PBDE 153 (CED0013186)

Record Information

Version

1.0

Creation Date

2016-05-19 02:33:32 UTC

Update Date

2026-08-18 21:11:11 UTC

SynCED ID

CED0013186

Secondary Accession Numbers

CHEM007950

Identification

Common Name

PBDE 153

Class

Small Molecule

Description

PBDE 153 (C12H4Br6O) is a chemical compound. PBDE 153 belongs to the diphenylethers, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 643.58 g/mol, PBDE 153 is a heavy molecule. This compound is found in or released from one recorded source: indoor air via air, dust, and atmospheric transport. The recorded exposure route for PBDE 153 is inhalation. Various health effects have been associated with this compound. It is associated with breast cancer (PMC12505496 ) and gestational diabetes (PMC10807361 ). Additionally, PBDE 153 is associated with an increase in hyperactivity (PMC10807361 ). Conversely, it is associated with inverse relationships regarding obesity (PMC8632231 ), overweight (PMC8632231 ), and autism spectrum disorder (PMC10807361 ).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
BDE 153	Kegg
1,1'-Oxybis(2,4,5-tribromo-benzene	HMDB
1,1'-Oxybis(2,4,5-tribromobenzene)	HMDB
1,1'-Oxybis[2,4,5-tribromo]benzene, 9ci	HMDB
PBDE 153	HMDB
2,2',4,4',5,5'-Brominated diphenyl ether	MeSH, HMDB
BDE-153	MeSH, HMDB
Hexabrominated diphenyl ether 153	MeSH, HMDB
2,2',4,4',5,5'-HexaBDE	MeSH
2,2',4,4',5,5'-Hexabrominated diphenyl ether	MeSH

Chemical Formula

C₁₂H₄Br₆O

Average Molecular Mass

643.584 g/mol

Monoisotopic Mass

637.536 g/mol

CAS Registry Number

68631-49-2

IUPAC Name

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

Traditional Name

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

SMILES

BrC1=CC(Br)=C(Br)C=C1OC1=CC(Br)=C(Br)C=C1Br

InChI Identifier

InChI=1S/C12H4Br6O/c13-5-1-9(17)11(3-7(5)15)19-12-4-8(16)6(14)2-10(12)18/h1-4H

InChI Key

RZXIRSKYBISPGF-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:81534 )
aromatic ether (CHEBI:81534 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

