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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:45:20 UTC

Update Date

2021-09-26 22:59:59 UTC

HMDB ID

HMDB0249250

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bis(2,4,6-trichlorophenyl) oxalate

Description

bis(2,4,6-trichlorophenyl) oxalate belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative. bis(2,4,6-trichlorophenyl) oxalate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Bis(2,4,6-trichlorophenyl) oxalate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bis(2,4,6-trichlorophenyl) oxalate 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

HMDB0249250
     RDKit          3D
Bis(2,4,6-trichlorophenyl) oxalate
 28 29  0  0  0  0  0  0  0  0999 V2000
    0.9481    0.7879   -1.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832    0.1895   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -0.2281    0.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0403   -0.0331    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7190    1.0899    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    2.3482    1.4113 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0647    1.2481    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7380    0.2814   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4268    0.4673   -0.8718 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0720   -0.8359   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173   -0.9986   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.4596   -1.1910 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -0.0670   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157   -0.6585    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622    0.3469   -0.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    0.1042   -0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857   -1.0574   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7640   -2.1958   -1.8835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -1.3139   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7067   -0.3986    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3677   -0.6990    0.6571 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880    0.7697    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572    1.0217    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    2.5287    0.7567 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6008    2.1309    0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5954   -1.6090   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4957   -2.2323   -0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6580    1.4724    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 11  4  1  0
 23 16  1  0
  7 25  1  0
 10 26  1  0
 19 27  1  0
 22 28  1  0
M  END


  Mrv1533004241519522D          

 24 25  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 15 22  1  0  0  0  0
  4 23  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249250

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC(Cl)=C(OC(=O)C(=O)OC2=C(Cl)C=C(Cl)C=C2Cl)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H4Cl6O4/c15-5-1-7(17)11(8(18)2-5)23-13(21)14(22)24-12-9(19)3-6(16)4-10(12)20/h1-4H

> <INCHI_KEY>
GEVPIWPYWJZSPR-UHFFFAOYSA-N

> <FORMULA>
C14H4Cl6O4

> <MOLECULAR_WEIGHT>
448.88

> <EXACT_MASS>
445.8240748

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
37.58665884761943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
bis(2,4,6-trichlorophenyl) oxalate

> <ALOGPS_LOGP>
6.51

> <JCHEM_LOGP>
7.434888164666667

> <ALOGPS_LOGS>
-8.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.147212342209112

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
92.36079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
TCPO

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249250
     RDKit          3D
Bis(2,4,6-trichlorophenyl) oxalate
 28 29  0  0  0  0  0  0  0  0999 V2000
    0.9481    0.7879   -1.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832    0.1895   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -0.2281    0.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0403   -0.0331    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7190    1.0899    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    2.3482    1.4113 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0647    1.2481    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7380    0.2814   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4268    0.4673   -0.8718 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0720   -0.8359   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173   -0.9986   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.4596   -1.1910 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -0.0670   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157   -0.6585    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622    0.3469   -0.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    0.1042   -0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857   -1.0574   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7640   -2.1958   -1.8835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -1.3139   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7067   -0.3986    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3677   -0.6990    0.6571 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880    0.7697    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572    1.0217    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    2.5287    0.7567 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6008    2.1309    0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5954   -1.6090   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4957   -2.2323   -0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6580    1.4724    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 11  4  1  0
 23 16  1  0
  7 25  1  0
 10 26  1  0
 19 27  1  0
 22 28  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       5.335  -6.160   0.000  0.00  0.00          Cl+0
HETATM   21 Cl   UNK     0       8.002  -1.540   0.000  0.00  0.00          Cl+0
HETATM   22 Cl   UNK     0       2.667  -1.540   0.000  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0      -4.001  -2.310   0.000  0.00  0.00          Cl+0
HETATM   24 Cl   UNK     0      -6.668  -6.930   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   17                                                            
CONECT   22   15                                                            
CONECT   23    4                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0249250
HETATM    1  O1  UNL     1       0.948   0.788  -1.535  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.683   0.189  -0.461  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.696  -0.228   0.362  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.040  -0.033   0.090  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.719   1.090   0.505  1.00  0.00           C  
HETATM    6 CL1  UNL     1       2.909   2.348   1.411  1.00  0.00          CL  
HETATM    7  C4  UNL     1       5.065   1.248   0.213  1.00  0.00           C  
HETATM    8  C5  UNL     1       5.738   0.281  -0.498  1.00  0.00           C  
HETATM    9 CL2  UNL     1       7.427   0.467  -0.872  1.00  0.00          CL  
HETATM   10  C6  UNL     1       5.072  -0.836  -0.913  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.717  -0.999  -0.621  1.00  0.00           C  
HETATM   12 CL3  UNL     1       2.942  -2.460  -1.191  1.00  0.00          CL  
HETATM   13  C8  UNL     1      -0.723  -0.067  -0.080  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.016  -0.659   0.979  1.00  0.00           O  
HETATM   15  O4  UNL     1      -1.762   0.347  -0.898  1.00  0.00           O  
HETATM   16  C9  UNL     1      -3.065   0.104  -0.537  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.686  -1.057  -0.925  1.00  0.00           C  
HETATM   18 CL4  UNL     1      -2.764  -2.196  -1.884  1.00  0.00          CL  
HETATM   19  C11 UNL     1      -5.017  -1.314  -0.560  1.00  0.00           C  
HETATM   20  C12 UNL     1      -5.707  -0.399   0.191  1.00  0.00           C  
HETATM   21 CL5  UNL     1      -7.368  -0.699   0.657  1.00  0.00          CL  
HETATM   22  C13 UNL     1      -5.088   0.770   0.584  1.00  0.00           C  
HETATM   23  C14 UNL     1      -3.757   1.022   0.217  1.00  0.00           C  
HETATM   24 CL6  UNL     1      -3.048   2.529   0.757  1.00  0.00          CL  
HETATM   25  H1  UNL     1       5.601   2.131   0.538  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.595  -1.609  -1.477  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.496  -2.232  -0.872  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.658   1.472   1.176  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4
CONECT    4    5    5   11
CONECT    5    6    7
CONECT    7    8    8   25
CONECT    8    9   10
CONECT   10   11   11   26
CONECT   11   12
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17   17   23
CONECT   17   18   19
CONECT   19   20   20   27
CONECT   20   21   22
CONECT   22   23   23   28
CONECT   23   24
END

