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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:39:41 UTC

Update Date

2021-09-26 23:16:05 UTC

HMDB ID

HMDB0258870

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tetrachlorobisphenol A

Description

Tetrachlorobisphenol A, also known as tetrachlorodian, belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). Based on a literature review very few articles have been published on Tetrachlorobisphenol A. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tetrachlorobisphenol a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tetrachlorobisphenol A 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

HMDB0258870
     RDKit          3D
Tetrachlorobisphenol A
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0548   -2.2385   -1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -1.2690    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0564   -2.0555    1.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -0.3799    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    0.3618   -1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5549    1.2099   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813    2.1576   -2.6301 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064    1.3047   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5023    2.1208   -0.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1416    0.5566    0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    0.6389    2.3779 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -0.2868    1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -0.3950   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    0.4963    1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.3594    1.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361    2.4962    2.3704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3682    1.3216    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4738    2.1344   -0.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1790    0.4240   -1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    0.3703   -2.3394 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0947   -0.4261   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255   -2.7464   -1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.7272   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -2.9945   -1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631   -2.6357    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068   -2.7891    1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -1.4160    2.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785    0.2927   -1.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8033    2.7069   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.8778    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969    0.5634    1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269    2.8165    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9837   -1.0946   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 12  4  1  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 18 32  1  0
 21 33  1  0
M  END


  Mrv0541 05041413182D          

 21 22  0  0  0  0            999 V2000
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   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   -0.4125    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
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 Cl  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    1.2375    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
    0.7145   -4.5375    0.0000 O   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
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258870

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C1=CC(Cl)=C(O)C(Cl)=C1)C1=CC(Cl)=C(O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12Cl4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3

> <INCHI_KEY>
KYPYTERUKNKOLP-UHFFFAOYSA-N

> <FORMULA>
C15H12Cl4O2

> <MOLECULAR_WEIGHT>
366.067

> <EXACT_MASS>
363.959140456

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.18491549567456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dichloro-4-[2-(3,5-dichloro-4-hydroxyphenyl)propan-2-yl]phenol

> <ALOGPS_LOGP>
7.22

> <JCHEM_LOGP>
6.461154121333333

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.879507304058858

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.272342763102119

> <JCHEM_PKA_STRONGEST_BASIC>
-7.474943232383063

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
98.4943

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.03e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrachlorobisphenol A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258870
     RDKit          3D
Tetrachlorobisphenol A
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0548   -2.2385   -1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -1.2690    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0564   -2.0555    1.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -0.3799    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    0.3618   -1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5549    1.2099   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813    2.1576   -2.6301 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064    1.3047   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5023    2.1208   -0.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1416    0.5566    0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    0.6389    2.3779 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -0.2868    1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -0.3950   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    0.4963    1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.3594    1.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361    2.4962    2.3704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3682    1.3216    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4738    2.1344   -0.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1790    0.4240   -1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    0.3703   -2.3394 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0947   -0.4261   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255   -2.7464   -1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.7272   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -2.9945   -1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631   -2.6357    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068   -2.7891    1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -1.4160    2.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785    0.2927   -1.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8033    2.7069   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.8778    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969    0.5634    1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269    2.8165    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9837   -1.0946   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 12  4  1  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 18 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   18 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   19 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3    7    9                                                       
CONECT    4    7   10                                                       
CONECT    5    8   11                                                       
CONECT    6    8   12                                                       
CONECT    7    3    4   15                                                  
CONECT    8    5    6   15                                                  
CONECT    9    3   13   16                                                  
CONECT   10    4   13   17                                                  
CONECT   11    5   14   18                                                  
CONECT   12    6   14   19                                                  
CONECT   13    9   10   20                                                  
CONECT   14   11   12   21                                                  
CONECT   15    1    2    7    8                                             
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0258870
HETATM    1  C1  UNL     1      -0.055  -2.238  -1.111  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.005  -1.269   0.050  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.056  -2.056   1.319  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.192  -0.380   0.005  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.444   0.362  -1.122  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.555   1.210  -1.196  1.00  0.00           C  
HETATM    7 CL1  UNL     1      -2.881   2.158  -2.630  1.00  0.00          CL  
HETATM    8  C7  UNL     1      -3.406   1.305  -0.129  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.502   2.121  -0.160  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.142   0.557   0.993  1.00  0.00           C  
HETATM   11 CL2  UNL     1      -4.191   0.639   2.378  1.00  0.00          CL  
HETATM   12  C9  UNL     1      -2.040  -0.287   1.071  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.198  -0.395  -0.024  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.383   0.496   1.027  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.465   1.359   1.069  1.00  0.00           C  
HETATM   16 CL3  UNL     1       2.736   2.496   2.370  1.00  0.00          CL  
HETATM   17  C13 UNL     1       3.368   1.322   0.039  1.00  0.00           C  
HETATM   18  O2  UNL     1       4.474   2.134  -0.015  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.179   0.424  -1.016  1.00  0.00           C  
HETATM   20 CL4  UNL     1       4.333   0.370  -2.339  1.00  0.00          CL  
HETATM   21  C15 UNL     1       2.095  -0.426  -1.038  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.025  -2.746  -1.080  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.040  -1.727  -2.088  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.731  -2.994  -1.034  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.863  -2.636   1.523  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.907  -2.789   1.203  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.340  -1.416   2.178  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.779   0.293  -1.966  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.803   2.707  -0.900  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.827  -0.878   1.951  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.697   0.563   1.861  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.727   2.817   0.669  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.984  -1.095  -1.856  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4   13
CONECT    3   25   26   27
CONECT    4    5    5   12
CONECT    5    6   28
CONECT    6    7    8    8
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   12   12
CONECT   12   30
CONECT   13   14   14   21
CONECT   14   15   31
CONECT   15   16   17   17
CONECT   17   18   19
CONECT   18   32
CONECT   19   20   21   21
CONECT   21   33
END

HMDB0258870
     RDKit          3D
Tetrachlorobisphenol A
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0548   -2.2385   -1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -1.2690    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0564   -2.0555    1.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -0.3799    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    0.3618   -1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5549    1.2099   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813    2.1576   -2.6301 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064    1.3047   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5023    2.1208   -0.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1416    0.5566    0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    0.6389    2.3779 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -0.2868    1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -0.3950   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    0.4963    1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.3594    1.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361    2.4962    2.3704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3682    1.3216    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4738    2.1344   -0.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1790    0.4240   -1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    0.3703   -2.3394 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0947   -0.4261   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255   -2.7464   -1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.7272   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -2.9945   -1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631   -2.6357    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068   -2.7891    1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -1.4160    2.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785    0.2927   -1.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8033    2.7069   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.8778    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969    0.5634    1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269    2.8165    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9837   -1.0946   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 12  4  1  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 18 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3',5,5'-Tetrachlorobisphenol a	Kegg
Tetrachlorodian	Kegg
2,2-Bis(4-hydroxy-3,5-dichlorophenyl)propane	Kegg
4,4'-(1-Methylethylidene)bis(2,6-dichlorophenol)	MeSH
TCBPA CPD	MeSH

Chemical Formula

C₁₅H₁₂Cl₄O₂

Average Molecular Weight

366.067

Monoisotopic Molecular Weight

363.959140456

IUPAC Name

2,6-dichloro-4-[2-(3,5-dichloro-4-hydroxyphenyl)propan-2-yl]phenol

Traditional Name

tetrachlorobisphenol A

CAS Registry Number

Not Available

SMILES

CC(C)(C1=CC(Cl)=C(O)C(Cl)=C1)C1=CC(Cl)=C(O)C(Cl)=C1

InChI Identifier

InChI=1S/C15H12Cl4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3

InChI Key

KYPYTERUKNKOLP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Bisphenols

Alternative Parents

Substituents

Bisphenol
Phenylpropane
1,3-dichlorobenzene
2-halophenol
2-chlorophenol
Chlorobenzene
Halobenzene
Phenol
Aryl halide
Aryl chloride
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organohalogen compound
Organochloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

bisphenol (CHEBI:35004 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0258870)

