Pentabromodiphenyl ethers (T3D2040)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (7)XML
Targets (7)
Record Information
Version2.0
Creation Date2009-06-24 17:25:21 UTC
Update Date2014-12-24 20:25:06 UTC
Accession NumberT3D2040
Identification
Common NamePentabromodiphenyl ethers
ClassSmall Molecule
Description1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene is classified as a Food Contaminant (code WG) in the DFC.
Compound Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Ether
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Organobromide
  • Polybrominated Biphenyl
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene
2,2',4,4',5-PentaBDE
2,2',4,4',5-Pentabromodiphenyl ether
2,2',4,4',5-Pentabromodiphenyl ether solution
BDE 99
BDE No 99 solution
Benzene, 1,1'-oxybis-, pentabromo deriv
Benzene, 1,1'-oxybis-, pentabromo deriv.
Bromkal G 1
Diphenyl ether, pentabromo derivative
PBDE 99
Pentabromodiphenyl ether
Pentabromodiphenyl oxide
Pentabromodiphenyl oxide (technical)
Pentabromodiphenyl oxide (technical) (DE 71)
Pentabromodiphenyl oxide repackaged
Pentabromophenoxybenzene
Planelon PB 501
Saytex 125
Chemical FormulaC12H5Br5O
Average Molecular Mass564.688 g/mol
Monoisotopic Mass559.626 g/mol
CAS Registry Number32534-81-9
IUPAC Name1,2,4-tribromo-5-(2,4-dibromophenoxy)benzene
Traditional Namepentabromodiphenyl ether
SMILESBrC1=CC(Br)=C(OC2=C(Br)C=C(Br)C(Br)=C2)C=C1
InChI IdentifierInChI=1S/C12H5Br5O/c13-6-1-2-11(9(16)3-6)18-12-5-8(15)7(14)4-10(12)17/h1-5H
InChI KeyInChIKey=WHPVYXDFIXRKLN-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentBromodiphenyl 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceWhite crystalline solid.
Experimental Properties
PropertyValue
Melting Point-5°C
Boiling PointNot Available
Solubility9e-10 mg/mL at 20°C
LogP6.84
Predicted Properties
PropertyValueSource
Water Solubility0.0001 g/LALOGPS
logP6.69ALOGPS
logP7.32ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.41 m³·mol⁻¹ChemAxon
Polarizability35.27 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-0333940000-42dd8a3ed64cf167100b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000090000-809056b74a1ce70d7d442016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000090000-7f10ee2524d5c970e3732016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0100190000-14eb8c2cc4adb8070e882016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-d8c93920a7764fd1ef922016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000090000-ebc328172790629347c22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-0129870000-a7109e0d4d1b31b6f9382016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-fe5c3ca47b88f93a58cf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000090000-fe5c3ca47b88f93a58cf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v00-5029000000-50aada19d00650a28d0d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000090000-a36382b147d8b58ad72d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000090000-a36382b147d8b58ad72d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0nmi-0009850000-e3839609dbbe3d0ab1aa2021-09-22View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityLike other halogenated aromatic hydrocarbons, polybrominated diphenyl ethers bind to the cellular aryl hydrocarbon receptor (AhR), which regulates the synthesis of a variety of proteins. Activation of the AhR induces a number of enzymes, including cytochrome P-450-dependent monooxygenases of the CYP1A and CYP2B families, UDP-glucuronosyltransferase, and ethoxyresorufin-o-deethylase. PBDEs are also believed to disrupt the production, transport, and disposition of thyroid hormones. One mechanism of this involves metabolites ot PDBEs competing with thyroxine to bind to transthyretin, decreasing serum thyroid hormone levels. This change in thyroid hormone levels has been linked to both thyroid toxicity and neurobehavioral alterations. Certain PDBEs and their metabolites are also endocrine disruptors and may act as agonists at the estrogen receptors or antagonists at the androgen and progesterone receptors. (4, 1)
