TDCPP (BioDeep_00000271454)

   

Industrial Pollutants


代谢物信息卡片


Tris(1,3-dichlorisopropyl)phosphate (TDCPP)

化学式: C9H15Cl6O4P (427.8839)
中文名称: 磷酸三(1,3-二氯-2-丙基)酯, 三（1,3-二氯-2-丙基）磷酸酯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C(CCl)OP(=O)(OC(CCl)CCl)OC(CCl)CCl)Cl
InChI: InChI=1S/C9H15Cl6O4P/c10-1-7(2-11)17-20(16,18-8(3-12)4-13)19-9(5-14)6-15/h7-9H,1-6H2

描述信息

CONFIDENCE standard compound; INTERNAL_ID 1036; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4548; ORIGINAL_PRECURSOR_SCAN_NO 4545
CONFIDENCE standard compound; INTERNAL_ID 1036; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4571; ORIGINAL_PRECURSOR_SCAN_NO 4569
CONFIDENCE standard compound; INTERNAL_ID 1036; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4552; ORIGINAL_PRECURSOR_SCAN_NO 4550
CONFIDENCE standard compound; INTERNAL_ID 1036; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4566; ORIGINAL_PRECURSOR_SCAN_NO 4563
CONFIDENCE standard compound; INTERNAL_ID 2469
CONFIDENCE standard compound; INTERNAL_ID 8809
CONFIDENCE standard compound; INTERNAL_ID 8194

同义名列表

6 个代谢物同义名

Tris(1,3-dichloro-2-propyl)phosphate; TDCPP; Tris(1,3-dichloro-2-propyl) phosphate; Tris(1,3-dichlorisopropyl)phosphate (TDCPP); TDCIPP; Tris(1,3-dichloro-2-propyl)phosphate



数据库引用编号

12 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

  • Xiaoshan Liu, Xiaoxun Lu, Jiabin Hong, Jing Zhang, Juntong Lin, Mengzhu Jiang, Qian Liu, Kyungho Choi, Jingjing Zhang. Effects of long-term exposure to TDCPP in zebrafish (Danio rerio) - Alternations of hormone balance and gene transcriptions along hypothalamus-pituitary axes. Animal models and experimental medicine. 2022 09; 5(3):239-247. doi: 10.1002/ame2.12215. [PMID: 35234363]
  • Yu Li, Kai Huang, Jieqiong Jiang, Yue Xiao, Lihui An, Shiyi Zhang, Qiyue Kang, Ruichao Chen, Yingting Jia, Xiaohua Zhang, Chunsheng Liu, Jianying Hu. Tris(1,3-dichloro-2-propyl)phosphate Induces Mass Mortality of Crucian Carp (Carassius carassius) Embryos in Taihu Lake. Environmental science & technology. 2021 12; 55(23):15980-15988. doi: 10.1021/acs.est.1c03746. [PMID: 34813318]
  • Chen Wang, Haibo Chen, Hui Li, Jun Yu, Xiaoli Wang, Yongdi Liu. Review of emerging contaminant tris(1,3-dichloro-2-propyl)phosphate: Environmental occurrence, exposure, and risks to organisms and human health. Environment international. 2020 10; 143(?):105946. doi: 10.1016/j.envint.2020.105946. [PMID: 32663715]
  • Qian Liu, Xuexi Tang, Xiaoyang Jian, Yingying Yang, Wenqian Ma, You Wang, Xinxin Zhang. Toxic effect and mechanism of tris (1,3-dichloro-2-propyl)phosphate (TDCPP) on the marine alga Phaeodactylum tricornutum. Chemosphere. 2020 Aug; 252(?):126467. doi: 10.1016/j.chemosphere.2020.126467. [PMID: 32222518]
  • 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]
  • Lei Wang, Xulei Huang, Anna Karen Carrasco Laserna, Sam Fong Yau Li. Metabolomics reveals that tris(1,3-dichloro-2-propyl)phosphate (TDCPP) causes disruption of membrane lipids in microalga Scenedesmus obliquus. The Science of the total environment. 2020 Mar; 708(?):134498. doi: 10.1016/j.scitotenv.2019.134498. [PMID: 31796289]
  • Simin Wang, Xiangang Hu, Xueyan Li. Sub-chronic exposure to Tris(1,3-dichloro-2-propyl) phosphate induces sex-dependent hepatotoxicity in rats. Environmental science and pollution research international. 2019 Nov; 26(32):33351-33362. doi: 10.1007/s11356-019-06383-5. [PMID: 31522405]
  • 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]
  • Petra Krystek, Henry Beeltje, Maarten Noteboom, Eric M van den Hoeven, Marc M G Houtzager. Analytical human biomonitoring method for the identification and quantification of the metabolite BDCPP originated from the organophosphate flame retardant TDCPP in urine. Journal of pharmaceutical and biomedical analysis. 2019 Jun; 170(?):169-175. doi: 10.1016/j.jpba.2019.03.036. [PMID: 30927662]
  • Xiaoshan Liu, Yi Cai, Yao Wang, Suhua Xu, Kyunghee Ji, Kyungho Choi. Effects of tris(1,3-dichloro-2-propyl) phosphate (TDCPP) and triphenyl phosphate (TPP) on sex-dependent alterations of thyroid hormones in adult zebrafish. Ecotoxicology and environmental safety. 2019 Apr; 170(?):25-32. doi: 10.1016/j.ecoenv.2018.11.058. [PMID: 30508752]
  • Chen Wang, Jing An, Yingchen Bai, Hui Li, Haibo Chen, Dong Ou, Yongdi Liu. Tris(1,3-dichloro-2-propyl) phosphate accelerated the aging process induced by the 4-hydroxynon-2-enal response to reactive oxidative species in Caenorhabditis elegans. Environmental pollution (Barking, Essex : 1987). 2019 Mar; 246(?):904-913. doi: 10.1016/j.envpol.2018.12.082. [PMID: 31159140]
  • 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]
  • Hiroyuki Kojima, Shinji Takeuchi, Nele Van den Eede, Adrian Covaci. Effects of primary metabolites of organophosphate flame retardants on transcriptional activity via human nuclear receptors. Toxicology letters. 2016 Mar; 245(?):31-9. doi: 10.1016/j.toxlet.2016.01.004. [PMID: 26778350]
  • Liping Feng, Fengxiu Ouyang, Liangpo Liu, Xu Wang, Xia Wang, Yi-Ju Li, Amy Murtha, Heqing Shen, Junfeng Zhang, Jun Jim Zhang. Levels of Urinary Metabolites of Organophosphate Flame Retardants, TDCIPP, and TPHP, in Pregnant Women in Shanghai. Journal of environmental and public health. 2016; 2016(?):9416054. doi: 10.1155/2016/9416054. [PMID: 28115951]
  • Kate Hoffman, Craig M Butt, Albert Chen, Alexander T Limkakeng, Heather M Stapleton. High Exposure to Organophosphate Flame Retardants in Infants: Associations with Baby Products. Environmental science & technology. 2015 Dec; 49(24):14554-9. doi: 10.1021/acs.est.5b03577. [PMID: 26551726]
  • Ya Zhu, Xufa Ma, Guanyong Su, Liqin Yu, Robert J Letcher, Jie Hou, Hongxia Yu, John P Giesy, Chunsheng Liu. Environmentally Relevant Concentrations of the Flame Retardant Tris(1,3-dichloro-2-propyl) Phosphate Inhibit Growth of Female Zebrafish and Decrease Fecundity. Environmental science & technology. 2015 Dec; 49(24):14579-87. doi: 10.1021/acs.est.5b03849. [PMID: 26512412]
  • Virginia C Moser, Pamela M Phillips, Joan M Hedge, Katherine L McDaniel. Neurotoxicological and thyroid evaluations of rats developmentally exposed to tris(1,3-dichloro-2-propyl)phosphate (TDCIPP) and tris(2-chloro-2-ethyl)phosphate (TCEP). Neurotoxicology and teratology. 2015 Nov; 52(Pt B):236-47. doi: 10.1016/j.ntt.2015.08.004. [PMID: 26300399]
  • Tao Xu, Qiangwei Wang, Qipeng Shi, Qi Fang, Yongyong Guo, Bingsheng Zhou. Bioconcentration, metabolism and alterations of thyroid hormones of Tris(1,3-dichloro-2-propyl) phosphate (TDCPP) in Zebrafish. Environmental toxicology and pharmacology. 2015 Sep; 40(2):581-6. doi: 10.1016/j.etap.2015.08.020. [PMID: 26356387]
  • Qiangwei Wang, Nelson Lok-Shun Lai, Xianfeng Wang, Yongyong Guo, Paul Kwan-Sing Lam, James Chung-Wah Lam, Bingsheng Zhou. Bioconcentration and transfer of the organophorous flame retardant 1,3-dichloro-2-propyl phosphate causes thyroid endocrine disruption and developmental neurotoxicity in zebrafish larvae. Environmental science & technology. 2015 Apr; 49(8):5123-32. doi: 10.1021/acs.est.5b00558. [PMID: 25826601]
  • Qiangwei Wang, James C W Lam, Jian Han, Xianfeng Wang, Yongyong Guo, Paul K S Lam, Bingsheng Zhou. Developmental exposure to the organophosphorus flame retardant tris(1,3-dichloro-2-propyl) phosphate: estrogenic activity, endocrine disruption and reproductive effects on zebrafish. Aquatic toxicology (Amsterdam, Netherlands). 2015 Mar; 160(?):163-71. doi: 10.1016/j.aquatox.2015.01.014. [PMID: 25637911]
  • Kate Hoffman, Stavros Garantziotis, Linda S Birnbaum, Heather M Stapleton. Monitoring indoor exposure to organophosphate flame retardants: hand wipes and house dust. Environmental health perspectives. 2015 Feb; 123(2):160-5. doi: 10.1289/ehp.1408669. [PMID: 25343780]
  • Ellen L Berg, Mark A Polokoff, Alison O'Mahony, Dat Nguyen, Xitong Li. Elucidating mechanisms of toxicity using phenotypic data from primary human cell systems--a chemical biology approach for thrombosis-related side effects. International journal of molecular sciences. 2015 Jan; 16(1):1008-29. doi: 10.3390/ijms16011008. [PMID: 25569083]
  • Amani Farhat, Doug Crump, Emily Porter, Suzanne Chiu, Robert J Letcher, Guanyong Su, Sean W Kennedy. Time-dependent effects of the flame retardant tris(1,3-dichloro-2-propyl) phosphate (TDCPP) on mRNA expression, in vitro and in ovo, reveal optimal sampling times for rapidly metabolized compounds. Environmental toxicology and chemistry. 2014 Dec; 33(12):2842-9. doi: 10.1002/etc.2755. [PMID: 25242413]
  • Erika D Schreder, Mark J La Guardia. Flame retardant transfers from U.S. households (dust and laundry wastewater) to the aquatic environment. Environmental science & technology. 2014 Oct; 48(19):11575-83. doi: 10.1021/es502227h. [PMID: 25288150]
  • Zhihua Han, Qiangwei Wang, Jie Fu, Hongshan Chen, Ye Zhao, Bingsheng Zhou, Zhiyuan Gong, Si Wei, Jun Li, Hongling Liu, Xiaowei Zhang, Chunsheng Liu, Hongxia Yu. Multiple bio-analytical methods to reveal possible molecular mechanisms of developmental toxicity in zebrafish embryos/larvae exposed to tris(2-butoxyethyl) phosphate. Aquatic toxicology (Amsterdam, Netherlands). 2014 May; 150(?):175-81. doi: 10.1016/j.aquatox.2014.03.013. [PMID: 24685621]
  • 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]
  • Amani Farhat, Julie K Buick, Andrew Williams, Carole L Yauk, Jason M O'Brien, Doug Crump, Kim L Williams, Suzanne Chiu, Sean W Kennedy. Tris(1,3-dichloro-2-propyl) phosphate perturbs the expression of genes involved in immune response and lipid and steroid metabolism in chicken embryos. Toxicology and applied pharmacology. 2014 Mar; 275(2):104-12. doi: 10.1016/j.taap.2013.12.020. [PMID: 24407104]
  • Amani Farhat, Doug Crump, Suzanne Chiu, Kim L Williams, Robert J Letcher, Lewis T Gauthier, Sean W Kennedy. In Ovo effects of two organophosphate flame retardants--TCPP and TDCPP--on pipping success, development, mRNA expression, and thyroid hormone levels in chicken embryos. Toxicological sciences : an official journal of the Society of Toxicology. 2013 Jul; 134(1):92-102. doi: 10.1093/toxsci/kft100. [PMID: 23629516]
  • Xiaoshan Liu, Kyunghee Ji, Areum Jo, Hyo-Bang Moon, Kyungho Choi. Effects of TDCPP or TPP on gene transcriptions and hormones of HPG axis, and their consequences on reproduction in adult zebrafish (Danio rerio). Aquatic toxicology (Amsterdam, Netherlands). 2013 Jun; 134-135(?):104-11. doi: 10.1016/j.aquatox.2013.03.013. [PMID: 23603146]
  • John D Meeker, Ellen M Cooper, Heather M Stapleton, Russ Hauser. Urinary metabolites of organophosphate flame retardants: temporal variability and correlations with house dust concentrations. Environmental health perspectives. 2013 May; 121(5):580-5. doi: 10.1289/ehp.1205907. [PMID: 23461877]
  • 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]
  • Doug Crump, Suzanne Chiu, Sean W Kennedy. Effects of tris(1,3-dichloro-2-propyl) phosphate and tris(1-chloropropyl) phosphate on cytotoxicity and mRNA expression in primary cultures of avian hepatocytes and neuronal cells. Toxicological sciences : an official journal of the Society of Toxicology. 2012 Mar; 126(1):140-8. doi: 10.1093/toxsci/kfs015. [PMID: 22268003]
  • E Kamata, K Naito, Y Nakaji, Y Ogawa, S Suzuki, T Kaneko, K Takada, Y Kurokawa, M Tobe. [Acute and subacute toxicity studies of tris (1,3-dichloro-2-propyl) phosphate on mice]. Eisei Shikenjo hokoku. Bulletin of National Institute of Hygienic Sciences. 1989; ?(107):36-43. doi: NULL. [PMID: 2636931]
  • U Sellström, B Jansson. Mass spectrometric determination of tris(1,3-dichloro-2-propyl)-phosphate (TDCP) using NCI-technique. International journal of environmental analytical chemistry. 1987; 29(4):277-87. doi: 10.1080/03067318708075447. [PMID: 3596894]
  • E J Søderlund, E Dybing, J A Holme, J K Hongslo, E Rivedal, T Sanner, S D Nelson. Comparative genotoxicity and nephrotoxicity studies of the two halogenated flame retardants tris(1,3-dichloro-2-propyl)phosphate and tris(2,3-dibromopropyl)phosphate. Acta pharmacologica et toxicologica. 1985 Jan; 56(1):20-9. doi: 10.1111/j.1600-0773.1985.tb01248.x. [PMID: 3883695]
  • N M Morales, H B Matthews. In vivo binding of the flame retardants tris(2,3-dibromopropyl) phosphate and tris(1,3-dichloro-2-propyl) phosphate to macromolecules of mouse liver, kidney and muscle. Bulletin of environmental contamination and toxicology. 1980 Jul; 25(1):34-8. doi: 10.1007/bf01985482. [PMID: 6161654]
  • R K Lynn, K Wong, R G Dickinson, N Gerber, J M Kennish. Diester metabolites of the flame retardant chemicals, tris(1,3-dichloro-2-propyl)phosphate and tris(2,3-dibromopropyl) phosphate in the rat: identification and quantification. Research communications in chemical pathology and pharmacology. 1980 May; 28(2):351-60. doi: NULL. [PMID: 7394328]
  • D Brusick, D Matheson, D R Jagannath, S Goode, H Lebowitz, M Reed, G Roy, S Benson. A comparison of the genotoxic properties of tris(2,3-dibromopropyl)phosphate and tris(1,3-dichloro-2-propyl)phosphate in a battery of short-term bioassays. Journal of environmental pathology and toxicology. 1979 Dec; 3(1-2):207-26. doi: NULL. [PMID: 121137]