24   25
CONECT    8   26   27   28
CONECT    9   10
CONECT   10   11   11   18
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   17
CONECT   14   15   15   16
CONECT   17   18   18   31
CONECT   18   32
END

HMDB0013035
     RDKit          3D
Paraoxon
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.5060   -3.4698   -0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -2.1547    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -1.3092   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3837    0.1400    0.4313 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.5039    0.1584    1.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6376    1.4749   -0.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    2.4564    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298    3.6532   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750    0.3593    1.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    0.1473    0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -1.0779    0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218   -1.2977    0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.2788   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046   -0.4984   -0.7978 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.8023    0.4453   -1.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -1.7330   -0.6669 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2956    0.9552   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0116    1.1595    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6938   -3.6889   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5148   -3.5811   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4709   -4.3227    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -1.6642    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -2.3413    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213    2.0499    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    2.8057    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    3.3830   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210    4.2914   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5108    4.1941   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4270   -1.8788    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144   -2.2590    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505    1.7362   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985    2.1456    0.0121 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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2  14   1  16  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Diethyl p-nitrophenyl phosphate	ChEBI
Diethyl paraoxon	ChEBI
Ethyl paraoxon	ChEBI
O,O-Diethyl O-p-nitrophenyl phosphate	ChEBI
p-Nitrophenyl diethyl phosphate	ChEBI
Phosphacol	ChEBI
Phosphoric acid diethyl 4-nitrophenyl ester	ChEBI
O,O-Diethyl-O-p-nitrophenylphosphoric acid	Kegg
Diethyl p-nitrophenyl phosphoric acid	Generator
O,O-Diethyl O-p-nitrophenyl phosphoric acid	Generator
p-Nitrophenyl diethyl phosphoric acid	Generator
Phosphate diethyl 4-nitrophenyl ester	Generator
O,O-Diethyl-O-p-nitrophenylphosphate	Generator
Diethyl P nitrophenyl phosphate	MeSH, HMDB
Phosphate, diethyl-P-nitrophenyl	MeSH, HMDB
Diethyl-P-nitrophenyl phosphate	MeSH, HMDB
Fosfakol	MeSH, HMDB

Chemical Formula

C₁₀H₁₄NO₆P

Average Molecular Weight

275.195

Monoisotopic Molecular Weight

275.055873697

IUPAC Name

diethyl 4-nitrophenyl phosphate

Traditional Name

paraoxon

CAS Registry Number

311-45-5

SMILES

CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

InChI Key

WYMSBXTXOHUIGT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

Alternative Parents

Substituents

Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organophosphate insecticide (CHEBI:27827 )
aryl dialkyl phosphate (CHEBI:27827 )
a small molecule (PARAOXON )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.64 mg/mL at 20 °C	Not Available
LogP	1.98	SANGSTER (1994)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.44 g/L	ALOGPS
logP	2.05	ALOGPS
logP	2.43	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-9.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	90.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	64.7 m³·mol⁻¹	ChemAxon
Polarizability	24.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.094	31661259
DarkChem	[M-H]-	161.365	31661259
DeepCCS	[M+H]+	152.879	30932474
DeepCCS	[M-H]-	149.619	30932474
DeepCCS	[M-2H]-	184.811	30932474
DeepCCS	[M+Na]+	161.083	30932474
AllCCS	[M+H]+	159.8	32859911
AllCCS	[M+H-H2O]+	156.4	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	164.0	32859911
AllCCS	[M-H]-	157.2	32859911
AllCCS	[M+Na-2H]-	157.3	32859911
AllCCS	[M+HCOO]-	157.5	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.	7.36 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4097 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.92 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2162.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	422.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	228.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	123.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	614.9 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	585.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	145.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1225.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	514.9 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	1339.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	393.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	471.4 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	58.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Paraoxon	CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O	2871.5	Standard polar	33892256
Paraoxon	CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O	1942.6	Standard non polar	33892256
Paraoxon	CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O	1908.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Paraoxon GC-EI-TOF (Non-derivatized)	splash10-0a4m-4910000000-9e80686be84777f12897	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Paraoxon GC-EI-TOF (Non-derivatized)	splash10-0a4m-4910000000-9e80686be84777f12897	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paraoxon GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-1490000000-49af8e137482487310cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paraoxon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-054k-9840000000-ed91d6d60187378e30e6	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 - Paraoxon 35V, Positive-QTOF	splash10-00di-1490000000-8d48b56d5d32ad4f5d91	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 10V, Positive-QTOF	splash10-004i-1290000000-6438528767f006512903	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 20V, Positive-QTOF	splash10-0gb9-0090000000-775108cc711fdc42be34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 40V, Positive-QTOF	splash10-004i-7900000000-0b2814cb44352b4577e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 10V, Negative-QTOF	splash10-00di-0190000000-cfd94300e89fae9a0128	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 20V, Negative-QTOF	splash10-00di-1490000000-609dc6a1aa30dd298795	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 40V, Negative-QTOF	splash10-00fr-2940000000-ab53630a454ec7edd2b2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 10V, Positive-QTOF	splash10-00dj-0090000000-4a26b1cf19be9be1c3a4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 20V, Positive-QTOF	splash10-00di-0090000000-e9fc319d73d2521066ba	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 40V, Positive-QTOF	splash10-0udi-3940000000-a73e447d3d81875336b5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 10V, Negative-QTOF	splash10-00e9-0090000000-d817a293e17ff8d661c9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 20V, Negative-QTOF	splash10-0002-0960000000-d7e8a3a00ae9564d521d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paraoxon 40V, Negative-QTOF	splash10-0pb9-2910000000-8234e0a0630a65f206b4	2021-09-25	Wishart Lab	View Spectrum

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

DB13495

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029261

KNApSAcK ID

Not Available

Chemspider ID

9026

KEGG Compound ID

C06606

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Paraoxon

METLIN ID

Not Available

PubChem Compound

9395

PDB ID

Not Available

ChEBI ID

27827

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

Enzymes

Enzyme Details

1. Serum paraoxonase/lactonase 3

General function:: Involved in arylesterase activity
Specific function:: Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:: PON3
Uniprot ID:: Q15166
Molecular weight:: 39607.185

Reactions

Paraoxon + Water → Diethylphosphate + 4-Nitrophenol	details

Enzyme Details

2. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

Reactions

Paraoxon + Water → Diethylphosphate + 4-Nitrophenol	details

Enzyme Details

3. Serum paraoxonase/arylesterase 2

General function:: Involved in arylesterase activity
Specific function:: Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:: PON2
Uniprot ID:: Q15165
Molecular weight:: 39380.535

Reactions

Paraoxon + Water → Diethylphosphate + 4-Nitrophenol	details

Showing metabocard for Paraoxon (HMDB0013035)

MOL for HMDB0013035 (Paraoxon)

3D MOL for HMDB0013035 (Paraoxon)

3D SDF for HMDB0013035 (Paraoxon)

3D-SDF for HMDB0013035 (Paraoxon)

PDB for HMDB0013035 (Paraoxon)

3D PDB for HMDB0013035 (Paraoxon)

SMILES for HMDB0013035 (Paraoxon)

INCHI for HMDB0013035 (Paraoxon)

Structure for HMDB0013035 (Paraoxon)

3D Structure for HMDB0013035 (Paraoxon)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions