2,3,4,7,9-Pentachlorodibenzofuran
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Basic Info
| Common Name | 2,3,4,7,9-Pentachlorodibenzofuran(F04586) |
| 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 | F04586 |
| CAS Number | 70648-21-4 |
| PubChem CID | 51126 |
| Formula | C12H3Cl5O |
| IUPAC Name | 1,3,6,7,8-pentachlorodibenzofuran |
| InChI Key | FRLMQDUYUJIHCZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H3Cl5O/c13-4-1-6(14)9-5-3-7(15)10(16)11(17)12(5)18-8(9)2-4/h1-3H |
| Canonical SMILES | C1=C(C=C2C(=C1Cl)C3=CC(=C(C(=C3O2)Cl)Cl)Cl)Cl |
| Isomeric SMILES | C1=C(C=C2C(=C1Cl)C3=CC(=C(C(=C3O2)Cl)Cl)Cl)Cl |
| Synonyms |
1,3,6,7,8-PENTACHLORODIBENZOFURAN
UNII-479RK92V34
Dibenzofuran, 2,3,4,7,9-pentachloro
Dibenzofuran, 1,3,6,7,8-pentachloro-
CHEMBL334374
70648-21-4
479RK92V34
AC1L1AHJ
SCHEMBL2281295
CTK2I0094
|
| 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 | 340.405 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 328 |
| Monoisotopic Mass | 337.863 |
| Exact Mass | 339.86 |
| XLogP | 7 |
| Formal Charge | 0 |
| Heavy Atom Count | 18 |
| 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 |
Targets
- 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 ]
- 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 ]