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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:51:28 UTC

Update Date

2021-09-26 22:52:39 UTC

HMDB ID

HMDB0244717

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,2',6,6'-Tetrachlorobiphenyl

Description

2,2',6,6'-Tetrachlorobiphenyl, also known as 2,2',6,6'-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. 2,2',6,6'-Tetrachlorobiphenyl is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on 2,2',6,6'-Tetrachlorobiphenyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,2',6,6'-tetrachlorobiphenyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,2',6,6'-Tetrachlorobiphenyl 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


  Mrv0541 02241204242D          

 16 17  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
   -0.7145   -2.8875    0.0000 Cl  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 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 Cl  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
   -2.1434   -0.4125    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244717

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=CC(Cl)=C1C1=C(Cl)C=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C12H6Cl4/c13-7-3-1-4-8(14)11(7)12-9(15)5-2-6-10(12)16/h1-6H

> <INCHI_KEY>
PXAGFNRKXSYIHU-UHFFFAOYSA-N

> <FORMULA>
C12H6Cl4

> <MOLECULAR_WEIGHT>
291.988

> <EXACT_MASS>
289.92236102

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.7694928087356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dichloro-2-(2,6-dichlorophenyl)benzene

> <ALOGPS_LOGP>
6.22

> <JCHEM_LOGP>
6.036649883333333

> <ALOGPS_LOGS>
-6.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
70.4134

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2',6,6'-tetrachlorobiphenyl

> <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  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 Cl   UNK     0      -1.334  -5.390   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -2.667  -4.620   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   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
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2',6,6'-TCB	HMDB
262'6'-Tetrachloro-biphenyl(26TCB)	HMDB
262'6'-Tetrachloro-biphenyl	HMDB

Chemical Formula

C₁₂H₆Cl₄

Average Molecular Weight

291.988

Monoisotopic Molecular Weight

289.92236102

IUPAC Name

1,3-dichloro-2-(2,6-dichlorophenyl)benzene

Traditional Name

2,2',6,6'-tetrachlorobiphenyl

CAS Registry Number

Not Available

SMILES

ClC1=CC=CC(Cl)=C1C1=C(Cl)C=CC=C1Cl

InChI Identifier

InChI=1S/C12H6Cl4/c13-7-3-1-4-8(14)11(7)12-9(15)5-2-6-10(12)16/h1-6H

InChI Key

PXAGFNRKXSYIHU-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
1,3-dichlorobenzene
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0244717)

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	6.22	ALOGPS
logP	6.04	ChemAxon
logS	-6.9	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	70.41 m³·mol⁻¹	ChemAxon
Polarizability	25.77 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 Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	153.032	30932474
DeepCCS	[M-H]-	150.674	30932474
DeepCCS	[M-2H]-	183.895	30932474
DeepCCS	[M+Na]+	159.125	30932474
AllCCS	[M+H]+	151.5	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	155.1	32859911
AllCCS	[M+Na]+	156.1	32859911
AllCCS	[M-H]-	126.7	32859911
AllCCS	[M+Na-2H]-	125.8	32859911
AllCCS	[M+HCOO]-	124.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,2',6,6'-Tetrachlorobiphenyl	ClC1=CC=CC(Cl)=C1C1=C(Cl)C=CC=C1Cl	2673.8	Standard polar	33892256
2,2',6,6'-Tetrachlorobiphenyl	ClC1=CC=CC(Cl)=C1C1=C(Cl)C=CC=C1Cl	1786.5	Standard non polar	33892256
2,2',6,6'-Tetrachlorobiphenyl	ClC1=CC=CC(Cl)=C1C1=C(Cl)C=CC=C1Cl	1806.9	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 - 2,2',6,6'-Tetrachlorobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1090000000-058677160c9f3240258c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-5690000000-5e204e2c65fbdea7f379	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 10V, Positive-QTOF	splash10-0006-0090000000-406fba0954ebc58742ee	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 20V, Positive-QTOF	splash10-0006-0090000000-535f97e3ce7b64dbad66	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 40V, Positive-QTOF	splash10-0udl-0090000000-08decca38f44e7fbe3a0	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 10V, Negative-QTOF	splash10-000i-0090000000-8a90002d52484d0346e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 20V, Negative-QTOF	splash10-000i-0090000000-da7b1ec4a0e47919326c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 40V, Negative-QTOF	splash10-0udr-0090000000-3d917299e6fd60c1ec23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 10V, Positive-QTOF	splash10-0006-0090000000-ebc4bc6a9154ade1216d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 20V, Positive-QTOF	splash10-0006-0090000000-ebc4bc6a9154ade1216d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 40V, Positive-QTOF	splash10-0006-0090000000-ebc4bc6a9154ade1216d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 10V, Negative-QTOF	splash10-000i-0090000000-a0109030c31ebbacd6ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 20V, Negative-QTOF	splash10-000i-0090000000-a0109030c31ebbacd6ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',6,6'-Tetrachlorobiphenyl 40V, Negative-QTOF	splash10-0019-4090000000-74e7693467ce9227e36c	2021-10-12	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

25677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

27588

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 2,2',6,6'-Tetrachlorobiphenyl (HMDB0244717)

MOL for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

3D MOL for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

3D SDF for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

3D-SDF for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

PDB for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

3D PDB for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

SMILES for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

INCHI for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

Structure for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

3D Structure for HMDB0244717 (2,2',6,6'-Tetrachlorobiphenyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra