2,2',4,4',5,5'-Hexabromodiphenyl ether (BioDeep_00000012105)
Secondary id: BioDeep_00001868637
human metabolite
代谢物信息卡片
1,2,4-tribromo-5-(2,4,5-tribromophenoxy)benzene
化学式: C12H4Br6O (637.5362293999999)
中文名称: 2,2,4,4,5,5-六溴联苯醚
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: BrC1=CC(Br)=C(Br)C=C1OC1=CC(Br)=C(Br)C=C1Br
InChI: InChI=1S/C12H4Br6O/c13-5-1-9(17)11(3-7(5)15)19-12-4-8(16)6(14)2-10(12)18/h1-4H
描述信息
2,2,4,4,5,5-Hexabromodiphenyl ether is classified as a Food Contaminant (code WG) in the DFC.
Classified as a Food Contaminant (code WG) in the DFC
同义名列表
12 个代谢物同义名
1,2,4-tribromo-5-(2,4,5-tribromophenoxy)benzene; 2,2,4,4,5,5-Hexabrominated diphenyl ether; 1,1-Oxybis[2,4,5-tribromo]benzene, 9ci; 2,2,4,4,5,5-Brominated diphenyl ether; 2,2,4,4,5,5-Hexabromodiphenyl ether; 1,1-Oxybis(2,4,5-tribromobenzene); 1,1-Oxybis(2,4,5-tribromo-benzene; Hexabrominated diphenyl ether 153; 2,2,4,4,5,5-HexaBDE; PBDE 153; BDE-153; BDE 153
数据库引用编号
13 个数据库交叉引用编号
- ChEBI: CHEBI:81534
- KEGG: C18137
- PubChem: 155166
- HMDB: HMDB0037525
- Metlin: METLIN72055
- ChEMBL: CHEMBL1568307
- foodb: FDB016606
- chemspider: 136695
- CAS: 68631-49-2
- PMhub: MS000026391
- PubChem: 96024354
- NIKKAJI: J201.390H
- RefMet: 2,2',4,4',5,5'-Hexabromodiphenyl ether
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Julia R Varshavsky, Saunak Sen, Joshua F Robinson, Sabrina Crispo Smith, Julie Frankenfield, Yunzhu Wang, Greg Yeh, June-Soo Park, Susan J Fisher, Tracey J Woodruff. Racial/ethnic and geographic differences in polybrominated diphenyl ether (PBDE) levels across maternal, placental, and fetal tissues during mid-gestation.
Scientific reports.
2020 07; 10(1):12247. doi:
10.1038/s41598-020-69067-y. [PMID: 32699379] - Ling-Chuan Guo, Shengbing Yu, De Wu, Jinxu Huang, Tao Liu, Jianpeng Xiao, Weixiong Huang, Yanhong Gao, Xing Li, Weilin Zeng, Shannon Rutherford, Wenjun Ma, Yonghui Zhang, Lifeng Lin. Disruption of thyroid hormone regulated proteins and gene expression by polychlorinated biphenyls, polybrominated diphenyl ethers and new flame retardants in residents of an e-waste region.
Environmental pollution (Barking, Essex : 1987).
2019 Nov; 254(Pt B):112925. doi:
10.1016/j.envpol.2019.07.093. [PMID: 31454572] - Beata Drobná, Anna Fabišiková, Kamil Čonka, František Gago, Petra Oravcová, Soňa Wimmerová, Marina Oktapodas Feiler, Eva Šovčíková. PBDE serum concentration and preschool maturity of children from Slovakia.
Chemosphere.
2019 Oct; 233(?):387-395. doi:
10.1016/j.chemosphere.2019.05.284. [PMID: 31176902] - Noriko Kanaya, Lauren Bernal, Gregory Chang, Takuro Yamamoto, Duc Nguyen, Yuan-Zhong Wang, June-Soo Park, Charles Warden, Jinhui Wang, Xiwei Wu, Timothy Synold, Michele Rakoff, Susan L Neuhausen, Shiuan Chen. Molecular Mechanisms of Polybrominated Diphenyl Ethers (BDE-47, BDE-100, and BDE-153) in Human Breast Cancer Cells and Patient-Derived Xenografts.
Toxicological sciences : an official journal of the Society of Toxicology.
2019 06; 169(2):380-398. doi:
10.1093/toxsci/kfz054. [PMID: 30796839] - Li-Jung Kuo, Sara E Cade, Valerie Cullinan, Irvin R Schultz. Polybrominated diphenyl ethers (PBDEs) in plasma from E-waste recyclers, outdoor and indoor workers in the Puget Sound, WA region.
Chemosphere.
2019 Mar; 219(?):209-216. doi:
10.1016/j.chemosphere.2018.12.006. [PMID: 30543955] - Juan Pedro Arrebola, Juan José Ramos, Mónica Bartolomé, Marta Esteban, Olga Huetos, Ana I Cañas, Ana López-Herranz, Eva Calvo, Beatriz Pérez-Gómez, Argelia Castaño. Associations of multiple exposures to persistent toxic substances with the risk of hyperuricemia and subclinical uric acid levels in BIOAMBIENT.ES study.
Environment international.
2019 02; 123(?):512-521. doi:
10.1016/j.envint.2018.12.030. [PMID: 30622076] - Whitney J Cowell, Andreas Sjödin, Richard Jones, Ya Wang, Shuang Wang, Julie B Herbstman. Temporal trends and developmental patterns of plasma polybrominated diphenyl ether concentrations over a 15-year period between 1998 and 2013.
Journal of exposure science & environmental epidemiology.
2019 01; 29(1):49-60. doi:
10.1038/s41370-018-0031-3. [PMID: 29618764] - Emily Parry, Ami R Zota, June-Soo Park, Tracey J Woodruff. Polybrominated diphenyl ethers (PBDEs) and hydroxylated PBDE metabolites (OH-PBDEs): A six-year temporal trend in Northern California pregnant women.
Chemosphere.
2018 Mar; 195(?):777-783. doi:
10.1016/j.chemosphere.2017.12.065. [PMID: 29289024] - L Bramwell, S Harrad, M Abou-Elwafa Abdallah, C Rauert, M Rose, A Fernandes, T Pless-Mulloli. Predictors of human PBDE body burdens for a UK cohort.
Chemosphere.
2017 Dec; 189(?):186-197. doi:
10.1016/j.chemosphere.2017.08.062. [PMID: 28965056] - Satori A Marchitti, Suzanne E Fenton, Pauline Mendola, John F Kenneke, Erin P Hines. Polybrominated Diphenyl Ethers in Human Milk and Serum from the U.S. EPA MAMA Study: Modeled Predictions of Infant Exposure and Considerations for Risk Assessment.
Environmental health perspectives.
2017 04; 125(4):706-713. doi:
10.1289/ehp332. [PMID: 27405099] - Helena Bjermo, Marie Aune, Tatiana Cantillana, Anders Glynn, P Monica Lind, Peter Ridefelt, Per Ola Darnerud. Serum levels of brominated flame retardants (BFRs: PBDE, HBCD) and influence of dietary factors in a population-based study on Swedish adults.
Chemosphere.
2017 Jan; 167(?):485-491. doi:
10.1016/j.chemosphere.2016.10.008. [PMID: 27750173] - Melissa M Smarr, Katherine L Grantz, Cuilin Zhang, Rajeshwari Sundaram, José M Maisog, Dana Boyd Barr, Germaine M Buck Louis. Persistent organic pollutants and pregnancy complications.
The Science of the total environment.
2016 May; 551-552(?):285-91. doi:
10.1016/j.scitotenv.2016.02.030. [PMID: 26878640] - Jongchul Kim, Min-Hui Son, Eun-Su Shin, Sung-Deuk Choi, Yoon-Seok Chang. Occurrence of Dechlorane compounds and polybrominated diphenyl ethers (PBDEs) in the Korean general population.
Environmental pollution (Barking, Essex : 1987).
2016 May; 212(?):330-336. doi:
10.1016/j.envpol.2016.01.085. [PMID: 26854703] - Ruiling Liu, David O Nelson, Susan Hurley, Myrto Petreas, June-Soo Park, Yunzhu Wang, Weihong Guo, Leslie Bernstein, Andrew Hertz, Peggy Reynolds. Association between Serum Polybrominated Diphenyl Ether Levels and Residential Proximity to Solid-Waste Facilities.
Environmental science & technology.
2016 Apr; 50(7):3945-53. doi:
10.1021/acs.est.5b04715. [PMID: 26906616] - Marie Lynn Miranda, Rebecca Anthopolos, Amy Wolkin, Heather M Stapleton. Associations of birth outcomes with maternal polybrominated diphenyl ethers and thyroid hormones during pregnancy.
Environment international.
2015 Dec; 85(?):244-53. doi:
10.1016/j.envint.2015.09.015. [PMID: 26431883] - Enrique Cequier, Rosa Maria Marcé, Georg Becher, Cathrine Thomsen. Comparing human exposure to emerging and legacy flame retardants from the indoor environment and diet with concentrations measured in serum.
Environment international.
2015 Jan; 74(?):54-9. doi:
10.1016/j.envint.2014.10.003. [PMID: 25454220] - William T Route, Cheryl R Dykstra, Paul W Rasmussen, Rebecca L Key, Michael W Meyer, John Mathew. Patterns and trends in brominated flame retardants in bald eagle nestlings from the upper midwestern United States.
Environmental science & technology.
2014 Nov; 48(21):12516-24. doi:
10.1021/es501859a. [PMID: 25272197] - Robert J Letcher, Sarah C Marteinson, Kim J Fernie. Dietary exposure of American kestrels (Falco sparverius) to decabromodiphenyl ether (BDE-209) flame retardant: uptake, distribution, debromination and cytochrome P450 enzyme induction.
Environment international.
2014 Feb; 63(?):182-90. doi:
10.1016/j.envint.2013.11.010. [PMID: 24317224] - Gunnar Toft, Virissa Lenters, Roel Vermeulen, Dick Heederik, Cathrine Thomsen, Georg Becher, Aleksander Giwercman, Davide Bizzaro, Gian Carlo Manicardi, Marcello Spanò, Lars Rylander, Henning S Pedersen, Paweł Struciński, Valentyna Zviezdai, Jens Peter Bonde. Exposure to polybrominated diphenyl ethers and male reproductive function in Greenland, Poland and Ukraine.
Reproductive toxicology (Elmsford, N.Y.).
2014 Jan; 43(?):1-7. doi:
10.1016/j.reprotox.2013.10.002. [PMID: 24513925] - Kazuhiko Akutsu, Satoshi Takatori, Hiroyuki Nakazawa, Tsunehisa Makino. Detection of polybrominated diphenyl ethers in culture media and protein sources used for human in vitro fertilization.
Chemosphere.
2013 Aug; 92(7):864-9. doi:
10.1016/j.chemosphere.2013.04.087. [PMID: 23746364] - K Jakobsson, J Fång, M Athanasiadou, A Rignell-Hydbom, A Bergman. Polybrominated diphenyl ethers in maternal serum, umbilical cord serum, colostrum and mature breast milk. Insights from a pilot study and the literature.
Environment international.
2012 Oct; 47(?):121-30. doi:
10.1016/j.envint.2012.05.006. [PMID: 22819984] - Paula I Johnson, Larisa Altshul, Daniel W Cramer, Stacey A Missmer, Russ Hauser, John D Meeker. Serum and follicular fluid concentrations of polybrominated diphenyl ethers and in-vitro fertilization outcome.
Environment international.
2012 Sep; 45(?):9-14. doi:
10.1016/j.envint.2012.04.004. [PMID: 22572111] - Heather M Stapleton, Sarah Eagle, Andreas Sjödin, Thomas F Webster. Serum PBDEs in a North Carolina toddler cohort: associations with handwipes, house dust, and socioeconomic variables.
Environmental health perspectives.
2012 Jul; 120(7):1049-54. doi:
10.1289/ehp.1104802. [PMID: 22763040] - Erik Pacyniak, Bruno Hagenbuch, Curtis D Klaassen, Lois Lehman-McKeeman, Grace L Guo. Organic anion transporting polypeptides in the hepatic uptake of PBDE congeners in mice.
Toxicology and applied pharmacology.
2011 Nov; 257(1):23-31. doi:
10.1016/j.taap.2011.08.014. [PMID: 21884716] - G S Bondy, D Gaertner, W Cherry, E MacLellan, L Coady, D L Arnold, J Doucet, P R Rowsell. Brominated diphenyl ether (BDE) levels in liver, adipose, and milk from adult and juvenile rats exposed by gavage to the DE-71 technical mixture.
Environmental toxicology.
2011 Nov; 26(6):677-90. doi:
10.1002/tox.20603. [PMID: 20549633] - Riikka Airaksinen, Panu Rantakokko, Johan G Eriksson, Paul Blomstedt, Eero Kajantie, Hannu Kiviranta. Association between type 2 diabetes and exposure to persistent organic pollutants.
Diabetes care.
2011 Sep; 34(9):1972-9. doi:
10.2337/dc10-2303. [PMID: 21816981] - Ji-Sun Lim, Duk-Hee Lee, David R Jacobs. Association of brominated flame retardants with diabetes and metabolic syndrome in the U.S. population, 2003-2004.
Diabetes care.
2008 Sep; 31(9):1802-7. doi:
10.2337/dc08-0850. [PMID: 18559655] - Lisethe Meijer, Jana Weiss, Martin Van Velzen, Abraham Brouwer, Ake Bergman, Pieter J J Sauer. Serum concentrations of neutral and phenolic organohalogens in pregnant women and some of their infants in The Netherlands.
Environmental science & technology.
2008 May; 42(9):3428-33. doi:
10.1021/es702446p. [PMID: 18522129] - K Akutsu, S Takatori, S Nozawa, M Yoshiike, H Nakazawa, K Hayakawa, T Makino, T Iwamoto. Polybrominated diphenyl ethers in human serum and sperm quality.
Bulletin of environmental contamination and toxicology.
2008 Apr; 80(4):345-50. doi:
10.1007/s00128-008-9370-4. [PMID: 18320132] - Cathrine Thomsen, Helle K Knutsen, Veronica H Liane, May Frøshaug, Helen E Kvalem, Margaretha Haugen, Helle M Meltzer, Jan Alexander, Georg Becher. Consumption of fish from a contaminated lake strongly affects the concentrations of polybrominated diphenyl ethers and hexabromocyclododecane in serum.
Molecular nutrition & food research.
2008 Feb; 52(2):228-37. doi:
10.1002/mnfr.200700123. [PMID: 18186101] - Torkjel M Sandanger, Marc Sinotte, Pierre Dumas, Mario Marchand, Courtney D Sandau, Daria Pereg, Sylvie Bérubé, Jacques Brisson, Pierre Ayotte. Plasma concentrations of selected organobromine compounds and polychlorinated biphenyls in postmenopausal women of Québec, Canada.
Environmental health perspectives.
2007 Oct; 115(10):1429-34. doi:
10.1289/ehp.10303. [PMID: 17938731] - Xinghua Qiu, Minerva Mercado-Feliciano, Robert M Bigsby, Ronald A Hites. Measurement of polybrominated diphenyl ethers and metabolites in mouse plasma after exposure to a commercial pentabromodiphenyl ether mixture.
Environmental health perspectives.
2007 Jul; 115(7):1052-8. doi:
10.1289/ehp.10011. [PMID: 17637922] - Per Ola Darnerud, Marie Aune, Lotta Larsson, Sara Hallgren. Plasma PBDE and thyroxine levels in rats exposed to Bromkal or BDE-47.
Chemosphere.
2007 Apr; 67(9):S386-92. doi:
10.1016/j.chemosphere.2006.05.133. [PMID: 17257644] - Ana Labandeira, Ethel Eljarrat, Damià Barceló. Congener distribution of polybrominated diphenyl ethers in feral carp (Cyprinus carpio) from the Llobregat River, Spain.
Environmental pollution (Barking, Essex : 1987).
2007 Mar; 146(1):188-95. doi:
10.1016/j.envpol.2006.04.037. [PMID: 17010488] - Stefan Voorspoels, Adrian Covaci, Peter Lepom, Veerle L B Jaspers, Paul Schepens. Levels and distribution of polybrominated diphenyl ethers in various tissues of birds of prey.
Environmental pollution (Barking, Essex : 1987).
2006 Nov; 144(1):218-27. doi:
10.1016/j.envpol.2005.12.027. [PMID: 16530311] - Daniele F Staskal, Heldur Hakk, Daniel Bauer, Janet J Diliberto, Linda S Birnbaum. Toxicokinetics of polybrominated diphenyl ether congeners 47, 99, 100, and 153 in mice.
Toxicological sciences : an official journal of the Society of Toxicology.
2006 Nov; 94(1):28-37. doi:
10.1093/toxsci/kfl091. [PMID: 16936226] - J M Sanders, E H Lebetkin, L-J Chen, L T Burka. Disposition of 2,2',4,4',5,5'-hexabromodiphenyl ether (BDE153) and its interaction with other polybrominated diphenyl ethers (PBDEs) in rodents.
Xenobiotica; the fate of foreign compounds in biological systems.
2006 Sep; 36(9):824-37. doi:
10.1080/00498250600815906. [PMID: 16971346] - Timo Hamers, Jorke H Kamstra, Edwin Sonneveld, Albertinka J Murk, Monique H A Kester, Patrik L Andersson, Juliette Legler, Abraham Brouwer. In vitro profiling of the endocrine-disrupting potency of brominated flame retardants.
Toxicological sciences : an official journal of the Society of Toxicology.
2006 Jul; 92(1):157-73. doi:
10.1093/toxsci/kfj187. [PMID: 16601080] - Britta Fängström, Lotta Hovander, Anders Bignert, Ioannis Athanassiadis, Linda Linderholm, Philippe Grandjean, Pál Weihe, Ake Bergman. Concentrations of polybrominated diphenyl ethers, polychlonnated biphenyls, and polychlorobiphenylols in serum from pregnant Faroese women and their children 7 years later.
Environmental science & technology.
2005 Dec; 39(24):9457-63. doi:
10.1021/es0513032. [PMID: 16475322] - Silke Rupp, Jörg W Metzger. Brominated-chlorinated diphenyl ethers formed by thermolysis of polybrominated diphenyl ethers at low temperatures.
Chemosphere.
2005 Sep; 60(11):1644-51. doi:
10.1016/j.chemosphere.2005.02.038. [PMID: 16083771] - Kiyohiko Watanabe, Kurunthachalam Senthilkumar, Shigeki Masunaga, Takumi Takasuga, Naomasa Iseki, Masatoshi Morita. Brominated organic contaminants in the liver and egg of the common cormorants (Phalacrocorax carbo) from Japan.
Environmental science & technology.
2004 Aug; 38(15):4071-7. doi:
10.1021/es0307221. [PMID: 15352443] - Annika Smeds, Pekka Saukko. Brominated flame retardants and phenolic endocrine disrupters in Finnish human adipose tissue.
Chemosphere.
2003 Dec; 53(9):1123-30. doi:
10.1016/s0045-6535(03)00589-7. [PMID: 14512116] - Jae-Won Choi, T Susumu Fujimaki, Kimiyoshi Kitamura, Shunji Hashimoto, Hiroyasu Ito, Noriyuki Suzuki, Shin-ichi Sakai, Masatoshi Morita. Polybrominated dibenzo-p-dioxins, dibenzofurans, and diphenyl ethers in Japanese human adipose tissue.
Environmental science & technology.
2003 Mar; 37(5):817-21. doi:
10.1021/es0258780. [PMID: 12666907] - Cathrine Thomsen, Elsa Lundanes, Georg Becher. Brominated flame retardants in archived serum samples from Norway: a study on temporal trends and the role of age.
Environmental science & technology.
2002 Apr; 36(7):1414-8. doi:
10.1021/es0102282. [PMID: 11999045] - A Sjödin, D G Patterson, A Bergman. Brominated flame retardants in serum from U.S. blood donors.
Environmental science & technology.
2001 Oct; 35(19):3830-3. doi:
10.1021/es010815n. [PMID: 11642440] - C Thomsen, E Lundanes, G Becher. Brominated flame retardants in plasma samples from three different occupational groups in Norway.
Journal of environmental monitoring : JEM.
2001 Aug; 3(4):366-70. doi:
10.1039/b104304h. [PMID: 11523435]