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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:04:52 UTC
Update Date2021-09-26 22:54:52 UTC
HMDB IDHMDB0246039
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,4,4',5-Tetrachlorobiphenyl
Description3,4,4',5-Tetrachlorobiphenyl, also known as PCB 81, 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. 3,4,4',5-Tetrachlorobiphenyl is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3,4,4',5-Tetrachlorobiphenyl 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 3,4,4',5-Tetrachlorobiphenyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,4,4',5-tetrachlorobiphenyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,4,4',5-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
Thumb
Synonyms
ValueSource
PCB 81Kegg
Chemical FormulaC12H6Cl4
Average Molecular Weight291.988
Monoisotopic Molecular Weight289.92236102
IUPAC Name1,2,3-trichloro-5-(4-chlorophenyl)benzene
Traditional Name1,2,3-trichloro-5-(4-chlorophenyl)benzene
CAS Registry NumberNot Available
SMILES
ClC1=CC=C(C=C1)C1=CC(Cl)=C(Cl)C(Cl)=C1
InChI Identifier
InChI=1S/C12H6Cl4/c13-9-3-1-7(2-4-9)8-5-10(14)12(16)11(15)6-8/h1-6H
InChI KeyBHWVLZJTVIYLIV-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
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
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
logP6.22ALOGPS
logP6.04ChemAxon
logS-6.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.41 m³·mol⁻¹ChemAxon
Polarizability27.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+162.99430932474
DeepCCS[M-H]-160.63630932474
DeepCCS[M-2H]-193.52230932474
DeepCCS[M+Na]+169.08730932474
AllCCS[M+H]+153.232859911
AllCCS[M+H-H2O]+149.432859911
AllCCS[M+NH4]+156.732859911
AllCCS[M+Na]+157.732859911
AllCCS[M-H]-133.332859911
AllCCS[M+Na-2H]-132.632859911
AllCCS[M+HCOO]-131.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4,4',5-TetrachlorobiphenylClC1=CC=C(C=C1)C1=CC(Cl)=C(Cl)C(Cl)=C12899.3Standard polar33892256
3,4,4',5-TetrachlorobiphenylClC1=CC=C(C=C1)C1=CC(Cl)=C(Cl)C(Cl)=C12076.1Standard non polar33892256
3,4,4',5-TetrachlorobiphenylClC1=CC=C(C=C1)C1=CC(Cl)=C(Cl)C(Cl)=C12153.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1090000000-71b0f69cd22ba4ce97b12021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-1390000000-63b522d85c9e735a407c2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 10V, Positive-QTOFsplash10-0006-0090000000-b7833a1319138d5e48662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 20V, Positive-QTOFsplash10-0006-0090000000-b7833a1319138d5e48662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 40V, Positive-QTOFsplash10-0006-0090000000-fc96746a2afa3ff69a212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 10V, Negative-QTOFsplash10-000i-0090000000-679ed448e368ff6506d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 20V, Negative-QTOFsplash10-000i-0090000000-679ed448e368ff6506d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 40V, Negative-QTOFsplash10-000i-0090000000-e45b83ce380727d876362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 10V, Negative-QTOFsplash10-000i-0090000000-a0109030c31ebbacd6ce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 20V, Negative-QTOFsplash10-000i-0090000000-a0109030c31ebbacd6ce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 40V, Negative-QTOFsplash10-000i-0090000000-b76e0447fd699176868d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 10V, Positive-QTOFsplash10-0006-0090000000-ebc4bc6a9154ade1216d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 20V, Positive-QTOFsplash10-0006-0090000000-ebc4bc6a9154ade1216d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,4',5-Tetrachlorobiphenyl 40V, Positive-QTOFsplash10-0006-0090000000-81a553a78069933848bf2021-10-12Wishart LabView Spectrum
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 ID46264
KEGG Compound IDC18114
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound51043
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 ]