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	7.22	ALOGPS
logP	6.46	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	6.27	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.49 m³·mol⁻¹	ChemAxon
Polarizability	34.18 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]+	181.201	30932474
DeepCCS	[M-H]-	178.843	30932474
DeepCCS	[M-2H]-	212.643	30932474
DeepCCS	[M+Na]+	187.87	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	154.2	32859911
AllCCS	[M+HCOO]-	153.4	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.	7.68 minutes	32390414
Predicted by Siyang on May 30, 2022	23.2209 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2907.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	804.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	309.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	564.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	569.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1121.9 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	1026.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	465.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1948.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	788.2 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	2146.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	765.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	648.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	706.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	534.3 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	129.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrachlorobisphenol A	CC(C)(C1=CC(Cl)=C(O)C(Cl)=C1)C1=CC(Cl)=C(O)C(Cl)=C1	4026.9	Standard polar	33892256
Tetrachlorobisphenol A	CC(C)(C1=CC(Cl)=C(O)C(Cl)=C1)C1=CC(Cl)=C(O)C(Cl)=C1	2700.6	Standard non polar	33892256
Tetrachlorobisphenol A	CC(C)(C1=CC(Cl)=C(O)C(Cl)=C1)C1=CC(Cl)=C(O)C(Cl)=C1	2620.7	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 - Tetrachlorobisphenol A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0129000000-d11faa3074c258e0bb4e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrachlorobisphenol A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrachlorobisphenol A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrachlorobisphenol A GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrachlorobisphenol A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrachlorobisphenol A GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-2419000000-f720422fd1ffc745c38f	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 - Tetrachlorobisphenol A 45V, Negative-QTOF	splash10-0w29-0092000000-17853fe903a3975e5f90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrachlorobisphenol A 60V, Negative-QTOF	splash10-0002-0090000000-2772dcd617aaa92b1f6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrachlorobisphenol A 30V, Negative-QTOF	splash10-03di-0019000000-ba2de1df5989b335615e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrachlorobisphenol A 15V, Negative-QTOF	splash10-03di-0009000000-f35b14b05fa85968fee8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrachlorobisphenol A 75V, Negative-QTOF	splash10-001j-0190000000-04aba6d56eb8a7f85072	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrachlorobisphenol A 90V, Negative-QTOF	splash10-001i-1190000000-700b9d5cef5b6b06d83e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrachlorobisphenol A 45V, Positive-QTOF	splash10-0w29-0092000000-51a18251a74cd7430645	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrachlorobisphenol A 10V, Positive-QTOF	splash10-03di-0009000000-05964ea61258d00fd8ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrachlorobisphenol A 20V, Positive-QTOF	splash10-03di-0009000000-6ac1db351cc0fded9281	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrachlorobisphenol A 40V, Positive-QTOF	splash10-0hha-0439000000-94f5c9202b1187d29d99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrachlorobisphenol A 10V, Negative-QTOF	splash10-03di-0009000000-94363d558a1a5e2576b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrachlorobisphenol A 20V, Negative-QTOF	splash10-03di-0009000000-caeb72dcd7861497e33d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrachlorobisphenol A 40V, Negative-QTOF	splash10-03di-0719000000-05ef1cc3f3e40642b2ef	2016-08-03	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

6367

KEGG Compound ID

C14528

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 ]

Showing metabocard for Tetrachlorobisphenol A (HMDB0258870)

MOL for HMDB0258870 (Tetrachlorobisphenol A)

3D MOL for HMDB0258870 (Tetrachlorobisphenol A)

3D SDF for HMDB0258870 (Tetrachlorobisphenol A)

3D-SDF for HMDB0258870 (Tetrachlorobisphenol A)

PDB for HMDB0258870 (Tetrachlorobisphenol A)

3D PDB for HMDB0258870 (Tetrachlorobisphenol A)

SMILES for HMDB0258870 (Tetrachlorobisphenol A)

INCHI for HMDB0258870 (Tetrachlorobisphenol A)

Structure for HMDB0258870 (Tetrachlorobisphenol A)

3D Structure for HMDB0258870 (Tetrachlorobisphenol A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra