1,N6-Ethenoadenine (BioDeep_00000172514)

   

human metabolite blood metabolite


代谢物信息卡片


3H-imidazo[2,1-f]purine

化学式: C7H5N5 (159.054493)
中文名称: 1,N⁶-乙基腺嘌呤
谱图信息: 最多检出来源 Homo sapiens(blood) 0.25%

分子结构信息

SMILES: C1=CN2C=NC3=C(C2=N1)NC=N3
InChI: InChI=1S/C7H5N5/c1-2-12-4-11-6-5(7(12)8-1)9-3-10-6/h1-4H,(H,9,10)

描述信息

D009676 - Noxae > D009153 - Mutagens

同义名列表

6 个代谢物同义名

3H-imidazo[2,1-f]purine; 3H-imidazo[2,1-i]purine; 1,N(6)-Ethenoadenine; EpsilonA nucleobase; 1,N6-ETHENOADENINE; Ethenoadenine



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(1)

BioCyc(0)

PlantCyc(0)

代谢反应

65 个相关的代谢反应过程信息。

Reactome(65)

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

  • Katelyn L Rioux, Sarah Delaney. 1,N6-Ethenoadenine: From Molecular to Biological Consequences†. Chemical research in toxicology. 2020 11; 33(11):2688-2698. doi: 10.1021/acs.chemrestox.0c00326. [PMID: 33112144]
  • Isaac A Chaim, Alycia Gardner, Jie Wu, Teruaki Iyama, David M Wilson, Leona D Samson. A novel role for transcription-coupled nucleotide excision repair for the in vivo repair of 3,N4-ethenocytosine. Nucleic acids research. 2017 04; 45(6):3242-3252. doi: 10.1093/nar/gkx015. [PMID: 28115629]
  • Alicja Winczura, Alicja Czubaty, Kinga Winczura, Katarzyna Masłowska, Matylda Nałęcz, Dominika A Dudzińska, Murat Saparbaev, Krzysztof Staroń, Barbara Tudek. Lipid peroxidation product 4-hydroxy-2-nonenal modulates base excision repair in human cells. DNA repair. 2014 Oct; 22(?):1-11. doi: 10.1016/j.dnarep.2014.06.002. [PMID: 25083554]
  • Jordan Woodrick, Suhani Gupta, Pooja Khatkar, Sanchita Sarangi, Ganga Narasimhan, Akriti Trehan, Sanjay Adhikari, Rabindra Roy. Slow repair of lipid peroxidation-induced DNA damage at p53 mutation hotspots in human cells caused by low turnover of a DNA glycosylase. Nucleic acids research. 2014 Aug; 42(14):9033-46. doi: 10.1093/nar/gku520. [PMID: 25081213]
  • Chengqi Yi, Baoen Chen, Bo Qi, Wen Zhang, Guifang Jia, Liang Zhang, Charles J Li, Aaron R Dinner, Cai-Guang Yang, Chuan He. Duplex interrogation by a direct DNA repair protein in search of base damage. Nature structural & molecular biology. 2012 Jun; 19(7):671-6. doi: 10.1038/nsmb.2320. [PMID: 22659876]
  • Paulina Prorok, Christine Saint-Pierre, Didier Gasparutto, Olga S Fedorova, Alexander A Ishchenko, Hervé Leh, Malcolm Buckle, Barbara Tudek, Murat Saparbaev. Highly mutagenic exocyclic DNA adducts are substrates for the human nucleotide incision repair pathway. PloS one. 2012; 7(12):e51776. doi: 10.1371/journal.pone.0051776. [PMID: 23251620]
  • Nicole Berdelle, Teodora Nikolova, Steve Quiros, Thomas Efferth, Bernd Kaina. Artesunate induces oxidative DNA damage, sustained DNA double-strand breaks, and the ATM/ATR damage response in cancer cells. Molecular cancer therapeutics. 2011 Dec; 10(12):2224-33. doi: 10.1158/1535-7163.mct-11-0534. [PMID: 21998290]
  • Tomasz Obtułowicz, Alicja Winczura, Elzbieta Speina, Maja Swoboda, Justyna Janik, Beata Janowska, Jarosław M Cieśla, Paweł Kowalczyk, Arkadiusz Jawien, Daniel Gackowski, Zbigniew Banaszkiewicz, Ireneusz Krasnodebski, Andrzej Chaber, Ryszard Olinski, Jagadesaan Nair, Helmut Bartsch, Thierry Douki, Jean Cadet, Barbara Tudek. Aberrant repair of etheno-DNA adducts in leukocytes and colon tissue of colon cancer patients. Free radical biology & medicine. 2010 Sep; 49(6):1064-71. doi: 10.1016/j.freeradbiomed.2010.06.027. [PMID: 20600828]