MetabolismPolybrominated biphenyls can be absorbed through oral, inhalation, and dermal routes. Once in the body they distribute throughout and bioaccumulate in the blood, breast milk, and adipose tissue. The extent of PBDE metabolism depends on the degree of bromination. Metabolism is believed to involve debromination and methylation, resulting in phenolic metabolites. Metabolized and unmetabolized PDBE compounds are excreted mainly in the faeces. (4, 6)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPolybrominated diphenyl ethers (PBDEs) are flame-retardant man-made chemicals found in plastics used in a variety of consumer products to make them difficult to burn. Pentabromodiphenyl ethers are most commonly used as a flame retardant in flexible polyurethane foam. (4, 5)
Minimum Risk LevelIntermediate Inhalation: 0.006 mg/m3 (3) Acute Oral: 0.03 mg/kg/day (3) Intermediate Oral: 0.007 mg/kg/day (3)
Health EffectsPolybrominated diphenyl ethers may affect the thyroid gland and liver. Animals studies have also shown that PDBEs can cause neurobehavioral alterations and affect the immune system. (4)
SymptomsNot Available
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB37516
PubChem Compound ID36159
ChEMBL IDNot Available
ChemSpider ID33255
KEGG IDC18203
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC086401
Stitch ID2,2',4,4',5-Pentabromobiphenyl Ether
PDB IDNot Available
ACToR ID4495
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Hamers T, Kamstra JH, Sonneveld E, Murk AJ, Kester MH, Andersson PL, Legler J, Brouwer A: In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol Sci. 2006 Jul;92(1):157-73. Epub 2006 Apr 6. [16601080 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. ATSDR - Agency for Toxic Substances and Disease Registry (2004). Toxicological profile for polybrominated biphenyls and polybrominated diphenyl ethers (PBBs and PBDEs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. Wikipedia. Octabromodiphenyl ether. Last Updated 13 May 2009. [Link]
  6. Wikipedia. Polybrominated diphenyl ether. Last Updated 19 June 2009. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

Target Details
1. Transthyretin
General Function:
Identical protein binding
Specific Function:
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name:
TTR
Uniprot ID:
P02766
Molecular Weight:
15886.88 Da
References
  1. Cao J, Lin Y, Guo LH, Zhang AQ, Wei Y, Yang Y: Structure-based investigation on the binding interaction of hydroxylated polybrominated diphenyl ethers with thyroxine transport proteins. Toxicology. 2010 Nov 9;277(1-3):20-8. doi: 10.1016/j.tox.2010.08.012. Epub 2010 Sep 8. [20804816 ]
  2. ATSDR - Agency for Toxic Substances and Disease Registry (2004). Toxicological profile for polybrominated biphenyls and polybrominated diphenyl ethers (PBBs and PBDEs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Target Details
2. Androgen receptor
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Hamers T, Kamstra JH, Sonneveld E, Murk AJ, Kester MH, Andersson PL, Legler J, Brouwer A: In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol Sci. 2006 Jul;92(1):157-73. Epub 2006 Apr 6. [16601080 ]
Target Details
3. Aryl hydrocarbon receptor
General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2004). Toxicological profile for polybrominated biphenyls and polybrominated diphenyl ethers (PBBs and PBDEs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Target Details
4. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2004). Toxicological profile for polybrominated biphenyls and polybrominated diphenyl ethers (PBBs and PBDEs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Target Details
5. Estrogen receptor beta
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (2004). Toxicological profile for polybrominated biphenyls and polybrominated diphenyl ethers (PBBs and PBDEs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Target Details
6. Progesterone receptor
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
References
  1. Hamers T, Kamstra JH, Sonneveld E, Murk AJ, Kester MH, Andersson PL, Legler J, Brouwer A: In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol Sci. 2006 Jul;92(1):157-73. Epub 2006 Apr 6. [16601080 ]
Target Details
7. Thyroxine-binding globulin
General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Major thyroid hormone transport protein in serum.
Gene Name:
SERPINA7
Uniprot ID:
P05543
Molecular Weight:
46324.12 Da
References
  1. Cao J, Lin Y, Guo LH, Zhang AQ, Wei Y, Yang Y: Structure-based investigation on the binding interaction of hydroxylated polybrominated diphenyl ethers with thyroxine transport proteins. Toxicology. 2010 Nov 9;277(1-3):20-8. doi: 10.1016/j.tox.2010.08.012. Epub 2010 Sep 8. [20804816 ]