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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:29:25 UTC

Update Date

2021-09-26 22:53:53 UTC

HMDB ID

HMDB0245419

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,3,3',4,4',5,5'-Heptachlorobiphenyl

Description

2,3,3',4,4',5,5'-Heptachlorobiphenyl, also known as heptachlorobiphenyl or PCB 189, 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. 2,3,3',4,4',5,5'-Heptachlorobiphenyl is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2,3,3',4,4',5,5'-Heptachlorobiphenyl 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 2,3,3',4,4',5,5'-Heptachlorobiphenyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3,3',4,4',5,5'-heptachlorobiphenyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3,3',4,4',5,5'-Heptachlorobiphenyl 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 02241204292D          

 19 20  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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245419

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H3Cl7/c13-6-1-4(2-7(14)10(6)17)5-3-8(15)11(18)12(19)9(5)16/h1-3H

> <INCHI_KEY>
XUAWBXBYHDRROL-UHFFFAOYSA-N

> <FORMULA>
C12H3Cl7

> <MOLECULAR_WEIGHT>
395.323

> <EXACT_MASS>
391.805444045

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
33.49508692735749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.69

> <JCHEM_LOGP>
7.848783912333333

> <ALOGPS_LOGS>
-8.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
84.8278

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.72e-07 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3,4-tetrachloro-5-(3,4,5-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  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 Cl   UNK     0      -1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       8.002  -4.620   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       8.002  -7.700   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       5.335  -9.240   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       2.667  -7.700   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8                                                            
CONECT   10    4   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PCB 189	Kegg
Heptachlorobiphenyl	HMDB
2,3,4,5,3',4',5'-Heptachlorobiphenyl	HMDB

Chemical Formula

C₁₂H₃Cl₇

Average Molecular Weight

395.323

Monoisotopic Molecular Weight

391.805444045

IUPAC Name

1,2,3,4-tetrachloro-5-(3,4,5-trichlorophenyl)benzene

Traditional Name

1,2,3,4-tetrachloro-5-(3,4,5-trichlorophenyl)benzene

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H3Cl7/c13-6-1-4(2-7(14)10(6)17)5-3-8(15)11(18)12(19)9(5)16/h1-3H

InChI Key

XUAWBXBYHDRROL-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

trichlorobenzene (CHEBI:81525 )
tetrachlorobenzene (CHEBI:81525 )
heptachlorobiphenyl (CHEBI:81525 )
Mono-ortho PCBs (C18123 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0245419)

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	7.69	ALOGPS
logP	7.85	ChemAxon
logS	-8.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.83 m³·mol⁻¹	ChemAxon
Polarizability	33.5 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]+	167.487	30932474
DeepCCS	[M-H]-	165.129	30932474
DeepCCS	[M-2H]-	198.312	30932474
DeepCCS	[M+Na]+	173.581	30932474
AllCCS	[M+H]+	164.7	32859911
AllCCS	[M+H-H2O]+	161.7	32859911
AllCCS	[M+NH4]+	167.5	32859911
AllCCS	[M+Na]+	168.3	32859911
AllCCS	[M-H]-	106.2	32859911
AllCCS	[M+Na-2H]-	104.7	32859911
AllCCS	[M+HCOO]-	103.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3,3',4,4',5,5'-Heptachlorobiphenyl	ClC1=CC(=CC(Cl)=C1Cl)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl	3351.2	Standard polar	33892256
2,3,3',4,4',5,5'-Heptachlorobiphenyl	ClC1=CC(=CC(Cl)=C1Cl)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl	2541.5	Standard non polar	33892256
2,3,3',4,4',5,5'-Heptachlorobiphenyl	ClC1=CC(=CC(Cl)=C1Cl)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl	2614.8	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 - 2,3,3',4,4',5,5'-Heptachlorobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-1029000000-64269e503f80420ee272	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006w-1629000000-d4f021ba668cdc064b2e	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 - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 10V, Positive-QTOF	splash10-0006-0009000000-e96a695aca481bc1479f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 20V, Positive-QTOF	splash10-0006-0009000000-e96a695aca481bc1479f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 40V, Positive-QTOF	splash10-0006-0009000000-32311116a46f7d492b68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 10V, Negative-QTOF	splash10-0006-0009000000-48d3287ab555668befe2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 20V, Negative-QTOF	splash10-0006-0009000000-48d3287ab555668befe2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 40V, Negative-QTOF	splash10-0006-0009000000-d58a901544e2ba0b1adc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 10V, Positive-QTOF	splash10-0006-0009000000-5227f1668754f1c63530	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 20V, Positive-QTOF	splash10-0006-0009000000-5227f1668754f1c63530	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 40V, Positive-QTOF	splash10-0006-0009000000-5227f1668754f1c63530	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 10V, Negative-QTOF	splash10-0006-0009000000-fbc44457b0cf102a6f48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 20V, Negative-QTOF	splash10-0006-0009000000-fbc44457b0cf102a6f48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4,4',5,5'-Heptachlorobiphenyl 40V, Negative-QTOF	splash10-0006-0009000000-fbc44457b0cf102a6f48	2021-10-12	Wishart Lab	View Spectrum

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

35108

KEGG Compound ID

C18123

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38306

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 2,3,3',4,4',5,5'-Heptachlorobiphenyl (HMDB0245419)

MOL for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

3D MOL for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

3D SDF for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

3D-SDF for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

PDB for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

3D PDB for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

SMILES for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

INCHI for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

Structure for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

3D Structure for HMDB0245419 (2,3,3',4,4',5,5'-Heptachlorobiphenyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra