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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2023-03-30 19:45:20 UTC

Update Date

2023-03-30 19:45:20 UTC

HMDB ID

HMDB0341499

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,3,3',4',6-Pentachlorobiphenyl

Description

2,3,3',4,6-Pentachlorobiphenyl 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',4,6-Pentachlorobiphenyl is possibly neutral. 2,3,3',4,6-Pentachlorobiphenyl is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. PCBs are a group of synthetic organic compounds with 1-10 chlorine atoms attached to biphenyl. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. Acute inhalation can be treated by administering oxygen. However, PCBs do not break down readily and are still found in the environment. They will bioaccumulate by binding to receptor proteins such as uteroglobin.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204262D          

 17 18  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   -2.8875    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
    0.0000   -4.1250    0.0000 Cl  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    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 Cl  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
   -1.4289   -1.6500    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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341499

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H5Cl5/c13-7-3-1-2-6(4-7)10-8(14)5-9(15)11(16)12(10)17/h1-5H

> <INCHI_KEY>
XGQBSVVYMVILEL-UHFFFAOYSA-N

> <FORMULA>
C12H5Cl5

> <MOLECULAR_WEIGHT>
326.433

> <EXACT_MASS>
323.883388695

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
28.79792491095255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.77

> <JCHEM_LOGP>
6.640694559666667

> <ALOGPS_LOGS>
-7.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
75.2182

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.12e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3,5-tetrachloro-4-(3-chlorophenyl)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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       0.000  -7.700   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -5.335  -7.700   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -5.335  -4.620   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -2.667  -3.080   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                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   16                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₅Cl₅

Average Molecular Weight

326.433

Monoisotopic Molecular Weight

323.883388695

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H5Cl5/c13-7-3-1-2-6(4-7)10-8(14)5-9(15)11(16)12(10)17/h1-5H

InChI Key

XGQBSVVYMVILEL-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	6.77	ALOGPS
logP	6.64	ChemAxon
logS	-7.7	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	75.22 m³·mol⁻¹	ChemAxon
Polarizability	28.8 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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
MS	Mass Spectrum (Electron Ionization)	splash10-004i-4957000000-385f792bb37f737bd9cd	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',6-Pentachlorobiphenyl 10V, Positive-QTOF	splash10-00di-0009000000-d1be61368b849b3fbf1c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4',6-Pentachlorobiphenyl 20V, Positive-QTOF	splash10-00di-0009000000-d1be61368b849b3fbf1c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4',6-Pentachlorobiphenyl 40V, Positive-QTOF	splash10-00di-1069000000-fdc27c1794331b5fdfce	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4',6-Pentachlorobiphenyl 10V, Negative-QTOF	splash10-00di-0009000000-ca8d0524448ae22567d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4',6-Pentachlorobiphenyl 20V, Negative-QTOF	splash10-00di-0009000000-ca8d0524448ae22567d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,3',4',6-Pentachlorobiphenyl 40V, Negative-QTOF	splash10-00di-0049000000-ace37da4c54d44fd661c	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

93440

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 2,3,3',4',6-Pentachlorobiphenyl (HMDB0341499)

MOL for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

3D MOL for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

3D SDF for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

3D-SDF for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

PDB for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

3D PDB for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

SMILES for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

INCHI for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

Structure for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

3D Structure for HMDB0341499 (2,3,3',4',6-Pentachlorobiphenyl)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra