Benzo[a]pyrene-7,8-diol (BioDeep_00000010187)

 

Secondary id: BioDeep_00001875413

human metabolite


代谢物信息卡片


pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol

化学式: C20H14O2 (286.0993744)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 7.71%

分子结构信息

SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C=CC(C5O)O)C=C2
InChI: InChI=1S/C20H14O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10,17,20-22H



数据库引用编号

10 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

  • Fabian C Fischer, Cedric Abele, Luise Henneberger, Nils Klüver, Maria König, Marie Mühlenbrink, Rita Schlichting, Beate I Escher. Cellular Metabolism in High-Throughput In Vitro Reporter Gene Assays and Implications for the Quantitative In Vitro-In Vivo Extrapolation. Chemical research in toxicology. 2020 07; 33(7):1770-1779. doi: 10.1021/acs.chemrestox.0c00037. [PMID: 32227843]
  • Guoxiang Huang, Huan Guo, Tangchun Wu. Genetic variations of CYP2B6 gene were associated with plasma BPDE-Alb adducts and DNA damage levels in coke oven workers. Toxicology letters. 2012 Jun; 211(3):232-8. doi: 10.1016/j.toxlet.2012.04.004. [PMID: 22521834]
  • Piya Temviriyanukul, Matty Meijers, Sandrine van Hees-Stuivenberg, Jan J W A Boei, Frédéric Delbos, Haruo Ohmori, Niels de Wind, Jacob G Jansen. Different sets of translesion synthesis DNA polymerases protect from genome instability induced by distinct food-derived genotoxins. Toxicological sciences : an official journal of the Society of Toxicology. 2012 May; 127(1):130-8. doi: 10.1093/toxsci/kfs074. [PMID: 22331492]
  • Ryan T Bushey, Gang Chen, Andrea S Blevins-Primeau, Jacek Krzeminski, Shantu Amin, Philip Lazarus. Characterization of UDP-glucuronosyltransferase 2A1 (UGT2A1) variants and their potential role in tobacco carcinogenesis. Pharmacogenetics and genomics. 2011 Feb; 21(2):55-65. doi: 10.1097/fpc.0b013e328341db05. [PMID: 21164388]
  • Caroline Marie-Desvergne, Anne Maître, Michèle Bouchard, Jean-Luc Ravanat, Claude Viau. Evaluation of DNA adducts, DNA and RNA oxidative lesions, and 3-hydroxybenzo(a)pyrene as biomarkers of DNA damage in lung following intravenous injection of the parent compound in rats. Chemical research in toxicology. 2010 Jul; 23(7):1207-14. doi: 10.1021/tx100081p. [PMID: 20593881]
  • Haitian Lu, Robert B Crawford, Colin M North, Barbara L F Kaplan, Norbert E Kaminski. Establishment of an immunoglobulin m antibody-forming cell response model for characterizing immunotoxicity in primary human B cells. Toxicological sciences : an official journal of the Society of Toxicology. 2009 Dec; 112(2):363-73. doi: 10.1093/toxsci/kfp224. [PMID: 19767444]
  • Peter H Bui, Erin L Hsu, Oliver Hankinson. Fatty acid hydroperoxides support cytochrome P450 2S1-mediated bioactivation of benzo[a]pyrene-7,8-dihydrodiol. Molecular pharmacology. 2009 Nov; 76(5):1044-52. doi: 10.1124/mol.109.057760. [PMID: 19713357]
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  • Yaqin Pang, Wenxue Li, Rulin Ma, Weidong Ji, Qing Wang, Daochuan Li, Yongmei Xiao, Qing Wei, Yandong Lai, Ping Yang, Liping Chen, Shifu Tang, Yuchun Lin, Zhixiong Zhuang, Yuxin Zheng, Wen Chen. Development of human cell models for assessing the carcinogenic potential of chemicals. Toxicology and applied pharmacology. 2008 Nov; 232(3):478-86. doi: 10.1016/j.taap.2008.08.009. [PMID: 18778725]
  • Yimin Zhu, Yohei Horikawa, Hushan Yang, Christopher G Wood, Tomonori Habuchi, Xifeng Wu. BPDE induced lymphocytic chromosome 3p deletions may predict renal cell carcinoma risk. The Journal of urology. 2008 Jun; 179(6):2416-21. doi: 10.1016/j.juro.2008.01.092. [PMID: 18433782]
  • Jingxia Li, Dongyun Zhang, Gary D Stoner, Chuanshu Huang. Differential effects of black raspberry and strawberry extracts on BaPDE-induced activation of transcription factors and their target genes. Molecular carcinogenesis. 2008 Apr; 47(4):286-94. doi: 10.1002/mc.20377. [PMID: 18085529]
  • Haruhiko Yagi, Donald M Jerina. Fluorinated alcohol mediated displacement of the C10 acetoxy group of benzo[a]pyrene-7,8,9,10-tetrahydrotetraol tetraacetates: a new route to diol epoxide-deoxyguanosine adducts. The Journal of organic chemistry. 2007 Dec; 72(26):9983-90. doi: 10.1021/jo701705c. [PMID: 18047370]
  • Hong Wang, Weihong Chen, Hongyan Zheng, Liang Guo, Huashan Liang, Xiaobo Yang, Yun Bai, Jianya Sun, Yougong Su, Yongwen Chen, Jing Yuan, Yongyi Bi, Qingyi Wei, Tangchun Wu. Association between plasma BPDE-Alb adduct concentrations and DNA damage of peripheral blood lymphocytes among coke oven workers. Occupational and environmental medicine. 2007 Nov; 64(11):753-8. doi: 10.1136/oem.2006.030445. [PMID: 17449561]
  • Lonneke C Wilms, Agnes W Boots, Vincent C J de Boer, Lou M Maas, Daniëlle M F A Pachen, Ralph W H Gottschalk, Hans B Ketelslegers, Roger W L Godschalk, Guido R M M Haenen, Frederik J van Schooten, Jos C S Kleinjans. Impact of multiple genetic polymorphisms on effects of a 4-week blueberry juice intervention on ex vivo induced lymphocytic DNA damage in human volunteers. Carcinogenesis. 2007 Aug; 28(8):1800-6. doi: 10.1093/carcin/bgm145. [PMID: 17602170]
  • Hong Wang, Xiao-Bo Yang, Ai-Lin Liu, Hong-Yan Zhen, Liang Guo, Hua-Shan Liang, Yong-Yi Bi, Yun Bai, Yong-Wen Chen, Tang-Chun Wu. Significant positive correlation of plasma BPDE-albumin adducts to urinary 1-hydroxypyrene in coke oven workers. Biomedical and environmental sciences : BES. 2007 Jun; 20(3):179-83. doi: . [PMID: 17672206]
  • Bettina Ebert, Albrecht Seidel, Alfonso Lampen. Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate. Toxicological sciences : an official journal of the Society of Toxicology. 2007 Apr; 96(2):227-36. doi: 10.1093/toxsci/kfl147. [PMID: 17077187]
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  • Stephen S Hecht, Chuanshu Huang, Gary D Stoner, Jingxia Li, Patrick M J Kenney, Shana J Sturla, Steven G Carmella. Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit anti-benzo[a]pyrene-7,8-diol-9,10-epoxide induced NFkappaB and AP-1 activity. Carcinogenesis. 2006 Aug; 27(8):1617-26. doi: 10.1093/carcin/bgi366. [PMID: 16522666]
  • Chuanshu Huang, Jingxia Li, Lun Song, Dongyun Zhang, Qiangsong Tong, Min Ding, Linda Bowman, Robeena Aziz, Gary D Stoner. Black raspberry extracts inhibit benzo(a)pyrene diol-epoxide-induced activator protein 1 activation and VEGF transcription by targeting the phosphotidylinositol 3-kinase/Akt pathway. Cancer research. 2006 Jan; 66(1):581-7. doi: 10.1158/0008-5472.can-05-1951. [PMID: 16397275]
  • Hans Steinkellner, Christine Hoelzl, Maria Uhl, Christophe Cavin, Gerald Haidinger, Andrea Gsur, Rainer Schmid, Michael Kundi, Julia Bichler, Siegfried Knasmüller. Coffee consumption induces GSTP in plasma and protects lymphocytes against (+/-)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide induced DNA-damage: results of controlled human intervention trials. Mutation research. 2005 Dec; 591(1-2):264-75. doi: 10.1016/j.mrfmmm.2005.04.016. [PMID: 16099480]
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  • Michael J Kelley, Elizabeth M Glaser, James E Herndon, Frank Becker, Rajesh Bhagat, Yu-Jing Zhang, Regina M Santella, Steven G Carmella, Stephen S Hecht, Lilia Gallot, Lawrence Schilder, James A Crowell, Marjorie Perloff, Rodney J Folz, Raymond C Bergan. Safety and efficacy of weekly oral oltipraz in chronic smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2005 Apr; 14(4):892-9. doi: 10.1158/1055-9965.epi-04-0585. [PMID: 15824161]
  • Wei Yang. Portraits of a Y-family DNA polymerase. FEBS letters. 2005 Feb; 579(4):868-72. doi: 10.1016/j.febslet.2004.11.047. [PMID: 15680965]
  • Huan Dong, Radha Rani Bonala, Naomi Suzuki, Francis Johnson, Arthur P Grollman, Shinya Shibutani. Mutagenic potential of benzo[a]pyrene-derived DNA adducts positioned in codon 273 of the human P53 gene. Biochemistry. 2004 Dec; 43(50):15922-8. doi: 10.1021/bi0482194. [PMID: 15595848]
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  • Roger Godschalk, Daniëlle Curfs, Helmut Bartsch, Frederik-Jan Van Schooten, Jagadeesan Nair. Benzo[a]pyrene enhances lipid peroxidation induced DNA damage in aorta of apolipoprotein E knockout mice. Free radical research. 2003 Dec; 37(12):1299-305. doi: 10.1080/10715760310001621333. [PMID: 14753754]
  • Stephen S Hecht, Menglan Chen, Haruhiko Yagi, Donald M Jerina, Steven G Carmella. r-1,t-2,3,c-4-Tetrahydroxy-1,2,3,4-tetrahydrophenanthrene in human urine: a potential biomarker for assessing polycyclic aromatic hydrocarbon metabolic activation. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2003 Dec; 12(12):1501-8. doi: . [PMID: 14693744]
  • Dieter Schwarz, Pyotr Kisselev, Ivar Roots. St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1. Cancer research. 2003 Nov; 63(22):8062-8. doi: . [PMID: 14633740]
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  • Chuanshu Huang, Yi Huang, Jingxia Li, Wenwei Hu, Robeena Aziz, Moon-shong Tang, Nanjun Sun, John Cassady, Gary D Stoner. Inhibition of benzo(a)pyrene diol-epoxide-induced transactivation of activated protein 1 and nuclear factor kappaB by black raspberry extracts. Cancer research. 2002 Dec; 62(23):6857-63. doi: . [PMID: 12460899]
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