1,2,3,7,8,9-Hexabromodibenzofuran
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Basic Info
| Common Name | 1,2,3,7,8,9-Hexabromodibenzofuran(F04547) |
| 2D Structure | |
| Description | Chlorinated dibenzofurans (CDFs) are a family of chemical that contain one to eight chlorine atoms attached to the carbon atoms of the parent chemical, dibenzofuran. The CDF family contains 135 individual compounds (known as congeners) with varying harmful health and environmental effects. Of these 135 compounds, those that contain chlorine atoms at the 2,3,7,8-positions of the parent dibenzofuran molecule are especially harmful. Other than for laboratory use of small amounts of CDFs for research and development purposes, these chemicals are not deliberately produced by industry. Most CDFs are produced in very small amounts as unwanted impurities of certain products and processes utilizing chlorinated compounds. Only a few of the 135 CDF compounds have been produced in large enough quantities so that their properties, such as color, smell, taste, and toxicity could be studied. (L952) |
| FRCD ID | F04547 |
| CAS Number | 161880-49-5 |
| PubChem CID | 44151788 |
| Formula | C12H2Br6O |
| IUPAC Name | 1,2,3,7,8,9-hexabromodibenzofuran |
| InChI Key | BWGBHHLGDVHQEM-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H2Br6O/c13-3-1-5-7(11(17)9(3)15)8-6(19-5)2-4(14)10(16)12(8)18/h1-2H |
| Canonical SMILES | C1=C2C(=C(C(=C1Br)Br)Br)C3=C(C(=C(C=C3O2)Br)Br)Br |
| Isomeric SMILES | C1=C2C(=C(C(=C1Br)Br)Br)C3=C(C(=C(C=C3O2)Br)Br)Br |
| Synonyms |
161880-49-5
1,2,3,7,8,9-Hexabromodibenzofuran
Dibenzofuran, 1,2,3,7,8,9-hexabromo-
1,2,3,7,8,9-HxBDF
CTK4D0995
AKOS030594133
Dibenzofuran,1,2,3,7,8,9-hexabromo-
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzofurans |
| Subclass | Dibenzofurans |
| Intermediate Tree Nodes | Brominated dibenzofurans |
| Direct Parent | Polybrominated dibenzofurans |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Polybrominated dibenzofuran - Polybrominated biphenyl - Benzenoid - Aryl halide - Aryl bromide - Heteroaromatic compound - Furan - Oxacycle - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organobromide - Organohalogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as polybrominated dibenzofurans. These are organic compounds containing two or more bromine atoms attached to a dibenzofuran moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 641.571 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 323 |
| Monoisotopic Mass | 635.521 |
| Exact Mass | 641.514 |
| XLogP | 7.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| 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+ | 0.9934 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6917 |
| P-glycoprotein Substrate | Non-substrate | 0.7334 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6713 |
| Non-inhibitor | 0.5490 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7524 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5817 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8176 |
| CYP450 2D6 Substrate | Non-substrate | 0.8580 |
| CYP450 3A4 Substrate | Non-substrate | 0.7056 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9315 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.7301 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8376 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8718 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.6971 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.9009 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8469 |
| Non-inhibitor | 0.7936 | |
| AMES Toxicity | Non AMES toxic | 0.6432 |
| Carcinogens | Non-carcinogens | 0.8461 |
| Fish Toxicity | High FHMT | 0.9305 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9996 |
| Honey Bee Toxicity | High HBT | 0.7373 |
| Biodegradation | Not ready biodegradable | 0.9759 |
| Acute Oral Toxicity | I | 0.5650 |
| Carcinogenicity (Three-class) | Danger | 0.5496 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.1889 | LogS |
| Caco-2 Permeability | 1.6887 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.9736 | LD50, mol/kg |
