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Showing metabocard for 2,4,4'-Trichlorobiphenyl (HMDB0245472)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:32:17 UTC
Update Date2021-09-26 22:53:57 UTC
HMDB IDHMDB0245472
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,4,4'-Trichlorobiphenyl
Description2,4,4'-Trichlorobiphenyl, also known as PCB 28 or 2,4,4'-TCB, belongs to the class of organic compounds known as polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms attached to either benzene ring of the biphenyl moiety. 2,4,4'-Trichlorobiphenyl is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review very few articles have been published on 2,4,4'-Trichlorobiphenyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,4,4'-trichlorobiphenyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,4,4'-Trichlorobiphenyl 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

  Mrv0541 02241204232D          

 15 16  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 Cl  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
    1.4289   -1.6500    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
    0.7145   -2.8875    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   -1.6500    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
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3D MOL for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

HMDB0245472
     RDKit          3D
2,4,4'-Trichlorobiphenyl
 22 23  0  0  0  0  0  0  0  0999 V2000
   -5.2611   -0.1646    0.0010 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -0.0968   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717   -1.2642   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3941   -1.2354   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7190   -0.0269   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7364    0.0328   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320   -0.8467    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.8372    0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318    0.0426   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2957    0.0209   -0.0635 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8502    0.9235   -0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    0.9047   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868    2.0127   -1.9636 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636    1.1275   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568    1.1112    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2880   -2.2360   -0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841   -2.1251   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850   -1.5523    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -1.5319    1.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    1.6026   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9679    2.0854    0.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816    2.0533    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  2  0
 15  2  1  0
 12  6  1  0
  3 16  1  0
  4 17  1  0
  7 18  1  0
  8 19  1  0
 11 20  1  0
 14 21  1  0
 15 22  1  0
M  END
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3D SDF for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

  Mrv0541 02241204232D          

 15 16  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 Cl  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
    1.4289   -1.6500    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
    0.7145   -2.8875    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   -1.6500    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245472

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C(C=C1)C1=CC=C(Cl)C=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C12H7Cl3/c13-9-3-1-8(2-4-9)11-6-5-10(14)7-12(11)15/h1-7H

> <INCHI_KEY>
BZTYNSQSZHARAZ-UHFFFAOYSA-N

> <FORMULA>
C12H7Cl3

> <MOLECULAR_WEIGHT>
257.543

> <EXACT_MASS>
255.961333345

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
24.7571477117231

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dichloro-1-(4-chlorophenyl)benzene

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.432605207

> <ALOGPS_LOGS>
-6.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
65.60860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,4'-trichlorobiphenyl

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

HMDB0245472
     RDKit          3D
2,4,4'-Trichlorobiphenyl
 22 23  0  0  0  0  0  0  0  0999 V2000
   -5.2611   -0.1646    0.0010 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -0.0968   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717   -1.2642   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3941   -1.2354   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7190   -0.0269   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7364    0.0328   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320   -0.8467    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.8372    0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318    0.0426   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2957    0.0209   -0.0635 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8502    0.9235   -0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    0.9047   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868    2.0127   -1.9636 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636    1.1275   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568    1.1112    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2880   -2.2360   -0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841   -2.1251   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850   -1.5523    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -1.5319    1.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    1.6026   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9679    2.0854    0.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816    2.0533    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  2  0
 15  2  1  0
 12  6  1  0
  3 16  1  0
  4 17  1  0
  7 18  1  0
  8 19  1  0
 11 20  1  0
 14 21  1  0
 15 22  1  0
M  END
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PDB for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       1.334 -11.550   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
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3D PDB for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

COMPND    HMDB0245472
HETATM    1 CL1  UNL     1      -5.261  -0.165   0.001  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -3.509  -0.097  -0.044  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.772  -1.264  -0.148  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.394  -1.235  -0.185  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.719  -0.027  -0.119  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.736   0.033  -0.153  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.432  -0.847   0.659  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.814  -0.837   0.675  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.532   0.043  -0.114  1.00  0.00           C  
HETATM   10 CL2  UNL     1       5.296   0.021  -0.063  1.00  0.00          CL  
HETATM   11  C9  UNL     1       2.850   0.923  -0.927  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.462   0.905  -0.934  1.00  0.00           C  
HETATM   13 CL3  UNL     1       0.587   2.013  -1.964  1.00  0.00          CL  
HETATM   14  C11 UNL     1      -1.464   1.127  -0.016  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.857   1.111   0.023  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.288  -2.236  -0.202  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.784  -2.125  -0.266  1.00  0.00           H  
HETATM   18  H3  UNL     1       0.885  -1.552   1.292  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.373  -1.532   1.317  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.430   1.603  -1.535  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.968   2.085   0.040  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.382   2.053   0.105  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   15
CONECT    3    4   16
CONECT    4    5    5   17
CONECT    5    6   14
CONECT    6    7    7   12
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   10   11
CONECT   11   12   12   20
CONECT   12   13
CONECT   14   15   15   21
CONECT   15   22
END
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SMILES for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

ClC1=CC=C(C=C1)C1=CC=C(Cl)C=C1Cl
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INCHI for HMDB0245472 (2,4,4'-Trichlorobiphenyl)

InChI=1S/C12H7Cl3/c13-9-3-1-8(2-4-9)11-6-5-10(14)7-12(11)15/h1-7H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
PCB 28HMDB
2,4,4'-TCBHMDB
PCB-28HMDB
Chemical FormulaC12H7Cl3
Average Molecular Weight257.543
Monoisotopic Molecular Weight255.961333345
IUPAC Name2,4-dichloro-1-(4-chlorophenyl)benzene
Traditional Name2,4,4'-trichlorobiphenyl
CAS Registry NumberNot Available
SMILES
ClC1=CC=C(C=C1)C1=CC=C(Cl)C=C1Cl
InChI Identifier
InChI=1S/C12H7Cl3/c13-9-3-1-8(2-4-9)11-6-5-10(14)7-12(11)15/h1-7H
InChI KeyBZTYNSQSZHARAZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms attached to either benzene ring of the biphenyl moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentPolychlorinated biphenyls
Alternative Parents
Substituents
  • Polychlorinated biphenyl
  • 1,3-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.7ALOGPS
logP5.43ChemAxon
logS-6.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.61 m³·mol⁻¹ChemAxon
Polarizability24.76 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21924
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23448
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]