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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 22:47:56 UTC

Update Date

2022-03-07 02:55:23 UTC

HMDB ID

HMDB0037547

Secondary Accession Numbers

HMDB37547

Metabolite Identification

Common Name

1,1'-Oxybis[2,4-dibromobenzene]

Description

1,1'-Oxybis[2,4-dibromobenzene], also known as PBDE 47, belongs to the class of organic compounds known as bromodiphenyl ethers. Bromodiphenyl ethers are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group. 1,1'-Oxybis[2,4-dibromobenzene] is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on 1,1'-Oxybis[2,4-dibromobenzene].

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241217562D          

 17 18  0  0  0  0            999 V2000
   -1.2376    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239    1.0712    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253    1.0712    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2991   -0.3566    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991   -0.3566    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037547

> <DATABASE_NAME>
hmdb

> <SMILES>
BrC1=CC=C(OC2=CC=C(Br)C=C2Br)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H6Br4O/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6H

> <INCHI_KEY>
XYBSIYMGXVUVGY-UHFFFAOYSA-N

> <FORMULA>
C12H6Br4O

> <MOLECULAR_WEIGHT>
485.791

> <EXACT_MASS>
481.715215402

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
32.03758066988883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4-dibromo-1-(2,4-dibromophenoxy)benzene

> <ALOGPS_LOGP>
6.37

> <JCHEM_LOGP>
6.5485435003333325

> <ALOGPS_LOGS>
-6.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.087832657574749

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
82.79000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dibromo-1-(2,4-dibromophenoxy)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  C   UNK     0      -2.310   0.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.849   0.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.619  -0.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.849  -2.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.310  -2.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.541  -0.666   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.001  -0.666   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.538  -0.666   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.307  -2.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.849  -2.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.619  -0.666   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.849   0.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.307   0.668   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       1.538   2.000   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0      -1.541   2.000   0.000  0.00  0.00          Br+0
HETATM   16 Br   UNK     0       6.158  -0.666   0.000  0.00  0.00          Br+0
HETATM   17 Br   UNK     0      -6.158  -0.666   0.000  0.00  0.00          Br+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13    8   12   14                                                  
CONECT   14   13                                                            
CONECT   15    1                                                            
CONECT   16   11                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PBDE 47	Kegg
BDE 47	Kegg
1,1'-Oxybis(2,4-dibromo-benzene	HMDB
1,1'-Oxybis(2,4-dibromobenzene)	HMDB
1,1'-Oxybis[2,4-dibromobenzene], 9ci	HMDB
2,2',4,4'-TetraBDE	HMDB
2,2',4,4'-Tetrabromodiphenyl ether	HMDB, MeSH
2,2'4,4'-Tetrabromodiphenyl ether	HMDB
Dibromophenyl ether	HMDB
PBDE-47	HMDB, MeSH
BDE-47	MeSH
2,2',4,4'-Tetrabromobiphenyl ether	MeSH
2,2,4,4-Tetrabromodiphenyl ether	MeSH
TBDP-Ether	MeSH
Tetrabrominated diphenyl ether 47	MeSH
2,2',4,4'-Brominated diphenyl ether	MeSH

Chemical Formula

C₁₂H₆Br₄O

Average Molecular Weight

485.791

Monoisotopic Molecular Weight

481.715215402

IUPAC Name

2,4-dibromo-1-(2,4-dibromophenoxy)benzene

Traditional Name

2,4-dibromo-1-(2,4-dibromophenoxy)benzene

CAS Registry Number

5436-43-1

SMILES

BrC1=CC=C(OC2=CC=C(Br)C=C2Br)C(Br)=C1

InChI Identifier

InChI=1S/C12H6Br4O/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6H

InChI Key

XYBSIYMGXVUVGY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bromodiphenyl ethers. Bromodiphenyl ethers are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Bromodiphenyl ethers

Alternative Parents

Substituents

Bromodiphenyl ether
Diaryl ether
Phenoxy compound
Phenol ether
Halobenzene
Bromobenzene
Aryl halide
Aryl bromide
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:81584 )
aromatic ether (CHEBI:81584 )
PBDEs (C18205 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037547)

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0037547)

Cellular substructure

Membrane (HMDB: HMDB0037547)

Source

Exogenous

Food

Food (HMDB: HMDB0037547)