| Fish Toxicity | -0.4013 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.5942 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Citrus peel polymethoxyflavones, sudachitin and nobiletin, induce distinct cellular responses in human keratinocyte HaCaT cells. | Biosci Biotechnol Biochem | 2018 Sep 5 | 30185129 |
| Synephrine Hydrochloride Suppresses Esophageal Cancer Tumor Growth and Metastatic Potential through Inhibition of Galectin-3-AKT/ERK Signaling. | J Agric Food Chem | 2018 Sep 5 | 30113849 |
| Effect of a one-off sporidesmin challenge on the milk production of dairy cows. | N Z Vet J | 2018 Sep | 29949719 |
| Fumonisin B<sub>1</sub> exposure increases Hsp70 expression in the lung and kidney of rats without inducing significant oxidative stress. | Acta Vet Hung | 2018 Sep | 30264617 |
| Mechanism and Implication of the Sorption of Perfluorooctanoic Acid by Varying Soil Size Fractions. | J Agric Food Chem | 2018 Oct 26 | 30240199 |
| Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i>. | Mar Drugs | 2018 Oct 23 | 30360544 |
| Prevalence, Enterotoxin Genes, and Antibiotic Resistance of Bacillus cereus Isolated from Raw Vegetables in Korea. | J Food Prot | 2018 Oct | 30169119 |
| Selenium and drinking water quality indicators in Mongolia. | Environ Sci Pollut Res Int | 2018 Oct | 30094669 |
| Presence of Multidrug-Resistant Shiga Toxin-Producing Escherichia coli, Enteropathogenic Escherichia coli, and Enterotoxigenic Escherichia coli on Fresh Cheeses from Local Retail Markets in Mexico. | J Food Prot | 2018 Nov | 30272999 |
| Prevalence and characteristics of gastrointestinal infections in men who have sex with men diagnosed with rectal chlamydia infection in the UK: an 'unlinked anonymous' cross-sectional study. | Sex Transm Infect | 2018 Nov | 28360379 |
| Liquid chromatography - high resolution mass spectrometry method for monitoring of 17 mycotoxins in human plasma for exposure studies. | J Chromatogr A | 2018 May 4 | 29576275 |
| Development and validation of LC-MS/MS method for the determination of Ochratoxin A and its metabolite Ochratoxin α in poultry tissues and eggs. | J Environ Sci Health B | 2018 May 4 | 29393822 |
| Does Low-Protein Diet Influence the Uremic Toxin Serum Levels From the Gut Microbiota in Nondialysis Chronic Kidney Disease Patients? | J Ren Nutr | 2018 May | 29439931 |
| Forms of selenium in vitamin-mineral mixes differentially affect serum prolactin concentration and hepatic glutamine synthetase activity of steers grazing endophyte-infected tall fescue. | J Anim Sci | 2018 Mar 6 | 29385471 |
| Anesthetic activity of plant essential oils on Cyprinus carpio (koi carp). | Drug Discov Ther | 2018 Mar 19 | 29479046 |
| SERS strategy based on the modified Au nanoparticles for highly sensitive detection of bisphenol A residues in milk. | Talanta | 2018 Mar 1 | 29310247 |
| Antibiotic Resistance Profiling, Analysis of Virulence Aspects and Molecular Genotyping of Staphylococcus aureus Isolated in Sicily, Italy. | Foodborne Pathog Dis | 2018 Mar | 29260903 |
| Estimating population heat exposure and impacts on working people in conjunction with climate change. | Int J Biometeorol | 2018 Mar | 28766042 |
| Production of lutein, and polyunsaturated fatty acids by the acidophilic eukaryotic microalga Coccomyxa onubensis under abiotic stress by salt or ultraviolet light. | J Biosci Bioeng | 2018 Jun | 29370982 |
| Pyrrolizidine Alkaloids in Honey: Determination with Liquid Chromatography-mass Spectrometry Method. | J Vet Res | 2018 Jun | 30364911 |
Targets
- 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:
- Dibenzofurans bind the aryl hydrocarbon receptor, which increases its ability to activate transcription in the XRE promoter region. This alters the expression of a number of genes.
References
- Ni J, Pang ST, Yeh S: Differential retention of alpha-vitamin E is correlated with its transporter gene expression and growth inhibition efficacy in prostate cancer cells. Prostate. 2007 Apr 1;67(5):463-71. [17252538 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]