endocrine disruptor (PMC5328929 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.4e-05 g/L	ALOGPS
logP	6.96	ALOGPS
logP	8.09	ChemAxon
logS	-6.9	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	98.04 m³·mol⁻¹	ChemAxon
Polarizability	38.56 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0007-0303069000-275c51e6ae330a9c3349	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-544287a5e14202091215	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-4fbf1382e2577b5f8a1f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-cae4a9624bcee58b3a1f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-4025e2feaafd48f4ee05	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-97021805d371ebfeaf0b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0001019000-91c63791b2bbf507bfea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-36ea251732d85a115164	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-36ea251732d85a115164	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-5009001000-708a58d4383a82090683	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-e6acdfa82a26ae7e228b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0000009000-e6acdfa82a26ae7e228b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0019-0020469000-5279e58210c6d0d1b956	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
3155.0 Log mg/kg [1800:5600]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
hypertension	Associated With?	increase	A disorder characterized by a pathological increase in blood pressure; a repeatedly elevation in the blood pressure exceeding 140 over 90 mm Hg. (NCI CTCAE)	PMC11245865
hypertension	Associated With?	Not Available	A disorder characterized by a pathological increase in blood pressure; a repeatedly elevation in the blood pressure exceeding 140 over 90 mm Hg. (NCI CTCAE)	PMC11245865
breast cancer	Associated With?	Not Available	A breast cancer that has material basis in abnormally proliferating cells derives from epithelial cells. (DO)	PMC12505496
overweight	Associated With?	inverse	Not Available	PMC8632231
gestational diabetes	Associated With?	Not Available	A disorder, occurring in pregnant women, characterized by hyperglycemia.	PMC10807361
asthma	Associated With?	Not Available	A bronchial disease that is characterized by chronic inflammation and narrowing of the airways, which is caused by a combination of environmental and genetic factors. The disease has symptom recurring periods of wheezing (a whistling sound while breathing), has symptom chest tightness, has symptom shortness of breath, has symptom mucus production and has symptom coughing. The symptoms appear due to a variety of triggers such as allergens, irritants, respiratory infections, weather changes, exercise, stress, reflux disease, medications, foods and emotional anxiety. (DO)	PMC12553576 , PMC12553576
asthma	Associated With?	increase	A bronchial disease that is characterized by chronic inflammation and narrowing of the airways, which is caused by a combination of environmental and genetic factors. The disease has symptom recurring periods of wheezing (a whistling sound while breathing), has symptom chest tightness, has symptom shortness of breath, has symptom mucus production and has symptom coughing. The symptoms appear due to a variety of triggers such as allergens, irritants, respiratory infections, weather changes, exercise, stress, reflux disease, medications, foods and emotional anxiety. (DO)	PMC12553576
diabetes mellitus	Associated With?	positive	A glucose metabolism disease characterized by chronic hyperglycaemia with disturbances of carbohydrate, fat and protein metabolism resulting from defects in insulin secretion, insulin action, or both. (DO)	PMC10063979
diabetes mellitus	Associated With?	Not Available	A glucose metabolism disease characterized by chronic hyperglycaemia with disturbances of carbohydrate, fat and protein metabolism resulting from defects in insulin secretion, insulin action, or both. (DO)	PMC12755720 , PMC2518348
obesity	Associated With?	inverse	A disorder characterized by having a high amount of body fat. (NCI CTCAE)	PMC8632231
hyperactivity	Associated With?	increase	A condition characterized by increased movement, impulsive actions, and a shorter attention span, and being easily distracted.	PMC10807361 , PMC10807361
autism spectrum disorder	Associated With?	inverse	A pervasive developmental disorder that is a spectrum of psychological conditions. The disease has_symptom widespread abnormalities of social interactions and communication, has_symptom severely restricted interests and has symptom highly repetitive behavior.	PMC10807361
abdominal obesity-metabolic syndrome	Associated With?	Not Available	Not Available	PMC12755720 , PMC3983240
Adiposity	Associated With?	inverse	Not Available	PMC6400314
Waist Circumference	Associated With?	decrease	Not Available	PMC10807361
Waist Circumference	Associated With?	inverse	Not Available	PMC6400314 , PMC6400314
Premature birth	Associated With?	Not Available	Not Available	PMC10807361
Time-to-Pregnancy	Associated With?	increase	Not Available	PMC10100123
Fertility	Associated With?	decrease	Not Available	PMC10100123
Aggressive behavior	Associated With?	decrease	Not Available	PMC10807361 , PMC10807361
Aggressive behavior	Associated With?	increase	Not Available	PMC5567986
Executive Function	Associated With?	Not Available	Not Available	PMC4821747
Live Birth	Associated With?	increase	Not Available	PMC10100123
Activities of Daily Living	Associated With?	Not Available	Not Available	PMC10807361

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000019	Indoor air?Indoor air can be a significant reservoir for synthetic chemical contaminants, which often originate from various sources within enclosed environments.	Air, dust & atmospheric transport	Not Available
CEDs000476	Biosolids?Biosolids are nutrient-rich organic materials derived from the treatment of sewage sludge during wastewater management processes.	Wastewater, sanitation & biosolids	PMC4013270
CEDs000743	Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.	Wastewater, sanitation & biosolids	PubChem
CEDs01148	Milk	Food, food processing & cookware	PMC7009407 , PMC10807361
CEDs01152	Food Chain	Food, food processing & cookware	PMC2022639
CEDs01153	Breast Milk	Food, food processing & cookware	PMC6592971 , PMC6592971
CEDs01154	Human Milk	Food, food processing & cookware	PMC10807361 , PMC10702444
CEDs01170	Eggs	Food, food processing & cookware	PMC8252721 , PMC9500368
CEDs01294	Breast Milk Samples	Food, food processing & cookware	PMC3885979
CEDs01299	Food Categories	Food, food processing & cookware	PMC10807361
CEDs01488	Food Supply	Food, food processing & cookware	PMC2951838
CEDs01666	Beef Liver	Food, food processing & cookware	PMC8539179
CEDs02255	Water	Aquatic systems & sediments	PMC8252721 , PMC6068772
CEDs02264	Sediment	Aquatic systems & sediments	PMC6068772
CEDs02270	River	Aquatic systems & sediments	PMC6068772 , PMC6068772
CEDs02278	Sediment Surface	Aquatic systems & sediments	PMC6068772
CEDs02449	Marine Mammals	Aquatic systems & sediments	PMC3047442
CEDs02477	Aquatic Organisms	Aquatic systems & sediments	PMC9916311
CEDs02589	Air	Air, dust & atmospheric transport	PMC8252721
CEDs02933	Indoor Environment	Household items	PMC2951838
CEDs03017	Sludge	Wastewater, sanitation & biosolids	PMC6068772
CEDs03023	Effluent Samples	Wastewater, sanitation & biosolids	PMC6068772

