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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2023-03-30 20:36:37 UTC

Update Date

2023-03-30 20:36:37 UTC

HMDB ID

HMDB0341505

Secondary Accession Numbers

None

Metabolite Identification

Common Name

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

Description

2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl 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',3,3',4,4',5,5',6-Nonachlorobiphenyl is possibly neutral. 2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. They were manufactured as commercial mixtures but banned in the 1970's because they were found to bioaccumulate and cause harmful health effects. The most common health effects of PCBs are skin conditions such as chloracne and rashes. They will bioaccumulate by binding to receptor proteins such as uteroglobin. 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.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204302D          

 21 22  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
    0.7145   -3.7125    0.0000 Cl  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
    2.8579   -1.6500    0.0000 Cl  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341505

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12HCl9/c13-3-1-2(5(14)9(18)6(3)15)4-7(16)10(19)12(21)11(20)8(4)17/h1H

> <INCHI_KEY>
JFIMDKGRGPNPRQ-UHFFFAOYSA-N

> <FORMULA>
C12HCl9

> <MOLECULAR_WEIGHT>
464.213

> <EXACT_MASS>
459.727499395

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
37.27709985712882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
8.25

> <JCHEM_LOGP>
9.056873265

> <ALOGPS_LOGS>
-9.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
94.43739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-07 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nonachloro-1,1'-biphenyl

> <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 Cl   UNK     0       1.334  -6.930   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      -1.334  -5.390   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       5.335  -3.080   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       8.002  -4.620   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       8.002  -7.700   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       5.335  -9.240   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       2.667  -7.700   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9                                                            
CONECT   11    4   12   20                                                  
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   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂HCl₉

Average Molecular Weight

464.213

Monoisotopic Molecular Weight

459.727499395

IUPAC Name

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

Traditional Name

nonachloro-1,1'-biphenyl

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12HCl9/c13-3-1-2(5(14)9(18)6(3)15)4-7(16)10(19)12(21)11(20)8(4)17/h1H

InChI Key

JFIMDKGRGPNPRQ-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	8.25	ALOGPS
logP	9.06	ChemAxon
logS	-9.2	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	94.44 m³·mol⁻¹	ChemAxon
Polarizability	37.28 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)	splash10-03xu-0215900000-847ca3c1747c57784e9e	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',3,3',4,4',5,5',6-Nonachlorobiphenyl 10V, Positive-QTOF	splash10-03di-0000900000-db32b142751346ddfa33	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl 20V, Positive-QTOF	splash10-03di-0000900000-db32b142751346ddfa33	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl 40V, Positive-QTOF	splash10-03di-0000900000-76fd4cf0ae5ffbc55e5b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl 10V, Negative-QTOF	splash10-0a4i-0000900000-dadec25129c2229de914	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl 20V, Negative-QTOF	splash10-0a4i-0000900000-dadec25129c2229de914	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl 40V, Negative-QTOF	splash10-0a4i-0000900000-1dcd93d5b462ca04e246	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

38411

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',3,3',4,4',5,5',6-Nonachlorobiphenyl (HMDB0341505)

MOL for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

3D MOL for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

3D SDF for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

3D-SDF for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

PDB for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

3D PDB for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

SMILES for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

INCHI for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

Structure for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

3D Structure for HMDB0341505 (2,2',3,3',4,4',5,5',6-Nonachlorobiphenyl)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra