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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2023-03-30 20:19:40 UTC

Update Date

2023-03-30 20:19:41 UTC

HMDB ID

HMDB0341503

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,2',3,4,4',5,5',6-Octachlorobiphenyl

Description

2,2',3,4,4',5,5',6-Octachlorobiphenyl 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. PCBs can also cause endocrine disurption by altering the production of thyroid hormones and binding to estrogen receptors, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. 2,2',3,4,4',5,5',6-Octachlorobiphenyl is possibly neutral. 2,2',3,4,4',5,5',6-Octachlorobiphenyl is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Only preventing further exposure and treating the observed symptoms can be done. However, PCBs do not break down readily and are still found in the environment. They were manufactured as commercial mixtures but banned in the 1970's because they were found to bioaccumulate and cause harmful health effects. They will bioaccumulate by binding to receptor proteins such as uteroglobin.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204292D          

 20 21  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
    2.1434   -2.8875    0.0000 Cl  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   -1.2375    0.0000 Cl  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
    2.1434   -3.7125    0.0000 Cl  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
    2.1434   -5.3625    0.0000 Cl  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
   -0.7145   -5.3625    0.0000 Cl  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  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 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  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341503

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H2Cl8/c13-4-2-6(15)5(14)1-3(4)7-8(16)10(18)12(20)11(19)9(7)17/h1-2H

> <INCHI_KEY>
DCPDZFRGNJDWPP-UHFFFAOYSA-N

> <FORMULA>
C12H2Cl8

> <MOLECULAR_WEIGHT>
429.768

> <EXACT_MASS>
425.76647172

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
35.16935435611329

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,3,4,5-pentachloro-6-(2,4,5-trichlorophenyl)benzene

> <ALOGPS_LOGP>
8.06

> <JCHEM_LOGP>
8.452828588666666

> <ALOGPS_LOGS>
-9.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
89.63259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.80e-07 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3,4,5-pentachloro-6-(2,4,5-trichlorophenyl)benzene

> <JCHEM_VEBER_RULE>
1

$$$$

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 Cl   UNK     0       4.001  -5.390   0.000  0.00  0.00          Cl+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      -1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       4.001  -6.930   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       4.001 -10.010   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       1.334 -11.550   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -1.334 -10.010   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11   19                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₂Cl₈

Average Molecular Weight

429.768

Monoisotopic Molecular Weight

425.76647172

IUPAC Name

1,2,3,4,5-pentachloro-6-(2,4,5-trichlorophenyl)benzene

Traditional Name

1,2,3,4,5-pentachloro-6-(2,4,5-trichlorophenyl)benzene

CAS Registry Number

Not Available

SMILES

ClC1=CC(Cl)=C(C=C1Cl)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl

InChI Identifier

InChI=1S/C12H2Cl8/c13-4-2-6(15)5(14)1-3(4)7-8(16)10(18)12(20)11(19)9(7)17/h1-2H

InChI Key

DCPDZFRGNJDWPP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Polychlorinated biphenyls

Alternative Parents

Substituents

Polychlorinated biphenyl
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Hydrocarbon derivative
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane ()

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	8.06	ALOGPS
logP	8.45	ChemAxon
logS	-9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.63 m³·mol⁻¹	ChemAxon
Polarizability	35.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,4,4',5,5',6-Octachlorobiphenyl 10V, Positive-QTOF	splash10-004i-0000900000-d0cbb71f1f0621526a05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,4,4',5,5',6-Octachlorobiphenyl 20V, Positive-QTOF	splash10-004i-0000900000-89bba32a2038863f2022	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,4,4',5,5',6-Octachlorobiphenyl 40V, Positive-QTOF	splash10-004i-0000900000-38c92d556ff8c3e5f96a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,4,4',5,5',6-Octachlorobiphenyl 10V, Negative-QTOF	splash10-00di-0000900000-709ab3d23b3eae406b5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,4,4',5,5',6-Octachlorobiphenyl 20V, Negative-QTOF	splash10-00di-0000900000-709ab3d23b3eae406b5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,4,4',5,5',6-Octachlorobiphenyl 40V, Negative-QTOF	splash10-00di-0011900000-ba5d5e6948331ee69de1	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

40483

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

Not Available

Showing metabocard for 2,2',3,4,4',5,5',6-Octachlorobiphenyl (HMDB0341503)

MOL for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

3D MOL for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

3D SDF for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

3D-SDF for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

PDB for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

3D PDB for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

SMILES for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

INCHI for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

Structure for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

3D Structure for HMDB0341503 (2,2',3,4,4',5,5',6-Octachlorobiphenyl)

Predicted Kovats Retention Indices

MS/MS Spectra