2-Bromodibenzofuran
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Basic Info
| Common Name | 2-Bromodibenzofuran(F04624) |
| 2D Structure | |
| Description | 2-Bromodibenzofuran is a halogenated dibenzofuran. It is relatively nontoxic although it is irritating to mucous membranes and the upper respiratory tract. It is primarily a laboratory chemical although it can be generated from the production of coal tar or coal gas. |
| FRCD ID | F04624 |
| CAS Number | 86-76-0 |
| PubChem CID | 6856 |
| Formula | C12H7BrO |
| IUPAC Name | 2-bromodibenzofuran |
| InChI Key | CRJISNQTZDMKQD-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H7BrO/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-7H |
| Canonical SMILES | C1=CC=C2C(=C1)C3=C(O2)C=CC(=C3)Br |
| Isomeric SMILES | C1=CC=C2C(=C1)C3=C(O2)C=CC(=C3)Br |
| Synonyms |
2-BROMODIBENZOFURAN
2-Bromodibenzo[b]furan
2-Bromodibenzo[b,d]furan
86-76-0
2-BROMO-DIBENZOFURAN
Dibenzofuran, 2-bromo-
Dibenzofuran, 2-bromo- (8CI)(9CI)
CRJISNQTZDMKQD-UHFFFAOYSA-N
NSC1735
NSC 1735
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzofurans |
| Subclass | Dibenzofurans |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dibenzofurans |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Dibenzofuran - 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 dibenzofurans. These are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 247.091 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 218 |
| Monoisotopic Mass | 245.968 |
| Exact Mass | 245.968 |
| XLogP | 4.8 |
| 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+ | 0.9920 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6643 |
| P-glycoprotein Substrate | Non-substrate | 0.7372 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7881 |
| Inhibitor | 0.5314 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7497 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6977 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8294 |
| CYP450 2D6 Substrate | Non-substrate | 0.8598 |
| CYP450 3A4 Substrate | Non-substrate | 0.7227 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8649 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6059 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8156 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8271 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7918 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7890 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8434 |
| Non-inhibitor | 0.8160 | |
| AMES Toxicity | AMES toxic | 0.6668 |
| Carcinogens | Non-carcinogens | 0.8265 |
| Fish Toxicity | High FHMT | 0.9043 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9998 |
| Honey Bee Toxicity | High HBT | 0.7873 |
| Biodegradation | Not ready biodegradable | 0.9720 |
| Acute Oral Toxicity | III | 0.4857 |
| Carcinogenicity (Three-class) | Danger | 0.4951 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.4198 | LogS |
| Caco-2 Permeability | 1.5882 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.2271 | LD50, mol/kg |
| Fish Toxicity | -0.1106 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.3483 | 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
- Toxicology and Carcinogenesis Studies of Bromoethane (Ethyl Bromide) (CAS No. 74-96-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1989 Oct;363:1-186. [12695778 ]
- 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 ]