  • Somkid Dechakhamphu, Somchai Pinlaor, Paiboon Sitthithaworn, Helmut Bartsch, Puangrat Yongvanit. Accumulation of miscoding etheno-DNA adducts and highly expressed DNA repair during liver fluke-induced cholangiocarcinogenesis in hamsters. Mutation research. 2010 Sep; 691(1-2):9-16. doi: 10.1016/j.mrfmmm.2010.06.003. [PMID: 20541562]
  • Barbara Tudek, Alicja Winczura, Justyna Janik, Agnieszka Siomek, Marek Foksinski, Ryszard Oliński. Involvement of oxidatively damaged DNA and repair in cancer development and aging. American journal of translational research. 2010 May; 2(3):254-84. doi: ". [PMID: 20589166]
  • Dolores Córdoba-Cañero, Teresa Morales-Ruiz, Teresa Roldán-Arjona, Rafael R Ariza. Single-nucleotide and long-patch base excision repair of DNA damage in plants. The Plant journal : for cell and molecular biology. 2009 Nov; 60(4):716-28. doi: 10.1111/j.1365-313x.2009.03994.x. [PMID: 19682284]
  • Sanjay Adhikari, Aykut Uren, Rabindra Roy. Excised damaged base determines the turnover of human N-methylpurine-DNA glycosylase. DNA repair. 2009 Oct; 8(10):1201-6. doi: 10.1016/j.dnarep.2009.06.005. [PMID: 19616486]
  • Charles G Knutson, Emily H Rubinson, Dapo Akingbade, Carolyn S Anderson, Donald F Stec, Katya V Petrova, Ivan D Kozekov, F Peter Guengerich, Carmelo J Rizzo, Lawrence J Marnett. Oxidation and glycolytic cleavage of etheno and propano DNA base adducts. Biochemistry. 2009 Feb; 48(4):800-9. doi: 10.1021/bi801654j. [PMID: 19132922]
  • Laureen C Colis, Paromita Raychaudhury, Ashis K Basu. Mutational specificity of gamma-radiation-induced guanine-thymine and thymine-guanine intrastrand cross-links in mammalian cells and translesion synthesis past the guanine-thymine lesion by human DNA polymerase eta. Biochemistry. 2008 Aug; 47(31):8070-9. doi: 10.1021/bi800529f. [PMID: 18616294]
  • Sujata Choudhury, Sanjay Adhikari, Amrita Cheema, Rabindra Roy. Evidence of complete cellular repair of 1,N6-ethenoadenine, a mutagenic and potential damage for human cancer, revealed by a novel method. Molecular and cellular biochemistry. 2008 Jun; 313(1-2):19-28. doi: 10.1007/s11010-008-9737-1. [PMID: 18373235]
  • Jeanette Ringvoll, Marivi N Moen, Line M Nordstrand, Lisiane B Meira, Bo Pang, Anders Bekkelund, Peter C Dedon, Svein Bjelland, Leona D Samson, Pål Ø Falnes, Arne Klungland. AlkB homologue 2-mediated repair of ethenoadenine lesions in mammalian DNA. Cancer research. 2008 Jun; 68(11):4142-9. doi: 10.1158/0008-5472.can-08-0796. [PMID: 18519673]
  • Barbara Tudek. Base excision repair modulation as a risk factor for human cancers. Molecular aspects of medicine. 2007 Jun; 28(3-4):258-75. doi: 10.1016/j.mam.2007.05.003. [PMID: 17628657]
  • Hauh-Jyun Candy Chen, Chi-Fu Kao. Effect of gender and cigarette smoking on urinary excretion of etheno DNA adducts in humans measured by isotope dilution gas chromatography/mass spectrometry. Toxicology letters. 2007 Feb; 169(1):72-81. doi: 10.1016/j.toxlet.2006.12.005. [PMID: 17241756]
  • Sanjay Adhikari, Jeffery A Toretsky, Linshan Yuan, Rabindra Roy. Magnesium, essential for base excision repair enzymes, inhibits substrate binding of N-methylpurine-DNA glycosylase. The Journal of biological chemistry. 2006 Oct; 281(40):29525-32. doi: 10.1074/jbc.m602673200. [PMID: 16901897]
  • James C Delaney, Lisa Smeester, Cintyu Wong, Lauren E Frick, Koli Taghizadeh, John S Wishnok, Catherine L Drennan, Leona D Samson, John M Essigmann. AlkB reverses etheno DNA lesions caused by lipid oxidation in vitro and in vivo. Nature structural & molecular biology. 2005 Oct; 12(10):855-60. doi: 10.1038/nsmb996. [PMID: 16200073]
  • Hermann M Bolt. Vinyl chloride-a classical industrial toxicant of new interest. Critical reviews in toxicology. 2005 Apr; 35(4):307-23. doi: 10.1080/10408440490915975. [PMID: 15989139]
  • Hauh-Jyun Candy Chen, Chan-Fu Wu, Ju-Li Huang. Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS: correlation with cigarette smoking, urinary TBARS and etheno DNA adduct. Toxicology letters. 2005 Mar; 155(3):403-10. doi: 10.1016/j.toxlet.2004.11.009. [PMID: 15649624]
  • Hauh-Jyun Candy Chen, Chia-Ming Chang. Quantification of urinary excretion of 1,N6-ethenoadenine, a potential biomarker of lipid peroxidation, in humans by stable isotope dilution liquid chromatography-electrospray ionization-tandem mass spectrometry: comparison with gas chromatography-mass spectrometry. Chemical research in toxicology. 2004 Jul; 17(7):963-71. doi: 10.1021/tx0341963. [PMID: 15257622]
  • Thierry Douki, Francette Odin, Sylvain Caillat, Alain Favier, Jean Cadet. Predominance of the 1,N2-propano 2'-deoxyguanosine adduct among 4-hydroxy-2-nonenal-induced DNA lesions. Free radical biology & medicine. 2004 Jul; 37(1):62-70. doi: 10.1016/j.freeradbiomed.2004.04.013. [PMID: 15183195]
  • Laurent Gros, Andrei V Maksimenko, Cyril V Privezentzev, Jacques Laval, Murat K Saparbaev. Hijacking of the human alkyl-N-purine-DNA glycosylase by 3,N4-ethenocytosine, a lipid peroxidation-induced DNA adduct. The Journal of biological chemistry. 2004 Apr; 279(17):17723-30. doi: 10.1074/jbc.m314010200. [PMID: 14761949]
  • Alain Barbin, Rong Wang, Peter J O'Connor, Rhoderick H Elder. Increased formation and persistence of 1,N(6)-ethenoadenine in DNA is not associated with higher susceptibility to carcinogenesis in alkylpurine-DNA-N-glycosylase knockout mice treated with vinyl carbamate. Cancer research. 2003 Nov; 63(22):7699-703. doi: ". [PMID: 14633693]
  • Helena Plchova, Frank Hartung, Holger Puchta. Biochemical characterization of an exonuclease from Arabidopsis thaliana reveals similarities to the DNA exonuclease of the human Werner syndrome protein. The Journal of biological chemistry. 2003 Nov; 278(45):44128-38. doi: 10.1074/jbc.m303891200. [PMID: 12937173]
  • Laurent Gros, Alexander A Ishchenko, Murat Saparbaev. Enzymology of repair of etheno-adducts. Mutation research. 2003 Oct; 531(1-2):219-29. doi: 10.1016/j.mrfmmm.2003.07.008. [PMID: 14637257]
  • Elzbieta Speina, Andrzej M Kierzek, Barbara Tudek. Chemical rearrangement and repair pathways of 1,N6-ethenoadenine. Mutation research. 2003 Oct; 531(1-2):205-17. doi: 10.1016/j.mrfmmm.2003.07.007. [PMID: 14637256]
  • Lutz Sternfeld, Elmar Krause, Andreas H Guse, Irene Schulz. Hormonal control of ADP-ribosyl cyclase activity in pancreatic acinar cells from rats. The Journal of biological chemistry. 2003 Sep; 278(36):33629-36. doi: 10.1074/jbc.m301043200. [PMID: 12807891]
  • Hauh-Jyun Candy Chen, Wei-Loong Chiu. Detection and quantification of 1,N6-ethenoadenine in human urine by stable isotope dilution capillary gas chromatography/negative ion chemical ionization/mass spectrometry. Chemical research in toxicology. 2003 Sep; 16(9):1099-106. doi: 10.1021/tx034057l. [PMID: 12971797]
  • Elzbieta Speina, Maja Zielińska, Alain Barbin, Daniel Gackowski, Janusz Kowalewski, Maria A Graziewicz, Janusz A Siedlecki, Ryszard Oliński, Barbara Tudek. Decreased repair activities of 1,N(6)-ethenoadenine and 3,N(4)-ethenocytosine in lung adenocarcinoma patients. Cancer research. 2003 Aug; 63(15):4351-7. doi: ". [PMID: 12907604]
  • Murat Saparbaev, Sophie Langouët, Cyril V Privezentzev, F Peter Guengerich, Hongliang Cai, Rhoderick H Elder, Jacques Laval. 1,N(2)-ethenoguanine, a mutagenic DNA adduct, is a primary substrate of Escherichia coli mismatch-specific uracil-DNA glycosylase and human alkylpurine-DNA-N-glycosylase. The Journal of biological chemistry. 2002 Jul; 277(30):26987-93. doi: 10.1074/jbc.m111100200. [PMID: 12016206]
  • K S Tanaka, X Y Chen, Y Ichikawa, P C Tyler, R H Furneaux, V L Schramm. Ricin A-chain inhibitors resembling the oxacarbenium ion transition state. Biochemistry. 2001 Jun; 40(23):6845-51. doi: 10.1021/bi010499p. [PMID: 11389598]
  • H J Chen, L C Chiang, M C Tseng, L L Zhang, J Ni, F L Chung. Detection and quantification of 1,N(6)-ethenoadenine in human placental DNA by mass spectrometry. Chemical research in toxicology. 1999 Dec; 12(12):1119-26. doi: 10.1021/tx990074s. [PMID: 10604859]
  • M Saparbaev, J Laval. Enzymology of the repair of etheno adducts in mammalian cells and in Escherichia coli. IARC scientific publications. 1999; ?(150):249-61. doi: ". [PMID: 10626225]
  • A K Basu, J M McNulty, W G McGregor. Solution conformation and mutagenic specificity of 1,N6-ethenoadenine. IARC scientific publications. 1999; ?(150):325-33. doi: NULL. [PMID: 10626232]
  • A Barbin. Role of etheno DNA adducts in carcinogenesis induced by vinyl chloride in rats. IARC scientific publications. 1999; ?(150):303-13. doi: NULL. [PMID: 10626230]
  • S Holt, T Y Yen, R Sangaiah, J A Swenberg. Detection of 1,N6-ethenoadenine in rat urine after chloroethylene oxide exposure. Carcinogenesis. 1998 Oct; 19(10):1763-9. doi: 10.1093/carcin/19.10.1763. [PMID: 9806156]
  • T Y Yen, S Holt, R Sangaiah, A Gold, J A Swenberg. Quantitation of 1,N6-ethenoadenine in rat urine by immunoaffinity extraction combined with liquid chromatography/electrospray ionization mass spectrometry. Chemical research in toxicology. 1998 Jul; 11(7):810-5. doi: 10.1021/tx9800194. [PMID: 9671544]
  • F el Ghissassi, A Barbin, J Nair, H Bartsch. Formation of 1,N6-ethenoadenine and 3,N4-ethenocytosine by lipid peroxidation products and nucleic acid bases. Chemical research in toxicology. 1995 Mar; 8(2):278-83. doi: 10.1021/tx00044a013. [PMID: 7766812]
  • L Naesens, J Balzarini, E De Clercq. Acyclic adenine nucleoside phosphonates in plasma determined by high-performance liquid chromatography with fluorescence detection. Clinical chemistry. 1992 Apr; 38(4):480-5. doi: 10.1093/clinchem/38.4.480. [PMID: 1568310]
  • S P Dutta, A Mittelman, G B Chheda. Metabolism of 1,N6-ethenoadenosine. Biochemical medicine. 1980 Apr; 23(2):179-84. doi: 10.1016/0006-2944(80)90069-1. [PMID: 7396887]