4-Bromobiphenyl Ether
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Basic Info
| Common Name | 4-Bromobiphenyl Ether(F04444) |
| 2D Structure | |
| Description | Monobromodiphenyl ethers are organobromine compounds, as well as polybrominated diphenyl ethers containing one bromine atom. Polybrominated 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. PBDEs exist as mixtures of similar chemicals called congeners. Because they are mixed into plastics and foams rather than bound to them, PBDEs can leave the products that contain them and enter the environment. (L628) |
| FRCD ID | F04444 |
| CAS Number | 101-55-3 |
| PubChem CID | 7565 |
| Formula | C12H9BrO |
| IUPAC Name | 1-bromo-4-phenoxybenzene |
| InChI Key | JDUYPUMQALQRCN-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H9BrO/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9H |
| Canonical SMILES | C1=CC=C(C=C1)OC2=CC=C(C=C2)Br |
| Isomeric SMILES | C1=CC=C(C=C1)OC2=CC=C(C=C2)Br |
| Synonyms |
1-Bromo-4-phenoxybenzene
101-55-3
4-Bromodiphenyl ether
4-Bromophenyl phenyl ether
4-Bromophenoxybenzene
p-Bromodiphenyl ether
p-Phenoxybromobenzene
Benzene, 1-bromo-4-phenoxy-
P-BROMOPHENYL PHENYL ETHER
4-Bromodiphenylether
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Diphenylethers |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Bromodiphenyl ethers |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as bromodiphenyl ethers. These 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 249.107 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 2 |
| Complexity | 158 |
| Monoisotopic Mass | 247.984 |
| Exact Mass | 247.984 |
| XLogP | 4.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9803 |
| Human Intestinal Absorption | HIA+ | 0.9969 |
| Caco-2 Permeability | Caco2+ | 0.8402 |
| P-glycoprotein Substrate | Non-substrate | 0.7635 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8290 |
| Non-inhibitor | 0.9126 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7729 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7217 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8285 |
| CYP450 2D6 Substrate | Non-substrate | 0.8733 |
| CYP450 3A4 Substrate | Non-substrate | 0.6561 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9378 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5360 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9244 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.9349 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8955 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7463 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8459 |
| Non-inhibitor | 0.8648 | |
| AMES Toxicity | Non AMES toxic | 0.8928 |
| Carcinogens | Non-carcinogens | 0.7583 |
| Fish Toxicity | High FHMT | 0.9758 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9997 |
| Honey Bee Toxicity | High HBT | 0.8638 |
| Biodegradation | Not ready biodegradable | 0.9349 |
| Acute Oral Toxicity | III | 0.8643 |
| Carcinogenicity (Three-class) | Warning | 0.4687 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.6976 | LogS |
| Caco-2 Permeability | 1.6214 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8600 | LD50, mol/kg |
| Fish Toxicity | 0.0609 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 2.3543 | pIGC50, ug/L |
Targets
- 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
- Mechanism of Action:
- Certain PDBEs and their metabolites are also endocrine disruptors and may act as agonists at the estrogen receptors.
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp68.html
- 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
- Mechanism of Action:
- Certain PDBEs and their metabolites are also endocrine disruptors and may act as agonists at the estrogen receptors.
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp68.html
- 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
- Mechanism of Action:
- Certain PDBEs and their metabolites are also endocrine disruptors and may also act as agonists at the estrogen receptors or antagonists at the progesterone receptors.
References
- 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 ]
- 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
- Mechanism of Action:
- 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.
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp68.html
- 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
- Mechanism of Action:
- Certain PDBEs and their metabolites are also endocrine disruptors and may act as antagonists at the androgen receptors. ( A262)
References
- 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 ]
- 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
- Mechanism of Action:
- Like other halogenated aromatic hydrocarbons, PBDEs 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.
References
- 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). : http://www.atsdr.cdc.gov/toxprofiles/tp68.html