4-Aminobiphenyl (BioDeep_00000001874)

   

human metabolite Endogenous Volatile Flavor Compounds


代谢物信息卡片


[1,1-Biphenyl]-4-ylamine (acd/name 4.0)

化学式: C12H11N (169.0891446)
中文名称: 4-氨基联苯
谱图信息: 最多检出来源 Mentha canadensis(plant) 85.71%

分子结构信息

SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)N
InChI: InChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2

描述信息

4-Aminobiphenyl is an amine derivative of biphenyl. It is used to manufacture azo dyes. It is a known human carcinogen and so it has been largely replaced by less toxic compounds. It is similar to benzidine. [HMDB]
4-Aminobiphenyl is an amine derivative of biphenyl. It is used to manufacture azo dyes. It is a known human carcinogen and so it has been largely replaced by less toxic compounds. It is similar to benzidine.
D009676 - Noxae > D002273 - Carcinogens

同义名列表

31 个代谢物同义名

[1,1-Biphenyl]-4-ylamine (acd/name 4.0); [1,1-Biphenyl]-4-amine (acd/name 4.0); 4-Biphenylamine hydrochloride; {[1,1-biphenyl]-4-amine}; (4-Phenyl-phenyl)-amine; 4-Biphenylnitrenium ion; (1,1-Biphenyl)-4-amine; [1,1-Biphenyl]-4-amine; 4-Amino-1,1-biphenyl; Biphenyl-4-ylamine; Paraaminodiphenyl; 4-Biphenylylamine; Biphenyl-4-amine; p-Aminodiphenyl; 4-Biphenylamine; P-Aminobiphenyl; 4-Aminobiphenyl; 4-Aminodiphenyl; p-Biphenylamine; p-Phenylaniline; 4-Phenylaniline; 4-Aminobifenyl; 4-Aminodifenil; Biphenylamine; Aminobiphenyl; 4-Bifenylamin; p-Xenylamine; Xenylamine; Xenylamin; 4-Aminobiphenyl; 4-Aminobiphenyl



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(0)

PlantCyc(0)

代谢反应

51 个相关的代谢反应过程信息。

Reactome(51)

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

  • Medjda Bellamri, Kyle Brandt, Christina V Brown, Ming-Tsang Wu, Robert J Turesky. Cytotoxicity and genotoxicity of the carcinogen aristolochic acid I (AA-I) in human bladder RT4 cells. Archives of toxicology. 2021 06; 95(6):2189-2199. doi: 10.1007/s00204-021-03059-3. [PMID: 33938965]
  • Jingshu Guo, Peter W Villalta, Christopher J Weight, Radha Bonala, Francis Johnson, Thomas A Rosenquist, Robert J Turesky. Targeted and Untargeted Detection of DNA Adducts of Aromatic Amine Carcinogens in Human Bladder by Ultra-Performance Liquid Chromatography-High-Resolution Mass Spectrometry. Chemical research in toxicology. 2018 12; 31(12):1382-1397. doi: 10.1021/acs.chemrestox.8b00268. [PMID: 30387604]
  • Byeong Hwa Yun, Medjda Bellamri, Thomas A Rosenquist, Robert J Turesky. Method for Biomonitoring DNA Adducts in Exfoliated Urinary Cells by Mass Spectrometry. Analytical chemistry. 2018 08; 90(16):9943-9950. doi: 10.1021/acs.analchem.8b02170. [PMID: 30001485]
  • Daniel Hanna, Ariane Emami Riedmaier, Kim S Sugamori, Denis M Grant. Influence of sex and developmental stage on acute hepatotoxic and inflammatory responses to liver procarcinogens in the mouse. Toxicology. 2016 Dec; 373(?):30-40. doi: 10.1016/j.tox.2016.10.006. [PMID: 27746196]
  • Shuang Wang, Debbie Bott, Aveline Tung, Kim S Sugamori, Denis M Grant. Relative Contributions of CYP1A2 and CYP2E1 to the Bioactivation and Clearance of 4-Aminobiphenyl in Adult Mice. Drug metabolism and disposition: the biological fate of chemicals. 2015 Jul; 43(7):916-21. doi: 10.1124/dmd.115.063297. [PMID: 25922528]
  • Arup Bhattacharya, Joshua J Klaene, Yun Li, Joseph D Paonessa, Aimee B Stablewski, Paul Vouros, Yuesheng Zhang. The inverse relationship between bladder and liver in 4-aminobiphenyl-induced DNA damage. Oncotarget. 2015 Jan; 6(2):836-45. doi: 10.18632/oncotarget.2722. [PMID: 25596734]
  • Hyun-Wook Lee, Hsiang-Tsui Wang, Mao-wen Weng, Yu Hu, Wei-sheng Chen, David Chou, Yan Liu, Nicholas Donin, William C Huang, Herbert Lepor, Xue-Ru Wu, Hailin Wang, Frederick A Beland, Moon-shong Tang. Acrolein- and 4-Aminobiphenyl-DNA adducts in human bladder mucosa and tumor tissue and their mutagenicity in human urothelial cells. Oncotarget. 2014 Jun; 5(11):3526-40. doi: 10.18632/oncotarget.1954. [PMID: 24939871]
  • Gerhard Scherer, Kirk Newland, Ermioni Papadopoulou, Emmanuel Minet. A correlation study applied to biomarkers of internal and effective dose for acrylonitrile and 4-aminobiphenyl in smokers. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2014 Jun; 19(4):291-301. doi: 10.3109/1354750x.2014.910271. [PMID: 24754403]
  • Jingjing Yu, Sheng Wang, Ge Zhao, Bing Wang, Li Ding, Xiaobing Zhang, Jianping Xie, Fuwei Xie. Determination of urinary aromatic amines in smokers and nonsmokers using a MIPs-SPE coupled with LC-MS/MS method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 May; 958(?):130-5. doi: 10.1016/j.jchromb.2014.03.023. [PMID: 24735928]
  • Lori M Millner, Mark A Doll, Jian Cai, J Christopher States, David W Hein. NATb/NAT1*4 promotes greater arylamine N-acetyltransferase 1 mediated DNA adducts and mutations than NATa/NAT1*4 following exposure to 4-aminobiphenyl. Molecular carcinogenesis. 2012 Aug; 51(8):636-46. doi: 10.1002/mc.20836. [PMID: 21837760]
  • Jae-In Yoon, Sang-In Kim, Stella Tommasi, Ahmad Besaratinia. Organ specificity of the bladder carcinogen 4-aminobiphenyl in inducing DNA damage and mutation in mice. Cancer prevention research (Philadelphia, Pa.). 2012 Feb; 5(2):299-308. doi: 10.1158/1940-6207.capr-11-0309. [PMID: 22086680]
  • Juan Alguacil, Manolis Kogevinas, Debra T Silverman, Núria Malats, Francisco X Real, Montserrat García-Closas, Adonina Tardón, Manuel Rivas, Montserrat Torà, Reina García-Closas, Consol Serra, Alfredo Carrato, Ruth M Pfeiffer, Joan Fortuny, Claudine Samanic, Nathaniel Rothman. Urinary pH, cigarette smoking and bladder cancer risk. Carcinogenesis. 2011 Jun; 32(6):843-7. doi: 10.1093/carcin/bgr048. [PMID: 21402590]
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  • Tiffany H Seyler, John T Bernert. Analysis of 4-aminobiphenyl in smoker's and nonsmoker's urine by tandem mass spectrometry. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2011 May; 16(3):212-21. doi: 10.3109/1354750x.2010.544755. [PMID: 21438718]
  • J G Hengstler, H Foth, T Gebel, P-J Kramer, W Lilienblum, H Schweinfurth, W Völkel, K-M Wollin, U Gundert-Remy. Critical evaluation of key evidence on the human health hazards of exposure to bisphenol A. Critical reviews in toxicology. 2011 Apr; 41(4):263-91. doi: 10.3109/10408444.2011.558487. [PMID: 21438738]
  • Thomas Schettgen, K Heinrich, T Kraus, Monika Gube. Determination of 2,5-toluylenediamine (2,5-TDA) and aromatic amines in urine after personal application of hair dyes: kinetics and doses. Archives of toxicology. 2011 Feb; 85(2):127-33. doi: 10.1007/s00204-010-0563-3. [PMID: 20549195]
  • Nilusha Ragunathan, Julien Dairou, Elodie Sanfins, Florent Busi, Christophe Noll, Nathalie Janel, Jean-Marie Dupret, Fernando Rodrigues-Lima. Cadmium alters the biotransformation of carcinogenic aromatic amines by arylamine N-acetyltransferase xenobiotic-metabolizing enzymes: molecular, cellular, and in vivo studies. Environmental health perspectives. 2010 Dec; 118(12):1685-91. doi: 10.1289/ehp.1002334. [PMID: 20810355]
  • Tiffany H Seyler, Levi-Rose Reyes, John T Bernert. Analysis of 4-aminobiphenyl hemoglobin adducts in smokers and nonsmokers by pseudo capillary on-column gas chromatography- tandem mass spectrometry. Journal of analytical toxicology. 2010 Jul; 34(6):304-11. doi: 10.1093/jat/34.6.304. [PMID: 20663282]
  • John H Warner, Qiwei Liang, Mohamadi Sarkar, Paul E Mendes, Hans J Roethig. Adaptive regression modeling of biomarkers of potential harm in a population of U.S. adult cigarette smokers and nonsmokers. BMC medical research methodology. 2010 Mar; 10(?):19. doi: 10.1186/1471-2288-10-19. [PMID: 20233412]
  • Ki Youn Kim, Jae Hoon Roh, Se Hoon Lee, Jong Uk Won, Chi Nyon Kim. Effects of ethanol and phenobarbital on hemoglobin adducts formation in rats exposed to benzidine and Direct Black 38. Industrial health. 2009 Aug; 47(4):383-92. doi: 10.2486/indhealth.47.383. [PMID: 19672012]
  • Mieke J J Van Hemelrijck, Dominique S Michaud, Gregory N Connolly, Zubair Kabir. Secondhand smoking, 4-aminobiphenyl, and bladder cancer: two meta-analyses. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2009 Apr; 18(4):1312-20. doi: 10.1158/1055-9965.epi-08-0613. [PMID: 19336562]
  • Maura Lodovici, Elisabetta Bigagli. Biomarkers of induced active and passive smoking damage. International journal of environmental research and public health. 2009 03; 6(3):874-88. doi: 10.3390/ijerph6030874. [PMID: 19440419]
  • Erin E Bessette, Angela K Goodenough, Sophie Langouët, Isil Yasa, Ivan D Kozekov, Simon D Spivack, Robert J Turesky. Screening for DNA adducts by data-dependent constant neutral loss-triple stage mass spectrometry with a linear quadrupole ion trap mass spectrometer. Analytical chemistry. 2009 Jan; 81(2):809-19. doi: 10.1021/ac802096p. [PMID: 19086795]
  • David W Hein, Jean Bendaly, Jason R Neale, Mark A Doll. Systemic functional expression of N-acetyltransferase polymorphism in the F344 Nat2 congenic rat. Drug metabolism and disposition: the biological fate of chemicals. 2008 Dec; 36(12):2452-9. doi: 10.1124/dmd.108.023960. [PMID: 18799801]
  • Vikas Kumar, Chandrajeetbalo Majumdar, Partha Roy. Effects of endocrine disrupting chemicals from leather industry effluents on male reproductive system. The Journal of steroid biochemistry and molecular biology. 2008 Sep; 111(3-5):208-16. doi: 10.1016/j.jsbmb.2008.06.005. [PMID: 18606229]
  • Amit Bafana, Kannan Krishnamurthi, Sivanesan Saravana Devi, Tapan Chakrabarti. Biological decolourization of C.I. Direct Black 38 by E. gallinarum. Journal of hazardous materials. 2008 Aug; 157(1):187-93. doi: 10.1016/j.jhazmat.2007.12.085. [PMID: 18280646]
  • J W M Yuen, M D I Gohel. The dual roles of Ganoderma antioxidants on urothelial cell DNA under carcinogenic attack. Journal of ethnopharmacology. 2008 Jul; 118(2):324-30. doi: 10.1016/j.jep.2008.05.003. [PMID: 18550308]
  • Hans J Roethig, Shixia Feng, Qiwei Liang, Jianmin Liu, William A Rees, Barbara K Zedler. A 12-month, randomized, controlled study to evaluate exposure and cardiovascular risk factors in adult smokers switching from conventional cigarettes to a second-generation electrically heated cigarette smoking system. Journal of clinical pharmacology. 2008 May; 48(5):580-91. doi: 10.1177/0091270008315316. [PMID: 18319361]
  • Patrudu Makena, King-Thom Chung. Evidence that 4-aminobiphenyl, benzidine, and benzidine congeners produce genotoxicity through reactive oxygen species. Environmental and molecular mutagenesis. 2007 Jun; 48(5):404-13. doi: 10.1002/em.20288. [PMID: 17370336]
  • Amit Bafana, Sivanesan Saravana Devi, Kannan Krishnamurthi, Tapan Chakrabarti. Kinetics of decolourisation and biotransformation of direct black 38 by C. hominis and P. stutzeri. Applied microbiology and biotechnology. 2007 Apr; 74(5):1145-52. doi: 10.1007/s00253-006-0751-5. [PMID: 17318544]
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  • Mustafa Al-Zoughool, Paul Succop, Pankaj Desai, Jay Vietas, Glenn Talaska. Effect of N-glucuronidation on urinary bladder genotoxicity of 4-aminobiphenyl in male and female mice. Environmental toxicology and pharmacology. 2006 Sep; 22(2):153-9. doi: 10.1016/j.etap.2006.02.002. [PMID: 21783703]
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  • Paul L Skipper, Laura J Trudel, Thomas W Kensler, John D Groopman, Patricia A Egner, Rosa G Liberman, Gerald N Wogan, Steven R Tannenbaum. DNA adduct formation by 2,6-dimethyl-, 3,5-dimethyl-, and 3-ethylaniline in vivo in mice. Chemical research in toxicology. 2006 Aug; 19(8):1086-90. doi: 10.1021/tx060082q. [PMID: 16918249]
  • Kirsten Riedel, Gerhard Scherer, Johannes Engl, Heinz-Werner Hagedorn, Anthony R Tricker. Determination of three carcinogenic aromatic amines in urine of smokers and nonsmokers. Journal of analytical toxicology. 2006 Apr; 30(3):187-95. doi: 10.1093/jat/30.3.187. [PMID: 16803653]
  • John T Bernert, Ram B Jain, James L Pirkle, Lanqing Wang, Barbara B Miller, Eric J Sampson. Urinary tobacco-specific nitrosamines and 4-aminobiphenyl hemoglobin adducts measured in smokers of either regular or light cigarettes. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2005 Oct; 7(5):729-38. doi: 10.1080/14622200500259762. [PMID: 16191744]
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  • Qing-Yi Lu, Yu-Sheng Jin, Allan Pantuck, Zuo-Feng Zhang, David Heber, Arie Belldegrun, Mai Brooks, Robert Figlin, Jianyu Rao. Green tea extract modulates actin remodeling via Rho activity in an in vitro multistep carcinogenic model. Clinical cancer research : an official journal of the American Association for Cancer Research. 2005 Feb; 11(4):1675-83. doi: 10.1158/1078-0432.ccr-04-1608. [PMID: 15746073]
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