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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2023-03-30 19:11:15 UTC

Update Date

2023-03-30 19:11:15 UTC

HMDB ID

HMDB0341495

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,2’,4,4’,5,5’-Hexabromobiphenyl

Description

2,2',4,4',5,5'-Hexabromobiphenyl, also known as PBB 153, belongs to the class of organic compounds known as polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom. Symptoms of PBB exposure may include nausea, abdominal pain, loss of appetite, joint pain, fatigue, and weakness. 2,2',4,4',5,5'-Hexabromobiphenyl is possibly neutral. 2,2',4,4',5,5'-Hexabromobiphenyl is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. 2,2',4,4',5,5'-Hexabromobiphenyl is a polybrominated biphenyl. Seek immediate medical advice. They can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204092D          

 18 19  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 Br  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
    2.1434   -2.8875    0.0000 Br  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   -1.2375    0.0000 Br  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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 Br  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  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 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  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341495

> <DATABASE_NAME>
hmdb

> <SMILES>
BrC1=CC(Br)=C(C=C1Br)C1=CC(Br)=C(Br)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C12H4Br6/c13-7-3-11(17)9(15)1-5(7)6-2-10(16)12(18)4-8(6)14/h1-4H

> <INCHI_KEY>
HMBBJSKXDBUNNT-UHFFFAOYSA-N

> <FORMULA>
C12H4Br6

> <MOLECULAR_WEIGHT>
627.584

> <EXACT_MASS>
621.54132601

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
38.15996695250957

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,4-tribromo-5-(2,4,5-tribromophenyl)benzene

> <ALOGPS_LOGP>
7.26

> <JCHEM_LOGP>
8.23298693

> <ALOGPS_LOGS>
-7.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
96.93100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.21e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexabromobiphenyl

> <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 Br   UNK     0       1.334  -0.770   0.000  0.00  0.00          Br+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 Br   UNK     0       4.001  -5.390   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0      -1.334  -2.310   0.000  0.00  0.00          Br+0
HETATM   10  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       4.001 -10.010   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       1.334 -11.550   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2'4,4',5,5'-Hexabromo-1,1'-biphenyl	ChEBI
2,4,5,2',4',5'-Hexabromobiphenyl	ChEBI
PBB 153	ChEBI
PBB-153	ChEBI
PBB153	ChEBI
345-HBB	MeSH
245-HBB	MeSH

Chemical Formula

C₁₂H₄Br₆

Average Molecular Weight

627.584

Monoisotopic Molecular Weight

621.54132601

IUPAC Name

1,2,4-tribromo-5-(2,4,5-tribromophenyl)benzene

Traditional Name

hexabromobiphenyl

CAS Registry Number

Not Available

SMILES

BrC1=CC(Br)=C(C=C1Br)C1=CC(Br)=C(Br)C=C1Br

InChI Identifier

InChI=1S/C12H4Br6/c13-7-3-11(17)9(15)1-5(7)6-2-10(16)12(18)4-8(6)14/h1-4H

InChI Key

HMBBJSKXDBUNNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Polybrominated biphenyls

Alternative Parents

Substituents

Polybrominated biphenyl
Halobenzene
Bromobenzene
Aryl halide
Aryl bromide
Hydrocarbon derivative
Organobromide
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	7.26	ALOGPS
logP	8.23	ChemAxon
logS	-7.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.93 m³·mol⁻¹	ChemAxon
Polarizability	38.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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)	splash10-0aor-0169412000-5bb37ee3f8884a70e021	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’,4,4’,5,5’-Hexabromobiphenyl 10V, Positive-QTOF	splash10-00di-0000009000-e0aa9eb050e72925c23a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2’,4,4’,5,5’-Hexabromobiphenyl 20V, Positive-QTOF	splash10-00di-0000009000-0f29995fd0243bfb516e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2’,4,4’,5,5’-Hexabromobiphenyl 40V, Positive-QTOF	splash10-00di-0000009000-e006ad2b2c7966c23a60	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2’,4,4’,5,5’-Hexabromobiphenyl 10V, Negative-QTOF	splash10-00di-0000009000-bc06f4c474192eb9d7bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2’,4,4’,5,5’-Hexabromobiphenyl 20V, Negative-QTOF	splash10-00di-0000009000-bc06f4c474192eb9d7bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2’,4,4’,5,5’-Hexabromobiphenyl 40V, Negative-QTOF	splash10-00di-0000019000-444e52a299bf56d8faca	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

42948

PDB ID

Not Available

ChEBI ID

134050

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’,4,4’,5,5’-Hexabromobiphenyl (HMDB0341495)

MOL for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

3D MOL for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

3D SDF for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

3D-SDF for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

PDB for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

3D PDB for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

SMILES for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

INCHI for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

Structure for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

3D Structure for HMDB0341495 (2,2’,4,4’,5,5’-Hexabromobiphenyl)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra