1,2-Dibromoethane
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Basic Info
| Common Name | 1,2-Dibromoethane(F03295) |
| 2D Structure | |
| Description | 1,2-Dibromoethane, also known as ethylene dibromide (EDB), is the organobromine compound with the chemical formula (CH2Br)2. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a colorless liquid with a sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant. The effects on people of breathing high levels are not known, but animal studies with short-term exposures to high levels caused depression and collapse, indicating effects on the brain. |
| FRCD ID | F03295 |
| CAS Number | 106-93-4 |
| PubChem CID | 7839 |
| Formula | C2H4Br2 |
| IUPAC Name | 1,2-dibromoethane |
| InChI Key | PAAZPARNPHGIKF-UHFFFAOYSA-N |
| InChI | InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2 |
| Canonical SMILES | C(CBr)Br |
| Isomeric SMILES | C(CBr)Br |
| Synonyms |
1,2-Dibromoethane
106-93-4
ETHYLENE DIBROMIDE
Ethylene bromide
sym-Dibromoethane
Ethane, 1,2-dibromo-
alpha,beta-Dibromoethane
Bromuro di etile
1,2-Dibromaethan
1,2-Dibroomethaan
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organohalogen compounds |
| Class | Organobromides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Organobromides |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Hydrocarbon derivative - Organobromide - Alkyl halide - Alkyl bromide - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as organobromides. These are compounds containing a chemical bond between a carbon atom and a bromine atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 187.862 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 1 |
| Complexity | 6 |
| Monoisotopic Mass | 185.868 |
| Exact Mass | 187.866 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 4 |
| 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+ | 0.9680 |
| Human Intestinal Absorption | HIA+ | 0.9804 |
| Caco-2 Permeability | Caco2+ | 0.7544 |
| P-glycoprotein Substrate | Non-substrate | 0.8557 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9588 |
| Non-inhibitor | 0.8940 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7780 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5048 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8439 |
| CYP450 2D6 Substrate | Non-substrate | 0.7084 |
| CYP450 3A4 Substrate | Non-substrate | 0.7692 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7368 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8624 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9592 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8449 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9705 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8243 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8724 |
| Non-inhibitor | 0.9463 | |
| AMES Toxicity | AMES toxic | 0.9175 |
| Carcinogens | Carcinogens | 0.6813 |
| Fish Toxicity | Low FHMT | 0.6474 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9877 |
| Honey Bee Toxicity | High HBT | 0.8008 |
| Biodegradation | Not ready biodegradable | 0.8515 |
| Acute Oral Toxicity | II | 0.7429 |
| Carcinogenicity (Three-class) | Danger | 0.5843 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.7424 | LogS |
| Caco-2 Permeability | 1.6775 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.2716 | LD50, mol/kg |
| Fish Toxicity | 0.8865 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3980 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 01/09/2008 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 01/09/2008 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 01/09/2008 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.01* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.01* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.01* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 01/09/2008 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 01/09/2008 | |
| Macadamias | 0120070 | European Union | 0.01* | 01/09/2008 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 01/09/2008 | |
| Pistachios | 0120100 | European Union | 0.01* | 01/09/2008 | |
| Walnuts | 0120110 | European Union | 0.01* | 01/09/2008 | |
| Others (2) | 0120990 | European Union | 0.01* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Functional and Catalytic Characterization of the Detoxifying Enzyme Haloalkane Dehalogenase from Rhizobium leguminosarum. | Protein Pept Lett | 2017 | 28641560 |
| Enhancement of Shelf Life of Button Mushroom, Agaricus bisporus (HigherBasidiomycetes) by Fumigant Application of Lippia alba Essential Oil. | Int J Med Mushrooms | 2015 | 25746409 |
| Assessment of the reproductive and developmental toxicity of pesticide/fertilizermixtures based on confirmed pesticide contamination in California and Iowagroundwater. | Fundam Appl Toxicol | 1994 May | 8056207 |
| Economic costs of misinforming about risk: the EDB scare and the media. | Risk Anal | 1988 Jun | 3045904 |
| Rapid determination of fumigant and industrial chemical residues in food. | J Assoc Off Anal Chem | 1988 Jul-Aug | 3417594 |
| Determination of fumigants in cereals and cereal products by capillary gaschromatography. | Z Lebensm Unters Forsch | 1988 Aug | 3223092 |
| Contaminant and nutrient concentrations of natural ingredient rat and mouse diet used in chemical toxicology studies. | Fundam Appl Toxicol | 1987 Aug | 3653575 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Methyltransferase activity
- Specific Function:
- Involved in the cellular defense against the biological effects of O6-methylguanine (O6-MeG) in DNA. Repairs alkylated guanine in DNA by stoichiometrically transferring the alkyl group at the O-6 position to a cysteine residue in the enzyme. This is a suicide reaction: the enzyme is irreversibly inactivated.
- Gene Name:
- MGMT
- Uniprot ID:
- P16455
- Molecular Weight:
- 21645.83 Da
References
- Liu L, Pegg AE, Williams KM, Guengerich FP: Paradoxical enhancement of the toxicity of 1,2-dibromoethane by O6-alkylguanine-DNA alkyltransferase. J Biol Chem. 2002 Oct 4;277(40):37920-8. Epub 2002 Jul 31. [12151404 ]
- General Function:
- Toxic substance binding
- Specific Function:
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
- Gene Name:
- ALB
- Uniprot ID:
- P02768
- Molecular Weight:
- 69365.94 Da
- Mechanism of Action:
- 1,2-Dibromoethane binds to serum albumin.
References
- Kaphalia BS, Ansari GA: Covalent binding of ethylene dibromide and its metabolites to albumin. Toxicol Lett. 1992 Sep;62(2-3):221-30. [1412507 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]