Hexabromocyclododecane
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Hexabromocyclododecane(F04348) |
| 2D Structure | |
| Description | Hexabromocyclododecane is an organobromide compound. It is a brominated flame retardant used in extruded (XPS) and expanded (EPS) polystyrene foam that is used as thermal insulation in the building industry. Hexabromocyclododecane is also a persistent organic pollutant, thus its use is controversial. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (L625, 1082) |
| FRCD ID | F04348 |
| CAS Number | 25637-99-4 |
| PubChem CID | 33121 |
| Formula | C12H18Br6 |
| IUPAC Name | 1,3,5,7,9,11-hexabromocyclododecane |
| InChI Key | LEOCKULGXOQRTQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H18Br6/c13-7-1-8(14)3-10(16)5-12(18)6-11(17)4-9(15)2-7/h7-12H,1-6H2 |
| Canonical SMILES | C1C(CC(CC(CC(CC(CC1Br)Br)Br)Br)Br)Br |
| Isomeric SMILES | C1C(CC(CC(CC(CC(CC1Br)Br)Br)Br)Br)Br |
| Synonyms |
DTXSID8025383
1,3,5,7,9,11-hexabromocyclododecane
Cyclododecane, hexabromo-
CCRIS 4821
AC1L1OZW
SCHEMBL942763
EINECS 247-148-4
Hexabromocyclododecane, mixed isomers
LS-1082
|
| Classifies |
Pollutant
|
| 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 homomonocyclic compounds |
| Substituents | Hydrocarbon derivative - Organobromide - Alkyl halide - Alkyl bromide - Aliphatic homomonocyclic 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 | 641.7 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 151 |
| Monoisotopic Mass | 635.651 |
| Exact Mass | 641.645 |
| XLogP | 7.1 |
| 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+ | 0.9831 |
| Human Intestinal Absorption | HIA+ | 0.9937 |
| Caco-2 Permeability | Caco2+ | 0.7095 |
| P-glycoprotein Substrate | Non-substrate | 0.8634 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9617 |
| Non-inhibitor | 0.9036 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8782 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7090 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.9005 |
| CYP450 2D6 Substrate | Non-substrate | 0.7066 |
| CYP450 3A4 Substrate | Non-substrate | 0.7620 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6041 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8185 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9553 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7927 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9639 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8412 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9382 |
| Non-inhibitor | 0.9436 | |
| AMES Toxicity | Non AMES toxic | 0.7097 |
| Carcinogens | Non-carcinogens | 0.5688 |
| Fish Toxicity | High FHMT | 0.8943 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9985 |
| Honey Bee Toxicity | High HBT | 0.8354 |
| Biodegradation | Not ready biodegradable | 0.9740 |
| Acute Oral Toxicity | III | 0.4341 |
| Carcinogenicity (Three-class) | Non-required | 0.5204 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4871 | LogS |
| Caco-2 Permeability | 1.5983 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1056 | LD50, mol/kg |
| Fish Toxicity | 0.8275 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0329 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Brominated flame retardants and toxic elements in the meat and liver of red deer (Cervus elaphus), wild boar (Sus scrofa), and moose (Alces alces) from Latvian wildlife. | Sci Total Environ | 2018 Apr 15 | 29202283 |
| Linking toxicity profiles to pollutants in sludge and sediments. | J Hazard Mater | 2017 Jan 5 | 27694046 |
| Lethal and Sublethal Toxicity Comparison of BFRs to Three Marine Planktonic Copepods: Effects on Survival, Metabolism and Ingestion. | PLoS One | 2016 | 26824601 |
| Human dietary intake of organohalogen contaminants at e-waste recycling sites in Eastern China. | Environ Int | 2015 Jan | 25454238 |
| Food risk assessment for perfluoroalkyl acids and brominated flame retardants in the French population: results from the second French total diet study. | Sci Total Environ | 2014 Sep 1 | 24529894 |
| Halogenated contaminants in farmed salmon, trout, tilapia, pangasius, and shrimp. | Environ Sci Technol | 2009 Jun 1 | 19569323 |
| Halogenated persistent organic pollutants in Scottish deep water fish. | J Environ Monit | 2009 Feb | 19212601 |
| Fourth WHO-coordinated survey of human milk for persistent organic pollutants (POPs): Belgian results. | Chemosphere | 2008 Oct | 18718632 |
| Brominated and chlorinated dioxins, PCBs and brominated flame retardants in Scottish shellfish: methodology, occurrence and human dietary exposure. | Mol Nutr Food Res | 2008 Feb | 18186102 |
| Toxic effects of brominated flame retardants in man and in wildlife. | Environ Int | 2003 Sep | 12850100 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
- Gene Name:
- PGR
- Uniprot ID:
- P06401
- Molecular Weight:
- 98979.96 Da
References
- Suzuki G, Tue NM, Malarvannan G, Sudaryanto A, Takahashi S, Tanabe S, Sakai S, Brouwer A, Uramaru N, Kitamura S, Takigami H: Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays. Environ Sci Technol. 2013 Mar 19;47(6):2898-908. doi: 10.1021/es304691a. Epub 2013 Mar 1. [23398518 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Isoform Alpha-1: Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.Isoform Alpha-2: Does not bind thyroid hormone and functions as a weak dominant negative inhibitor of thyroid hormone action.
- Gene Name:
- THRA
- Uniprot ID:
- P10827
- Molecular Weight:
- 54815.055 Da
References
- Yamada-Okabe T, Sakai H, Kashima Y, Yamada-Okabe H: Modulation at a cellular level of the thyroid hormone receptor-mediated gene expression by 1,2,5,6,9,10-hexabromocyclododecane (HBCD), 4,4'-diiodobiphenyl (DIB), and nitrofen (NIP). Toxicol Lett. 2005 Jan 15;155(1):127-33. [15585367 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Suzuki G, Tue NM, Malarvannan G, Sudaryanto A, Takahashi S, Tanabe S, Sakai S, Brouwer A, Uramaru N, Kitamura S, Takigami H: Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays. Environ Sci Technol. 2013 Mar 19;47(6):2898-908. doi: 10.1021/es304691a. Epub 2013 Mar 1. [23398518 ]