1,3,4,6,8-Pentachlorodibenzofuran
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Basic Info
| Common Name | 1,3,4,6,8-Pentachlorodibenzofuran(F04579) |
| 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 | F04579 |
| CAS Number | 83704-55-6 |
| PubChem CID | 55135 |
| Formula | C12H3Cl5O |
| IUPAC Name | 1,3,4,6,8-pentachlorodibenzofuran |
| InChI Key | COKIAYPRHYHYCH-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H3Cl5O/c13-4-1-5-9-6(14)3-7(15)10(17)12(9)18-11(5)8(16)2-4/h1-3H |
| Canonical SMILES | C1=C(C=C2C3=C(C(=C(C=C3Cl)Cl)Cl)OC2=C1Cl)Cl |
| Isomeric SMILES | C1=C(C=C2C3=C(C(=C(C=C3Cl)Cl)Cl)OC2=C1Cl)Cl |
| Synonyms |
1,3,4,6,8-PENTACHLORODIBENZOFURAN
UNII-ME6P0421KM
Dibenzofuran, 1,3,4,6,8-pentachloro
ME6P0421KM
83704-55-6
Dibenzofuran, 1,3,4,6,8-pentachloro-
AC1L1IG0
CTK5F0991
DTXSID20232568
COKIAYPRHYHYCH-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 | 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 | 6.2 |
| 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Consensus toxicity factors for polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls combining in silico models and extensive in vitro screening of AhR-mediated effects in human and rodent cells. | Chem Res Toxicol | 2015 Apr 20 | 25654323 |
| Polychlorinated dibenzo-p-dioxins and dibenzofurans in water and six fish species from Dongting Lake, China. | Chemosphere | 2014 Nov | 25113196 |
| Relative potency based on hepatic enzyme induction predicts immunosuppressive effects of a mixture of PCDDS/PCDFS and PCBS. | Toxicol Appl Pharmacol | 2008 Mar 15 | 18190939 |
| Dioxin concentration in the blood of patients collected during medical check-up for Yusho in 2004-2005. | Fukuoka Igaku Zasshi | 2007 May | 17642301 |
| Toxicology and carcinogenesis studies of a mixture of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) (Cas No. 1746-01-6), 2,3,4,7,8-pentachlorodibenzofuran (PeCDF) (Cas No. 57117-31-4), and 3,3',4,4',5-pentachlorobiphenyl (PCB 126) (Cas No. 57465-28-8) in female Harlan Sprague-Dawley rats (gavage studies). | Natl Toxicol Program Tech Rep Ser | 2006 Sep | 17342195 |
| Toxicology and carcinogenesis studies of 2,3,4,7,8-pentachlorodibenzofuran (PeCDF) (Cas No. 57117-31-4) in female Harlan Sprague-Dawley rats (gavage studies). | Natl Toxicol Program Tech Rep Ser | 2006 Sep | 17160103 |
| Active elimination of causative PCDFs/DDs congeners of Yusho by one year intake of FBRA in Japanese people. | Fukuoka Igaku Zasshi | 2003 May | 12872712 |
| [Levels of PCDDs, PCDFs and coplanar PCBs in the blood and stool of Taiwanese Yu-Cheng patients]. | Fukuoka Igaku Zasshi | 1995 May | 7628814 |
| Elimination of polychlorinated dibenzofurans (PCDFs) and polychlorinated biphenyls (PCBs) from human blood in the Yusho and Yu-Cheng rice oil poisonings. | Arch Environ Contam Toxicol | 1993 May | 8507107 |
| [Therapeutic trial for promotion of fecal excretion of PCDFs and PCBs by the administration of cholestyramine in Yusho patients]. | Fukuoka Igaku Zasshi | 1991 May | 1916604 |
| [Polychlorinated dibenzofurans (PCDFs) in the subcutaneous adipose tissue of yusho patients and normal controls]. | Fukuoka Igaku Zasshi | 1989 May | 2501196 |
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 ]