1,2,7-Trichlorodibenzofuran
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Basic Info
| Common Name | 1,2,7-Trichlorodibenzofuran(F04658) |
| 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 | F04658 |
| CAS Number | 83704-37-4 |
| PubChem CID | 55117 |
| Formula | C12H5Cl3O |
| IUPAC Name | 1,2,7-trichlorodibenzofuran |
| InChI Key | AFOVQGPNOZDUEP-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H5Cl3O/c13-6-1-2-7-10(5-6)16-9-4-3-8(14)12(15)11(7)9/h1-5H |
| Canonical SMILES | C1=CC2=C(C=C1Cl)OC3=C2C(=C(C=C3)Cl)Cl |
| Isomeric SMILES | C1=CC2=C(C=C1Cl)OC3=C2C(=C(C=C3)Cl)Cl |
| Synonyms |
Dibenzofuran, 1,2,7-trichloro-
1,2,7-TRICHLORODIBENZOFURAN
UNII-AWD450P8B0
AWD450P8B0
Dibenzofuran, 1,2,7-trichloro
83704-37-4
AC1L1IEI
DTXSID90232550
AFOVQGPNOZDUEP-UHFFFAOYSA-N
UNII-698261N0VE component AFOVQGPNOZDUEP-UHFFFAOYSA-N
|
| 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 | Chlorinated dibenzofurans |
| Direct Parent | Polychlorinated dibenzofurans |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Polychlorinated dibenzofuran - Benzenoid - Aryl halide - Aryl chloride - Heteroaromatic compound - Furan - Oxacycle - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as polychlorinated dibenzofurans. These are organic compounds containing two or more chlorine atoms attached to a dibenzofuran moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 271.521 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 273 |
| Monoisotopic Mass | 269.941 |
| Exact Mass | 269.941 |
| XLogP | 5.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.9939 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.7194 |
| P-glycoprotein Substrate | Non-substrate | 0.7438 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7751 |
| Non-inhibitor | 0.6770 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7563 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4850 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7835 |
| CYP450 2D6 Substrate | Non-substrate | 0.8670 |
| CYP450 3A4 Substrate | Non-substrate | 0.6689 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9510 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5966 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8330 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8819 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7010 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8940 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7823 |
| Non-inhibitor | 0.8121 | |
| AMES Toxicity | Non AMES toxic | 0.5405 |
| Carcinogens | Non-carcinogens | 0.8040 |
| Fish Toxicity | High FHMT | 0.9368 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9987 |
| Honey Bee Toxicity | High HBT | 0.7402 |
| Biodegradation | Not ready biodegradable | 0.9754 |
| Acute Oral Toxicity | I | 0.7922 |
| Carcinogenicity (Three-class) | Danger | 0.5571 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.6993 | LogS |
| Caco-2 Permeability | 1.7144 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.3028 | LD50, mol/kg |
| Fish Toxicity | -0.5496 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.8293 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Stimulation or inhibition: Leaf microbial decomposition in streams subjected to complex chemical contamination. | Sci Total Environ | 2019 Jan 15 | 30340282 |
| Patulin removal from apple juice using a novel cysteine-functionalized metal-organic framework adsorbent. | Food Chem | 2019 Jan 1 | 30174021 |
| Lead and cadmium contamination in a large sample of United States infant formulas and baby foods. | Sci Total Environ | 2019 Feb 15 | 30253364 |
| Residual pollution and vegetation distribution in amended soils 20 years after a pyrite mine tailings spill (Aznalcóllar, Spain). | Sci Total Environ | 2019 Feb 10 | 30308867 |
| Liver histopathological alteration after repeated intra-tracheal instillation of titanium dioxide in male rats. | Gastroenterol Hepatol Bed Bench | 2018 Spring | 29910858 |
| 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 |
| Rationale and design of the Caloric Restriction and Exercise protection from Anthracycline Toxic Effects (CREATE) study: a 3-arm parallel group phase II randomized controlled trial in early breast cancer. | BMC Cancer | 2018 Sep 3 | 30176834 |
| Oleic Acid Alleviates Cadmium-Induced Oxidative Damage in Rat by Its Radicals Scavenging Activity. | Biol Trace Elem Res | 2018 Sep 29 | 30267311 |
| Application of bacteriophages in simultaneously controlling Escherichia coli O157:H7 and extended-spectrum beta-lactamase producing Escherichia coli. | Appl Microbiol Biotechnol | 2018 Sep 29 | 30267128 |
| In vitro antiplasmodial, antitrypanosomal and antileishmanial activities of selected medicinal plants from Ugandan flora: Refocusing into multi-component potentials. | J Ethnopharmacol | 2018 Sep 28 | 30273736 |
| <i>Dinophysis acuta</i> in Scottish Coastal Waters and Its Influence on Diarrhetic Shellfish Toxin Profiles. | Toxins (Basel) | 2018 Sep 28 | 30274219 |
| A NEW PAPER SENSOR METHOD FOR FIELD ANALYSIS OF ACID VOLATILE SULFIDES (AVS) IN SOILS. | Environ Toxicol Chem | 2018 Sep 26 | 30259571 |
| Evolution, and functional analysis of Natural Resistance-Associated Macrophage Proteins (NRAMPs) from Theobroma cacao and their role in cadmium accumulation. | Sci Rep | 2018 Sep 26 | 30258092 |
| Individual and combined toxicity of T-2 toxin and deoxynivalenol on human C-28/I2 and rat primary chondrocytes. | J Appl Toxicol | 2018 Sep 25 | 30251759 |
| Adducts formed during protein digestion decreased the toxicity of five carbonyl compounds against Caco-2 cells. | J Hazard Mater | 2018 Sep 24 | 30300775 |
| Evaluation of chemical extractants to assess metals phytoavailability in Brazilian municipal solid waste composts. | Environ Pollut | 2018 Sep 21 | 30267920 |
| Structural and Functional Analysis of the Gut Microbiome for Toxicologists. | Curr Protoc Toxicol | 2018 Sep 19 | 30230220 |
| Effect of chlorine on cultivability of Shiga toxin producing Escherichia coli (STEC) and β-lactamase genes carrying E. coli and Pseudomonas aeruginosa. | Int J Med Microbiol | 2018 Sep 18 | 30262431 |
| Carcinogenic and Non-carcinogenic Risk Assessment of Heavy Metals in Groundwater Wells in Neyshabur Plain, Iran. | Biol Trace Elem Res | 2018 Sep 17 | 30225757 |
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 ]