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.323 Statistical Significance 0.0934 Supporting Reference Compounds 955 E-value 727.112
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P08909	Rat	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.323 Statistical Significance 0.0281 Supporting Reference Compounds 185 E-value 218.912
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.273 Applicability Domain 0.323 Statistical Significance 0.0736 Supporting Reference Compounds 380 E-value 573.126
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P30994	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.303 Statistical Significance 0.0817 Supporting Reference Compounds 40 E-value 636.184
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.204 Applicability Domain 0.303 Statistical Significance 0.6054 Supporting Reference Compounds 541 E-value 4713.23
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.204 Applicability Domain 0.323 Statistical Significance 0.7658 Supporting Reference Compounds 823 E-value 5961.85
Click to view 3D structure	Isocitrate lyase	Q9P8Q7	Candida albicans	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.2 Low confidence Statistical Significance 0.0022 Supporting Reference Compounds 1 E-value 17.1268
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.193 Applicability Domain 0.214 Low confidence Statistical Significance 0.6588 Supporting Reference Compounds 472 E-value 5128.78
Click to view 3D structure	Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2	Q6P549	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.192 Applicability Domain 0.192 Low confidence Statistical Significance 4.70e-04 Supporting Reference Compounds 1 E-value 3.65891
Click to view 3D structure	Type II inositol 1,4,5-trisphosphate 5-phosphatase	P32019	Humans	Predicted (SEA)	Prediction Confidence Score 0.192 Applicability Domain 0.192 Low confidence Statistical Significance 4.70e-04 Supporting Reference Compounds 1 E-value 3.65891
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	Prediction Confidence Score 0.19 Applicability Domain 0.214 Low confidence Statistical Significance 0.6334 Supporting Reference Compounds 372 E-value 4931.05
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	Prediction Confidence Score 0.181 Applicability Domain 0.3 Statistical Significance 0.9605 Supporting Reference Compounds 1130 E-value 7477.11
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.212 Low confidence Statistical Significance 0.7295 Supporting Reference Compounds 332 E-value 5678.94
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	Prediction Confidence Score 0.178 Applicability Domain 0.214 Low confidence Statistical Significance 0.7727 Supporting Reference Compounds 407 E-value 6015.33
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	Prediction Confidence Score 0.176 Applicability Domain 0.212 Low confidence Statistical Significance 0.5968 Supporting Reference Compounds 172 E-value 4646.27
Click to view 3D structure	Tyrosine-protein kinase Fyn	P06241	Humans	Predicted (SEA)	Prediction Confidence Score 0.176 Applicability Domain 0.3 Statistical Significance 0.9518 Supporting Reference Compounds 707 E-value 7409.61
Click to view 3D structure	Trace amine-associated receptor 1	Q96RJ0	Humans	Predicted (SEA)	Prediction Confidence Score 0.173 Applicability Domain 0.323 Statistical Significance 0.4734 Supporting Reference Compounds 63 E-value 3685.07
Click to view 3D structure	Enoyl-acyl-carrier protein reductase	Q965D5	Plasmodium falciparum	Predicted (SEA)	Prediction Confidence Score 0.173 Applicability Domain 0.219 Low confidence Statistical Significance 0.0283 Supporting Reference Compounds 18 E-value 220.625
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	Prediction Confidence Score 0.173 Applicability Domain 0.193 Low confidence Statistical Significance 0.9765 Supporting Reference Compounds 1301 E-value 7602.29
Click to view 3D structure	Insulin-like growth factor 1 receptor	P08069	Humans	Predicted (SEA)	Prediction Confidence Score 0.172 Applicability Domain 0.193 Low confidence Statistical Significance 0.957 Supporting Reference Compounds 785 E-value 7450.4
Click to view 3D structure	Polyunsaturated fatty acid lipoxygenase ALOX15	P16050	Humans	Predicted (SEA)	Prediction Confidence Score 0.172 Applicability Domain 0.281 Low confidence Statistical Significance 0.28 Supporting Reference Compounds 46 E-value 2179.47
Click to view 3D structure	Low molecular weight phosphotyrosine protein phosphatase	Q9D358	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.172 Applicability Domain 0.189 Low confidence Statistical Significance 0.0254 Supporting Reference Compounds 2 E-value 198.126
Click to view 3D structure	Low molecular weight phosphotyrosine protein phosphatase	P41498	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.172 Applicability Domain 0.189 Low confidence Statistical Significance 0.0254 Supporting Reference Compounds 2 E-value 198.126
Click to view 3D structure	Complement factor D	P32038	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.171 Applicability Domain 0.171 Low confidence Statistical Significance 0.0508 Supporting Reference Compounds 1 E-value 395.785
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	Prediction Confidence Score 0.167 Applicability Domain 0.193 Low confidence Statistical Significance 0.9749 Supporting Reference Compounds 1274 E-value 7589.83
Click to view 3D structure	Thyroxine-binding globulin	P05543	Humans	Known	Not Available