Tricresylphosphate (BioDeep_00000402598)

   


代谢物信息卡片


Tris(4-methylphenyl) phosphate

化学式: C21H21O4P (368.11773960000005)
中文名称: 三对甲苯基磷酸酯, 邻磷酸三甲酚酯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C(OP(=O)(OC2=C(C)C=CC=C2)OC2=C(C)C=CC=C2)C=CC=C1
InChI: InChI=1S/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3

描述信息

CONFIDENCE standard compound; INTERNAL_ID 2476
CONFIDENCE standard compound; INTERNAL_ID 8832

同义名列表

5 个代谢物同义名

Tris(4-methylphenyl) phosphate; TRICRESYL PHOSPHATE; Tricresylphosphate; Tris(2-methylphenyl) phosphate; TRI-O-CRESYL PHOSPHATE



数据库引用编号

14 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)

0 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

  • Jing Li, Yi-Jun Wu. Tri-ortho-cresyl phosphate induces hepatic steatosis by mTOR activation and ER stress induction. Ecotoxicology and environmental safety. 2024 Feb; 271(?):116010. doi: 10.1016/j.ecoenv.2024.116010. [PMID: 38280340]
  • Dandan Xiang, Qiangwei Wang. PXR-mediated organophorous flame retardant tricresyl phosphate effects on lipid homeostasis. Chemosphere. 2021 Dec; 284(?):131250. doi: 10.1016/j.chemosphere.2021.131250. [PMID: 34225124]
  • Helena T Hogberg, Rita de Cássia da Silveira E Sá, Andre Kleensang, Mounir Bouhifd, Ozge Cemiloglu Ulker, Lena Smirnova, Mamta Behl, Alexandra Maertens, Liang Zhao, Thomas Hartung. Organophosphorus flame retardants are developmental neurotoxicants in a rat primary brainsphere in vitro model. Archives of toxicology. 2021 01; 95(1):207-228. doi: 10.1007/s00204-020-02903-2. [PMID: 33078273]
  • Samantha Adams, Kimberly Wiersielis, Ali Yasrebi, Kristie Conde, Laura Armstrong, Grace L Guo, Troy A Roepke. Sex- and age-dependent effects of maternal organophosphate flame-retardant exposure on neonatal hypothalamic and hepatic gene expression. Reproductive toxicology (Elmsford, N.Y.). 2020 06; 94(?):65-74. doi: 10.1016/j.reprotox.2020.04.001. [PMID: 32360330]
  • Zhengliang Hao, Zhijie Zhang, Dezhao Lu, Bin Ding, Lin Shu, Quan Zhang, Cui Wang. Organophosphorus Flame Retardants Impair Intracellular Lipid Metabolic Function in Human Hepatocellular Cells. Chemical research in toxicology. 2019 06; 32(6):1250-1258. doi: 10.1021/acs.chemrestox.9b00058. [PMID: 30966736]
  • Junqi Li, Zheng Dong, Ying Wang, Junsong Bao, Yijun Yan, Jun Jin. Different organophosphate flame retardant and metabolite concentrations in urine from male and female university students in Beijing and an assessment of exposure via indoor dust. Environmental toxicology and chemistry. 2019 04; 38(4):760-768. doi: 10.1002/etc.4365. [PMID: 30657202]
  • Fanrong Zhao, Qiyue Kang, Xiaohua Zhang, Jiaying Liu, Jianying Hu. Urinary biomarkers for assessment of human exposure to monomeric aryl phosphate flame retardants. Environment international. 2019 03; 124(?):259-264. doi: 10.1016/j.envint.2019.01.022. [PMID: 30660026]
  • Valentina Pomatto, Erika Cottone, Paolo Cocci, Matteo Mozzicafreddo, Gilberto Mosconi, Erik Russel Nelson, Francesco Alessandro Palermo, Patrizia Bovolin. Plasticizers used in food-contact materials affect adipogenesis in 3T3-L1 cells. The Journal of steroid biochemistry and molecular biology. 2018 04; 178(?):322-332. doi: 10.1016/j.jsbmb.2018.01.014. [PMID: 29410257]
  • Elizabeth A Krumm, Vipa J Patel, Taylor S Tillery, Ali Yasrebi, Jianliang Shen, Grace L Guo, Stephanie M Marco, Brian T Buckley, Troy A Roepke. Organophosphate Flame-Retardants Alter Adult Mouse Homeostasis and Gene Expression in a Sex-Dependent Manner Potentially Through Interactions With ERα. Toxicological sciences : an official journal of the Society of Toxicology. 2018 03; 162(1):212-224. doi: 10.1093/toxsci/kfx238. [PMID: 29112739]
  • Shohei Yamashita, Shingo Oda, Hideko Endo, Koichi Tsuneyama, Tsuyoshi Yokoi. Neutrophil depletion protects against zomepirac-induced acute kidney injury in mice. Chemico-biological interactions. 2018 Jan; 279(?):102-110. doi: 10.1016/j.cbi.2017.11.011. [PMID: 29154782]
  • L L Xu, C Y Long, J L Wang, M Yu, J X Chen. Involvement of oxidative stress in tri-ortho-cresyl phosphate-induced liver injury in male mice. Human & experimental toxicology. 2016 Oct; 35(10):1093-101. doi: 10.1177/0960327115621363. [PMID: 26757727]
  • Atsushi Iwamura, Katsuhito Watanabe, Sho Akai, Tsubasa Nishinosono, Koichi Tsuneyama, Shingo Oda, Toshiyuki Kume, Tsuyoshi Yokoi. Zomepirac Acyl Glucuronide Is Responsible for Zomepirac-Induced Acute Kidney Injury in Mice. Drug metabolism and disposition: the biological fate of chemicals. 2016 07; 44(7):888-96. doi: 10.1124/dmd.116.069575. [PMID: 27112166]
  • Francesco Alessandro Palermo, Paolo Cocci, Matteo Mozzicafreddo, Augustine Arukwe, Mauro Angeletti, Graziano Aretusi, Gilberto Mosconi. Tri-m-cresyl phosphate and PPAR/LXR interactions in seabream hepatocytes: revealed by computational modeling (docking) and transcriptional regulation of signaling pathways. Toxicology research. 2016 Mar; 5(2):471-481. doi: 10.1039/c5tx00314h. [PMID: 30090361]
  • Darryl Johnson, Melissa D Carter, Brian S Crow, Samantha L Isenberg, Leigh Ann Graham, H Akin Erol, Caroline M Watson, Brooke G Pantazides, Marcel J van der Schans, Jan P Langenberg, Daan Noort, Thomas A Blake, Jerry D Thomas, Rudolph C Johnson. Quantitation of ortho-cresyl phosphate adducts to butyrylcholinesterase in human serum by immunomagnetic-UHPLC-MS/MS. Journal of mass spectrometry : JMS. 2015 Apr; 50(4):683-92. doi: 10.1002/jms.3576. [PMID: 26149113]
  • Judith Anderson. Comment on Schindler, BK; Weiss, T; Schütze, A; et al. 'Occupational exposure of air crews to tricresyl phosphate isomers and organophosphate flame retardants after fume events,' Arch Toxicol (2013) 87:645-648. Archives of toxicology. 2015 Feb; 89(2):259-61. doi: 10.1007/s00204-014-1441-1. [PMID: 25537188]
  • Tobias Weiss, Birgit Karin Schindler, André Schütze, Stephan Koslitz, Horst Christoph Broding, Jürgen Bünger, Thomas Brüning. Reply to the letter of Anderson J entitled 'Comment on Schindler, BK; Weiss, T; Schütze, A; et al. Occupational exposure of air crews to tricresyl phosphate isomers and organophosphate flame retardants after fume events, Arch Toxicol (2013) 87:645-648'. Archives of toxicology. 2015 Feb; 89(2):263-4. doi: 10.1007/s00204-015-1449-1. [PMID: 25586888]
  • Lawrence M Schopfer, Patrick Masson, Patricia Lamourette, Stéphanie Simon, Oksana Lockridge. Detection of cresyl phosphate-modified butyrylcholinesterase in human plasma for chemical exposure associated with aerotoxic syndrome. Analytical biochemistry. 2014 Sep; 461(?):17-26. doi: 10.1016/j.ab.2014.05.021. [PMID: 24892986]
  • Ozden Tacal, Lawrence M Schopfer. Healthy F-16 pilots show no evidence of exposure to tri-ortho-cresyl phosphate through the on-board oxygen generating system. Chemico-biological interactions. 2014 May; 215(?):69-74. doi: 10.1016/j.cbi.2014.03.004. [PMID: 24661946]
  • Patrick J Morris, Daniel Medina-Cleghorn, Ann Heslin, Sarah M King, Joseph Orr, Melinda M Mulvihill, Ronald M Krauss, Daniel K Nomura. Organophosphorus flame retardants inhibit specific liver carboxylesterases and cause serum hypertriglyceridemia. ACS chemical biology. 2014 May; 9(5):1097-103. doi: 10.1021/cb500014r. [PMID: 24597639]
  • Emily Porter, Doug Crump, Caroline Egloff, Suzanne Chiu, Sean W Kennedy. Use of an avian hepatocyte assay and the avian Toxchip Polymerse chain reaction array for testing prioritization of 16 organic flame retardants. Environmental toxicology and chemistry. 2014 Mar; 33(3):573-82. doi: 10.1002/etc.2469. [PMID: 24273086]
  • Birgit Karin Schindler, Tobias Weiss, Andre Schütze, Stephan Koslitz, Horst Christoph Broding, Jürgen Bünger, Thomas Brüning. Occupational exposure of air crews to tricresyl phosphate isomers and organophosphate flame retardants after fume events. Archives of toxicology. 2013 Apr; 87(4):645-8. doi: 10.1007/s00204-012-0978-0. [PMID: 23179756]
  • Yuki Kobayashi, Tatsuki Fukami, Ryota Higuchi, Miki Nakajima, Tsuyoshi Yokoi. Metabolic activation by human arylacetamide deacetylase, CYP2E1, and CYP1A2 causes phenacetin-induced methemoglobinemia. Biochemical pharmacology. 2012 Nov; 84(9):1196-206. doi: 10.1016/j.bcp.2012.08.015. [PMID: 22940574]
  • Mariya S Liyasova, Lawrence M Schopfer, Oksana Lockridge. Cresyl saligenin phosphate, an organophosphorus toxicant, makes covalent adducts with histidine, lysine, and tyrosine residues of human serum albumin. Chemical research in toxicology. 2012 Aug; 25(8):1752-61. doi: 10.1021/tx300215g. [PMID: 22793878]
  • Ike van der Veen, Jacob de Boer. Phosphorus flame retardants: properties, production, environmental occurrence, toxicity and analysis. Chemosphere. 2012 Aug; 88(10):1119-53. doi: 10.1016/j.chemosphere.2012.03.067. [PMID: 22537891]
  • Xiaoshan Liu, Kyunghee Ji, Kyungho Choi. Endocrine disruption potentials of organophosphate flame retardants and related mechanisms in H295R and MVLN cell lines and in zebrafish. Aquatic toxicology (Amsterdam, Netherlands). 2012 Jun; 114-115(?):173-81. doi: 10.1016/j.aquatox.2012.02.019. [PMID: 22446829]
  • Mariya Liyasova, Bin Li, Lawrence M Schopfer, Florian Nachon, Patrick Masson, Clement E Furlong, Oksana Lockridge. Exposure to tri-o-cresyl phosphate detected in jet airplane passengers. Toxicology and applied pharmacology. 2011 Nov; 256(3):337-47. doi: 10.1016/j.taap.2011.06.016. [PMID: 21723309]
  • Ellen G Duysen, Oksana Lockridge. Induction of plasma acetylcholinesterase activity in mice challenged with organophosphorus poisons. Toxicology and applied pharmacology. 2011 Sep; 255(2):214-20. doi: 10.1016/j.taap.2011.06.021. [PMID: 21767560]
  • Kuntal Bhattacharyya, Sibaji Phaujdar, Rathindranath Sarkar, Omar S Mullick. Serum creatine phosphokinase: a probable marker of severity in organophosphorus poisoning. Toxicology international. 2011 Jul; 18(2):117-23. doi: 10.4103/0971-6580.84263. [PMID: 21976816]
  • Eman Y Z Frag, Gehad G Mohamed, Mohamed M Khalil, Mohammad M A Hwehy. Potentiometric determination of ketotifen fumarate in pharmaceutical preparations and urine using carbon paste and PVC membrane selective electrodes. International journal of analytical chemistry. 2011; 2011(?):604741. doi: 10.1155/2011/604741. [PMID: 22013443]
  • Lawrence M Schopfer, Clement E Furlong, Oksana Lockridge. Development of diagnostics in the search for an explanation of aerotoxic syndrome. Analytical biochemistry. 2010 Sep; 404(1):64-74. doi: 10.1016/j.ab.2010.04.032. [PMID: 20447373]
  • A M Kammon, R S Brar, S Sodhi, H S Banga, H S Sandhu. Neuropathological studies of chickens following exposure to chlorpyrifos. Toxicology international. 2010 Jul; 17(2):78-81. doi: 10.4103/0971-6580.72675. [PMID: 21170250]
  • Horst Gross. ['Aerotoxic syndrome:' danger caused by hydraulic oil in aircraft?]. Deutsche medizinische Wochenschrift (1946). 2010 May; 135(19):p18. doi: 10.1055/s-0030-1247682. [PMID: 20461667]
  • Wei-Yuan Hou, Ding-Xin Long, Hui-Ping Wang, Qi Wang, Yi-Jun Wu. The homeostasis of phosphatidylcholine and lysophosphatidylcholine was not disrupted during tri-o-cresyl phosphate-induced delayed neurotoxicity in hens. Toxicology. 2008 Oct; 252(1-3):56-63. doi: 10.1016/j.tox.2008.07.061. [PMID: 18755237]
  • Hassan A N El-Fawal, Wilfred C McCain. Antibodies to neural proteins in organophosphorus-induced delayed neuropathy (OPIDN) and its amelioration. Neurotoxicology and teratology. 2008 May; 30(3):161-6. doi: 10.1016/j.ntt.2008.01.005. [PMID: 18353611]
  • G A Muzardo, R G P Machado, G Honorato de Oliveira. Effects of calcium gluconate and PMSF in the treatment of acute intoxication of chicken by TOCP. Human & experimental toxicology. 2008 Mar; 27(3):247-52. doi: 10.1177/0960327108090273. [PMID: 18650257]
  • Jun Tang, Teruaki Akao, Norio Nakamura, Zheng-Tao Wang, Kiyoshi Takagawa, Masakiyo Sasahara, Masao Hattori. In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors. Drug metabolism and disposition: the biological fate of chemicals. 2007 Oct; 35(10):1832-9. doi: 10.1124/dmd.107.016311. [PMID: 17639025]
  • Li-Ping Zhang, Qing-Shan Wang, Xin Guo, Ying-Jian Zhu, Gui-Zhen Zhou, Ke-Qin Xie. Time-dependent changes of lipid peroxidation and antioxidative status in nerve tissues of hens treated with tri-ortho-cresyl phosphate (TOCP). Toxicology. 2007 Sep; 239(1-2):45-52. doi: 10.1016/j.tox.2007.06.091. [PMID: 17662514]
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  • Kelly A Mericle, Bhupendra S Kaphalia, G A S Ansari. Differential inhibition of hepatic, pancreatic, and plasma fatty acid ethyl ester synthase by tri-o-tolylphosphate in rats. Toxicology and applied pharmacology. 2002 Mar; 179(2):119-25. doi: 10.1006/taap.2001.9361. [PMID: 11884245]
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  • Y J Wu, X F Leng. Effects of tri-o-cresyl phosphate on serum estrogen and progesterone concentration and ATPase activity in the shell gland of adult hens. Chemosphere. 2000 Jul; 41(1-2):183-6. doi: 10.1016/s0045-6535(99)00409-9. [PMID: 10819199]
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