HMDB0249250
     RDKit          3D
Bis(2,4,6-trichlorophenyl) oxalate
 28 29  0  0  0  0  0  0  0  0999 V2000
    0.9481    0.7879   -1.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832    0.1895   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -0.2281    0.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0403   -0.0331    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7190    1.0899    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9094    2.3482    1.4113 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0647    1.2481    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7380    0.2814   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4268    0.4673   -0.8718 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0720   -0.8359   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173   -0.9986   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.4596   -1.1910 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226   -0.0670   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157   -0.6585    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622    0.3469   -0.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    0.1042   -0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857   -1.0574   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7640   -2.1958   -1.8835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -1.3139   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7067   -0.3986    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3677   -0.6990    0.6571 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880    0.7697    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572    1.0217    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    2.5287    0.7567 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6008    2.1309    0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5954   -1.6090   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4957   -2.2323   -0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6580    1.4724    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 11  4  1  0
 23 16  1  0
  7 25  1  0
 10 26  1  0
 19 27  1  0
 22 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bis(2,4,6-trichlorophenyl) oxalic acid	Generator
Bis-tcpo	MeSH
Bis(2,4,6-trichlorophenyl)oxalate	MeSH

Chemical Formula

C₁₄H₄Cl₆O₄

Average Molecular Weight

448.88

Monoisotopic Molecular Weight

445.8240748

IUPAC Name

bis(2,4,6-trichlorophenyl) oxalate

Traditional Name

TCPO

CAS Registry Number

Not Available

SMILES

ClC1=CC(Cl)=C(OC(=O)C(=O)OC2=C(Cl)C=C(Cl)C=C2Cl)C(Cl)=C1

InChI Identifier

InChI=1S/C14H4Cl6O4/c15-5-1-7(17)11(8(18)2-5)23-13(21)14(22)24-12-9(19)3-6(16)4-10(12)20/h1-4H

InChI Key

GEVPIWPYWJZSPR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Phenol ester
Phenoxy compound
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organochloride
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	6.51	ALOGPS
logP	7.43	ChemAxon
logS	-8.3	ALOGPS
pKa (Strongest Basic)	-8.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	92.36 m³·mol⁻¹	ChemAxon
Polarizability	37.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	187.09	30932474
DeepCCS	[M-H]-	184.732	30932474
DeepCCS	[M-2H]-	218.602	30932474
DeepCCS	[M+Na]+	193.83	30932474
AllCCS	[M+H]+	176.6	32859911
AllCCS	[M+H-H2O]+	174.2	32859911
AllCCS	[M+NH4]+	178.9	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	117.3	32859911
AllCCS	[M+Na-2H]-	115.3	32859911
AllCCS	[M+HCOO]-	113.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	23.8122 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2848.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	865.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	325.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	642.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	513.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1099.2 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	1137.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	648.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1997.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	935.1 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	2277.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	813.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	599.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	968.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	542.4 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	253.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bis(2,4,6-trichlorophenyl) oxalate	ClC1=CC(Cl)=C(OC(=O)C(=O)OC2=C(Cl)C=C(Cl)C=C2Cl)C(Cl)=C1	3661.8	Standard polar	33892256
Bis(2,4,6-trichlorophenyl) oxalate	ClC1=CC(Cl)=C(OC(=O)C(=O)OC2=C(Cl)C=C(Cl)C=C2Cl)C(Cl)=C1	2807.8	Standard non polar	33892256
Bis(2,4,6-trichlorophenyl) oxalate	ClC1=CC(Cl)=C(OC(=O)C(=O)OC2=C(Cl)C=C(Cl)C=C2Cl)C(Cl)=C1	2757.0	Semi standard non polar	33892256

Spectra

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160567

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

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3D PDB for HMDB0249250 (Bis(2,4,6-trichlorophenyl) oxalate)

SMILES for HMDB0249250 (Bis(2,4,6-trichlorophenyl) oxalate)

INCHI for HMDB0249250 (Bis(2,4,6-trichlorophenyl) oxalate)

Structure for HMDB0249250 (Bis(2,4,6-trichlorophenyl) oxalate)

3D Structure for HMDB0249250 (Bis(2,4,6-trichlorophenyl) oxalate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized