2,4,6-Tribromophenol
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Basic Info
| Common Name | 2,4,6-Tribromophenol(F05521) |
| 2D Structure | |
| Description | 2,4,6-Tribromophenol is found in crustaceans. 2,4,6-Tribromophenol is isolated from molluscs and crustaceans. 2,4,6-Tribromophenol is a flavour component of seafood, imparts an intense shrimp-like flavour. 2,4,6-Tribromophenol belongs to the family of Bromobenzenes. These are organic compounds containing a chlorine atom attached to a benzene ring. |
| FRCD ID | F05521 |
| CAS Number | 118-79-6 |
| PubChem CID | 1483 |
| Formula | C6H3Br3O |
| IUPAC Name | 2,4,6-tribromophenol |
| InChI Key | BSWWXRFVMJHFBN-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H |
| Canonical SMILES | C1=C(C=C(C(=C1Br)O)Br)Br |
| Isomeric SMILES | C1=C(C=C(C(=C1Br)O)Br)Br |
| Synonyms |
Bromkal pur 3
2,4,6-tribromophenol
118-79-6
Tribromophenol
Bromol
Xeroform
Phenol, 2,4,6-tribromo-
Flammex 3BP
C6H3Br3O
TA 10
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Halophenols |
| Intermediate Tree Nodes | Bromophenols |
| Direct Parent | P-bromophenols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | 4-bromophenol - 2-bromophenol - Halobenzene - Bromobenzene - Monocyclic benzene moiety - Aryl halide - Aryl bromide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organobromide - Organohalogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as p-bromophenols. These are bromophenols carrying a iodine at the C4 position of the benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 330.801 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 108 |
| Monoisotopic Mass | 327.773 |
| Exact Mass | 329.771 |
| XLogP | 4.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| 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+ | 0.9585 |
| Human Intestinal Absorption | HIA+ | 0.9903 |
| Caco-2 Permeability | Caco2+ | 0.8828 |
| P-glycoprotein Substrate | Non-substrate | 0.8084 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9640 |
| Non-inhibitor | 0.9892 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8667 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7986 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8179 |
| CYP450 2D6 Substrate | Non-substrate | 0.8231 |
| CYP450 3A4 Substrate | Non-substrate | 0.7125 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8452 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5000 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9386 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5634 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8567 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6483 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8638 |
| Non-inhibitor | 0.9353 | |
| AMES Toxicity | Non AMES toxic | 0.9486 |
| Carcinogens | Non-carcinogens | 0.8050 |
| Fish Toxicity | High FHMT | 0.9032 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9939 |
| Honey Bee Toxicity | High HBT | 0.7984 |
| Biodegradation | Not ready biodegradable | 0.8098 |
| Acute Oral Toxicity | III | 0.5271 |
| Carcinogenicity (Three-class) | Non-required | 0.5232 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.1485 | LogS |
| Caco-2 Permeability | 1.8089 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5362 | LD50, mol/kg |
| Fish Toxicity | 0.6309 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.4699 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Evaluation of the effect of brominated flame retardants on hemoglobin oxidation and hemolysis in human erythrocytes. | Food Chem Toxicol | 2017 Nov | 28893619 |
| Recycling of plastic waste: Screening for brominated flame retardants (BFRs). | Waste Manag | 2017 Nov | 28869101 |
| Induced production of brominated aromatic compounds in the alga Ceramium tenuicorne. | Environ Sci Pollut Res Int | 2015 Nov | 26178826 |
| Tribromophenol and pentachlorophenol uptake from sawdust to horticulturalproducts. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2009Oct | 19701836 |
| Contrasting the seasonal variability of halogenated natural products andanthropogenic hexachlorocyclohexanes in the southern Norwegian atmosphere. | Arch Environ Contam Toxicol | 2008 Nov | 18330614 |
| Determination of halophenolic wood preservant traces in milk using headspacesolid-phase microextraction and gas chromatography-mass spectrometry. | J Chromatogr A | 2008 Dec 26 | 19027907 |
| Halogenated natural products in five species of Antarctic sponges: compounds withPOP-like properties? | Environ Sci Technol | 2005 Jun 1 | 15984761 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Identical protein binding
- Specific Function:
- Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
- Gene Name:
- TTR
- Uniprot ID:
- P02766
- Molecular Weight:
- 15886.88 Da
References
- Meerts IA, van Zanden JJ, Luijks EA, van Leeuwen-Bol I, Marsh G, Jakobsson E, Bergman A, Brouwer A: Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro. Toxicol Sci. 2000 Jul;56(1):95-104. [10869457 ]
- 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
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]