Not Available

Nutrient (HMDB: HMDB0037547)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	82 - 82.5 °C	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
Water Solubility	0.00017 g/L	ALOGPS
logP	6.37	ALOGPS
logP	6.55	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.79 m³·mol⁻¹	ChemAxon
Polarizability	32.04 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]+	157.306	30932474
DeepCCS	[M-H]-	154.948	30932474
DeepCCS	[M-2H]-	187.849	30932474
DeepCCS	[M+Na]+	163.399	30932474
AllCCS	[M+H]+	178.8	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	181.1	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	133.7	32859911
AllCCS	[M+Na-2H]-	133.7	32859911
AllCCS	[M+HCOO]-	133.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,1'-Oxybis[2,4-dibromobenzene]	BrC1=CC=C(OC2=CC=C(Br)C=C2Br)C(Br)=C1	3454.0	Standard polar	33892256
1,1'-Oxybis[2,4-dibromobenzene]	BrC1=CC=C(OC2=CC=C(Br)C=C2Br)C(Br)=C1	2440.6	Standard non polar	33892256
1,1'-Oxybis[2,4-dibromobenzene]	BrC1=CC=C(OC2=CC=C(Br)C=C2Br)C(Br)=C1	2588.7	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 - 1,1'-Oxybis[2,4-dibromobenzene] GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1463900000-7da45be6416ebb6a1e7d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 10V, Positive-QTOF	splash10-001i-0000900000-d4c66d8d494e6dd333d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 20V, Positive-QTOF	splash10-001i-0000900000-d4c66d8d494e6dd333d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 40V, Positive-QTOF	splash10-001i-0101900000-911c5f9c655f019b2da7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 10V, Negative-QTOF	splash10-001i-0000900000-d877d4cecf0a17e261c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 20V, Negative-QTOF	splash10-001i-0000900000-c2779919089e7a3fc42a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 40V, Negative-QTOF	splash10-00aj-0287900000-0b3bbde2ea7e8314162f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 10V, Negative-QTOF	splash10-001i-0000900000-6a84f0829b1c8e950481	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 20V, Negative-QTOF	splash10-001i-0000900000-6a84f0829b1c8e950481	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 40V, Negative-QTOF	splash10-00fr-3090400000-a1f6b7b929a169d529b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 10V, Positive-QTOF	splash10-001i-0000900000-cf061a72daf38efad675	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 20V, Positive-QTOF	splash10-001i-0000900000-cf061a72daf38efad675	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1'-Oxybis[2,4-dibromobenzene] 40V, Positive-QTOF	splash10-00di-0093200000-94003a3b97f67ce64910	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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 and Quantified	0.00027(0.00023-0.00033) uM	Adult (>18 years old)	Both	Normal	Report on Human B...	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

FDB016629

KNApSAcK ID

Not Available

Chemspider ID

85876

KEGG Compound ID

C18205

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95170

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

Gascon M, Vrijheid M, Martinez D, Forns J, Grimalt JO, Torrent M, Sunyer J: Effects of pre and postnatal exposure to low levels of polybromodiphenyl ethers on neurodevelopment and thyroid hormone levels at 4 years of age. Environ Int. 2011 Apr;37(3):605-11. doi: 10.1016/j.envint.2010.12.005. Epub 2011 Jan 14. [PubMed:21237513 ]
Stocker J, Scheringer M, Wegmann F, Hungerbuhler K: Modeling the effect of snow and ice on the global environmental fate and long-range transport potential of semivolatile organic compounds. Environ Sci Technol. 2007 Sep 1;41(17):6192-8. [PubMed:17937301 ]
Sprague M, Dick JR, Medina A, Tocher DR, Bell JG, Mourente G: Lipid and fatty acid composition, and persistent organic pollutant levels in tissues of migrating Atlantic bluefin tuna (Thunnus thynnus, L.) broodstock. Environ Pollut. 2012 Dec;171:61-71. doi: 10.1016/j.envpol.2012.07.021. Epub 2012 Aug 9. [PubMed:22885218 ]
Bocquene G, Abarnou A: Organochlorinated pesticides, PCBs, dioxins, and PBDEs in grey mullets (Liza ramada) and allis shads (Alosa alosa) from the Vilaine estuary (France). Environ Sci Pollut Res Int. 2013 Feb;20(2):667-75. doi: 10.1007/s11356-012-1206-4. Epub 2012 Sep 27. [PubMed:23014954 ]
Zhao G, Wang Z, Zhou H, Zhao Q: Burdens of PBBs, PBDEs, and PCBs in tissues of the cancer patients in the e-waste disassembly sites in Zhejiang, China. Sci Total Environ. 2009 Aug 15;407(17):4831-7. doi: 10.1016/j.scitotenv.2009.05.031. Epub 2009 Jun 17. [PubMed:19539352 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1,1'-Oxybis[2,4-dibromobenzene] (HMDB0037547)

MOL for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

3D MOL for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

3D SDF for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

3D-SDF for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

PDB for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

3D PDB for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

SMILES for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

INCHI for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

Structure for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

3D Structure for HMDB0037547 (1,1'-Oxybis[2,4-dibromobenzene])

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra