2,3,7,8-Tetrachlorodibenzofuran (BioDeep_00000012079)

 

Secondary id: BioDeep_00001868151

human metabolite blood metabolite Industrial Pollutants Volatile Flavor Compounds


代谢物信息卡片


4,5,11,12-tetrachloro-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene

化学式: C12H4Cl4O (303.9016254)
中文名称: 2,4,7,8-四氯二苯并呋喃
谱图信息: 最多检出来源 Homo sapiens(blood) 87.5%

分子结构信息

SMILES: C1=C2C3=CC(=C(C=C3OC2=CC(=C1Cl)Cl)Cl)Cl
InChI: InChI=1S/C12H4Cl4O/c13-7-1-5-6-2-8(14)10(16)4-12(6)17-11(5)3-9(7)15/h1-4H

描述信息

D004785 - Environmental Pollutants

同义名列表

5 个代谢物同义名

4,5,11,12-tetrachloro-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene; 2,3,7,8-TETRACHLORODIBENZOFURAN; 2,3,7,8-TCDF; PCDF 83; 2,3,7,8-Tetrachlorodibenzofuran



数据库引用编号

11 个数据库交叉引用编号

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

  • Eiki Kimura, Go Suzuki, Naoto Uramaru, Masaki Kakeyama, Fumihiko Maekawa. Liver-specific decrease in Tff3 gene expression in infant mice perinatally exposed to 2,3,7,8-tetrabromodibenzofuran or 2,3,7,8-tetrachlorodibenzo-p-dioxin. Journal of applied toxicology : JAT. 2022 02; 42(2):305-317. doi: 10.1002/jat.4220. [PMID: 34254344]
  • Qing Liu, Limin Zhang, Erik L Allman, Troy D Hubbard, Iain A Murray, Fuhua Hao, Yuan Tian, Wei Gui, Robert G Nichols, Philip B Smith, Mallappa Anitha, Gary H Perdew, Andrew D Patterson. The aryl hydrocarbon receptor activates ceramide biosynthesis in mice contributing to hepatic lipogenesis. Toxicology. 2021 06; 458(?):152831. doi: 10.1016/j.tox.2021.152831. [PMID: 34097992]
  • Yuan Tian, Wei Gui, Bipin Rimal, Imhoi Koo, Philip B Smith, Robert G Nichols, Jingwei Cai, Qing Liu, Andrew D Patterson. Metabolic impact of persistent organic pollutants on gut microbiota. Gut microbes. 2020 11; 12(1):1-16. doi: 10.1080/19490976.2020.1848209. [PMID: 33295235]
  • Peihong Yuan, Manyuan Dong, Hehua Lei, Guangyong Xu, Gui Chen, Yuchen Song, Jianfeng Ma, Liming Cheng, Limin Zhang. Targeted metabolomics reveals that 2,3,7,8-tetrachlorodibenzofuran exposure induces hepatic steatosis in male mice. Environmental pollution (Barking, Essex : 1987). 2020 Apr; 259(?):113820. doi: 10.1016/j.envpol.2019.113820. [PMID: 31918130]
  • Doha Yahia, Yasmin O El-Amir, Doaa S Abd El-Maguid, Eman E Elsharkawy. Co-administration of glutathione alleviates the toxic effects of 2,3,7,8 TCDF on the DNA integrity of sperm and in the testes of mice. Environmental science and pollution research international. 2018 Nov; 25(32):32572-32581. doi: 10.1007/s11356-018-3259-5. [PMID: 30242650]
  • Kelly A Fader, Rance Nault, Mathew P Kirby, Gena Markous, Jason Matthews, Timothy R Zacharewski. Convergence of hepcidin deficiency, systemic iron overloading, heme accumulation, and REV-ERBα/β activation in aryl hydrocarbon receptor-elicited hepatotoxicity. Toxicology and applied pharmacology. 2017 04; 321(?):1-17. doi: 10.1016/j.taap.2017.02.006. [PMID: 28213091]
  • Jung-Wei Chang, Hsiu-Ling Chen, Huey-Jen Su, Ching-Chang Lee. Abdominal Obesity and Insulin Resistance in People Exposed to Moderate-to-High Levels of Dioxin. PloS one. 2016; 11(1):e0145818. doi: 10.1371/journal.pone.0145818. [PMID: 26752053]
  • Limin Zhang, Emmanuel Hatzakis, Robert G Nichols, Ruixin Hao, Jared Correll, Philip B Smith, Christopher R Chiaro, Gary H Perdew, Andrew D Patterson. Metabolomics Reveals that Aryl Hydrocarbon Receptor Activation by Environmental Chemicals Induces Systemic Metabolic Dysfunction in Mice. Environmental science & technology. 2015 Jul; 49(13):8067-77. doi: 10.1021/acs.est.5b01389. [PMID: 26023891]
  • Karin I van Ede, Konrad P J Gaisch, Martin van den Berg, Majorie B M van Duursen. Differential relative effect potencies of some dioxin-like compounds in human peripheral blood lymphocytes and murine splenic cells. Toxicology letters. 2014 Apr; 226(1):43-52. doi: 10.1016/j.toxlet.2014.01.026. [PMID: 24472611]
  • Li-Feng Yu, Wen-Xia Wei, Ya-Jing Tian, Guang-Long Wu, Pei-Zhong Li, Dan Zhao. [Analysis of characteristics of dioxin contamination in the chlor-alkali site that uses graphite anode for production]. Huan jing ke xue= Huanjing kexue. 2012 Jun; 33(6):2000-5. doi: ". [PMID: 22946188]
  • Maria Maddalena Storelli, Grazia Barone, Arianna Storelli, Giuseppe Onofrio Marcotrigiano. Levels and congener profiles of PCBs and PCDD/Fs in blue shark (Prionace glauca) liver from the South-Eastern Mediterranean Sea (Italy). Chemosphere. 2011 Jan; 82(1):37-42. doi: 10.1016/j.chemosphere.2010.10.014. [PMID: 20980044]
  • Alfred Franzblau, Elizabeth Hedgeman, Olivier Jolliet, Kristine Knutson, Tim Towey, Qixuan Chen, Biling Hong, Peter Adriaens, Avery Demond, David H Garabrant, Brenda W Gillespie, James Lepkowski. Case report: the University of Michigan dioxin exposure study: a follow-up investigation of a case with high serum concentration of 2,3,4,7,8-pentachlorodibenzofuran. Environmental health perspectives. 2010 Sep; 118(9):1313-7. doi: 10.1289/ehp.0901723. [PMID: 20813655]
  • Elizabeth Hedgeman, Qixuan Chen, Biling Hong, Chiung-Wen Chang, Kristen Olson, Kathleen Ladronka, Barbara Ward, Peter Adriaens, Avery Demond, Brenda W Gillespie, James Lepkowski, Alfred Franzblau, David H Garabrant. The University of Michigan Dioxin Exposure Study: population survey results and serum concentrations for polychlorinated dioxins, furans, and biphenyls. Environmental health perspectives. 2009 May; 117(5):811-7. doi: 10.1289/ehp.11780. [PMID: 19479026]
  • Matthew J Zwiernik, Jeremy N Moore, Jong Seong Khim, Lisa L Williams, Denise P Kay, Steve Bursian, Lesa L Aylward, John P Giesy. Nondestructive scat sampling in assessment of mink (Mustela vison) exposed to polychlorinated dibenzofurans (PCDFs). Archives of environmental contamination and toxicology. 2008 Oct; 55(3):529-37. doi: 10.1007/s00244-007-9131-0. [PMID: 18227958]
  • Ismet Cok, Menekse Keski Donmez, M Hakan Satiroğlu, Batu Aydinuraz, Bernhard Henkelmann, Heqing Shen, Jarmila Kotalik, Karl-Werner Schramm. Concentrations of polychlorinated dibenzo-p-dioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and dioxin-like PCBs in adipose tissue of infertile men. Archives of environmental contamination and toxicology. 2008 Jul; 55(1):143-52. doi: 10.1007/s00244-007-9094-1. [PMID: 18166985]
  • Alhaji N'Jai, Darrell R Boverhof, Edward Dere, Lyle D Burgoon, Ying S Tan, J Craig Rowlands, Robert A Budinsky, Kenneth E Stebbins, Timothy R Zacharewski. Comparative temporal toxicogenomic analysis of TCDD- and TCDF-mediated hepatic effects in immature female C57BL/6 mice. Toxicological sciences : an official journal of the Society of Toxicology. 2008 Jun; 103(2):285-97. doi: 10.1093/toxsci/kfn053. [PMID: 18343893]
  • Shu Zhang, Craig Rowlands, Stephen Safe. Ligand-dependent interactions of the Ah receptor with coactivators in a mammalian two-hybrid assay. Toxicology and applied pharmacology. 2008 Mar; 227(2):196-206. doi: 10.1016/j.taap.2007.10.019. [PMID: 18048071]
  • Sonomi Nakajima, Yasuaki Saijo, Shizue Kato, Seiko Sasaki, Akiko Uno, Nobuo Kanagami, Hironori Hirakawa, Tsuguhide Hori, Kazuhiro Tobiishi, Takashi Todaka, Yuji Nakamura, Satoko Yanagiya, Yasuhito Sengoku, Takao Iida, Fumihiro Sata, Reiko Kishi. Effects of prenatal exposure to polychlorinated biphenyls and dioxins on mental and motor development in Japanese children at 6 months of age. Environmental health perspectives. 2006 May; 114(5):773-8. doi: 10.1289/ehp.8614. [PMID: 16675436]
  • Dorothea F K Rawn, Donald S Forsyth, John J Ryan, Kenneth Breakell, Victor Verigin, Helen Nicolidakis, Stephen Hayward, Patrick Laffey, Henry B S Conacher. PCB, PCDD and PCDF residues in fin and non-fin fish products from the Canadian retail market 2002. The Science of the total environment. 2006 Apr; 359(1-3):101-10. doi: 10.1016/j.scitotenv.2005.04.021. [PMID: 15913708]
  • Kevin M Crofton, Elena S Craft, Joan M Hedge, Chris Gennings, Jane E Simmons, Richard A Carchman, W Hans Carter, Michael J DeVito. Thyroid-hormone-disrupting chemicals: evidence for dose-dependent additivity or synergism. Environmental health perspectives. 2005 Nov; 113(11):1549-54. doi: 10.1289/ehp.8195. [PMID: 16263510]
  • Esteban Abad, Karell Martínez, Josep Caixach, Josep Rivera. Polychlorinated dibenzo-p-dioxin/polychlorinated dibenzofuran releases into the atmosphere from the use of secondary fuels in cement kilns during clinker formation. Environmental science & technology. 2004 Sep; 38(18):4734-8. doi: 10.1021/es049641a. [PMID: 15487780]
  • F Peter Guengerich, Martha V Martin, W Andrew McCormick, Linh P Nguyen, Edward Glover, Christopher A Bradfield. Aryl hydrocarbon receptor response to indigoids in vitro and in vivo. Archives of biochemistry and biophysics. 2004 Mar; 423(2):309-16. doi: 10.1016/j.abb.2004.01.002. [PMID: 15001395]
  • Shannon Mala Bard, Susan M Bello, Mark E Hahn, John J Stegeman. Expression of P-glycoprotein in killifish (Fundulus heteroclitus) exposed to environmental xenobiotics. Aquatic toxicology (Amsterdam, Netherlands). 2002 Sep; 59(3-4):237-51. doi: 10.1016/s0166-445x(01)00256-9. [PMID: 12127740]
  • C Y Chen, J T Hamm, J R Hass, L S Birnbaum. Disposition of polychlorinated dibenzo-p-dioxins, dibenzofurans, and non-ortho polychlorinated biphenyls in pregnant long evans rats and the transfer to offspring. Toxicology and applied pharmacology. 2001 Jun; 173(2):65-88. doi: 10.1006/taap.2001.9143. [PMID: 11384209]
  • K Morita, M Ogata, T Hasegawa. Chlorophyll derived from Chlorella inhibits dioxin absorption from the gastrointestinal tract and accelerates dioxin excretion in rats. Environmental health perspectives. 2001 Mar; 109(3):289-94. doi: 10.1289/ehp.01109289. [PMID: 11333191]
  • S M Bello, D G Franks, J J Stegeman, M E Hahn. Acquired resistance to Ah receptor agonists in a population of Atlantic killifish (Fundulus heteroclitus) inhabiting a marine superfund site: in vivo and in vitro studies on the inducibility of xenobiotic metabolizing enzymes. Toxicological sciences : an official journal of the Society of Toxicology. 2001 Mar; 60(1):77-91. doi: 10.1093/toxsci/60.1.77. [PMID: 11222875]
  • A R Steward, R Maslanka, J Pangrekar, S Kumar, H C Sikka. Disposition and metabolism of 2,3,7,8-tetrachlorodibenzofuran by rainbow trout (Oncorhynchus mykiss). Toxicology and applied pharmacology. 1996 Aug; 139(2):418-29. doi: 10.1006/taap.1996.0183. [PMID: 8806860]
  • A R Steward, R Maslanka, K G Stuart, S Kumar, H C Sikka. Disposition and metabolism of 2,3,7,8-tetrachlorodibenzofuran by channel catfish (Ictalurus punctatus). Toxicology and applied pharmacology. 1996 Aug; 139(2):430-6. doi: 10.1006/taap.1996.0184. [PMID: 8806861]
  • H Liu, S Safe. Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on insulin-induced responses in MCF-7 human breast cancer cells. Toxicology and applied pharmacology. 1996 Jun; 138(2):242-50. doi: 10.1006/taap.1996.0122. [PMID: 8658525]
  • K Chaloupka, M Santostefano, I S Goldfarb, G Liu, M J Myers, I B Tsyrolv, H V Gelboin, V Krishnan, S Safe. Aryl hydrocarbon (Ah) receptor-independent induction of Cyp1a2 gene expression by acenaphthylene and related compounds in B6C3F1 mice. Carcinogenesis. 1994 Dec; 15(12):2835-40. doi: 10.1093/carcin/15.12.2835. [PMID: 8001243]
  • M K McKinley, L B Kedderis, L S Birnbaum. The effect of pretreatment on the biliary excretion of 2,3,7,8-tetrachlorodibenzo-p-dioxin, 2,3,7,8-tetrachlorodibenzofuran, and 3,3',4,4'-tetrachlorobiphenyl in the rat. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1993 Nov; 21(4):425-32. doi: 10.1006/faat.1993.1118. [PMID: 8253296]
  • H L Tai, J H McReynolds, J A Goldstein, H P Eugster, C Sengstag, W L Alworth, J R Olson. Cytochrome P4501A1 mediates the metabolism of 2,3,7,8-tetrachlorodibenzofuran in the rat and human. Toxicology and applied pharmacology. 1993 Nov; 123(1):34-42. doi: 10.1006/taap.1993.1218. [PMID: 8236259]
  • H Liu, L Biegel, T R Narasimhan, C Rowlands, S Safe. Inhibition of insulin-like growth factor-I responses in MCF-7 cells by 2,3,7,8-tetrachlorodibenzo-p-dioxin and related compounds. Molecular and cellular endocrinology. 1992 Sep; 87(1-3):19-28. doi: 10.1016/0303-7207(92)90229-y. [PMID: 1332906]
  • J J Stegeman, R M Smolowitz, M E Hahn. Immunohistochemical localization of environmentally induced cytochrome P450IA1 in multiple organs of the marine teleost Stenotomus chrysops (Scup). Toxicology and applied pharmacology. 1991 Sep; 110(3):486-504. doi: 10.1016/0041-008x(91)90049-k. [PMID: 1949016]
  • R M Smolowitz, M E Hahn, J J Stegeman. Immunohistochemical localization of cytochrome P-450IA1 induced by 3,3',4,4'-tetrachlorobiphenyl and by 2,3,7,8-tetrachlorodibenzoafuran in liver and extrahepatic tissues of the teleost Stenotomus chrysops (scup). Drug metabolism and disposition: the biological fate of chemicals. 1991 Jan; 19(1):113-23. doi: . [PMID: 1708328]
  • A Berghard, K Gradin, R Toftgård. Serum and extracellular calcium modulate induction of cytochrome P-450IA1 in human keratinocytes. The Journal of biological chemistry. 1990 Dec; 265(34):21086-90. doi: 10.1016/s0021-9258(17)45330-0. [PMID: 1979076]
  • D W Brewster, Y B Banks, A M Clark, L S Birnbaum. Comparative dermal absorption of 2,3,7,8-tetrachlorodibenzo-p-dioxin and three polychlorinated dibenzofurans. Toxicology and applied pharmacology. 1989 Jan; 97(1):156-66. doi: 10.1016/0041-008x(89)90064-1. [PMID: 2916232]
  • D W Brewster, L S Birnbaum. Disposition of 1,2,3,7,8-pentachlorodibenzofuran in the rat. Toxicology and applied pharmacology. 1988 Sep; 95(3):490-8. doi: 10.1016/0041-008x(88)90367-5. [PMID: 3188012]
  • A Eschenroeder, R J Jaeger, J J Ospital, C P Doyle. Health risk analysis of human exposures to soil amended with sewage sludge contaminated with polychlorinated dibenzodioxins and dibenzofurans. Veterinary and human toxicology. 1986 Oct; 28(5):435-42. doi: ". [PMID: 3776090]
  • H Weber, L S Birnbaum. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) and 2,3,7,8-tetrachlorodibenzofuran (TCDF) in pregnant C57BL/6N mice: distribution to the embryo and excretion. Archives of toxicology. 1985 Aug; 57(3):159-62. doi: 10.1007/bf00290880. [PMID: 4062549]
  • H Weber, J C Lamb, M W Harris, J A Moore. Teratogenicity of 2.3.7.8-tetrachlorodibenzofuran (TCDF) in mice. Toxicology letters. 1984 Feb; 20(2):183-8. doi: 10.1016/0378-4274(84)90145-0. [PMID: 6695410]
  • E Hassoun, R d'Argy, L Dencker. Teratogenicity of 2,3,7,8-tetrachlorodibenzofuran in the mouse. Journal of toxicology and environmental health. 1984; 14(2-3):337-51. doi: 10.1080/15287398409530584. [PMID: 6502738]
  • F G King, R L Dedrick, J M Collins, H B Matthews, L S Birnbaum. Physiological model for the pharmacokinetics of 2,3,7,8-tetrachlorodibenzofuran in several species. Toxicology and applied pharmacology. 1983 Mar; 67(3):390-400. doi: 10.1016/0041-008x(83)90323-x. [PMID: 6405508]
  • L S Birnbaum, G M Decad, H B Matthews, E E McConnell. Fate of 2,3,7,8-tetrachlorodibenzofuran in the monkey. Toxicology and applied pharmacology. 1981 Feb; 57(2):189-96. doi: 10.1016/0041-008x(81)90279-9. [PMID: 7222035]