5-Hydroxymethyl-2-deoxyuridine (BioDeep_00000790555)

   


代谢物信息卡片


5-Hydroxymethyl-2-deoxyuridine

  化学式: C10H14N2O6 (258.0852)
中文名称: 5-羟甲基-2-脱氧尿苷
  谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)CO)CO)O
InChI: InChI=1S/C10H14N2O6/c13-3-5-2-12(10(17)11-9(5)16)8-1-6(15)7(4-14)18-8/h2,6-8,13-15H,1,3-4H2,(H,11,16,17)/t6-,7+,8+/m0/s1


描述信息

D000970 - Antineoplastic Agents
5-Hydroxymethyl-2'-deoxyuridine is a nucleoside analog. 5-Hydroxymethyl-2'-deoxyuridine inhibits the replication of multiple human leukemia cell lines with IC50 values of 1.7-5.8 μM. 5-Hydroxymethyl-2'-deoxyuridine prolongs the survival of mice carrying L1210 leukemia. 5-Hydroxymethyl-2'-deoxyuridine can be used for the research of cell replication and leukemia[1][2][3].

同义名列表

2 个代谢物同义名

5-Hydroxymethyl-2-deoxyuridine; 5-Hydroxymethyl-2'-deoxyuridine



数据库引用编号

5 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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INOH(0)

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COVID-19 Disease Map(0)

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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。

亚细胞结构定位 关联基因列表


文献列表

  • Shuo Liu, Thomas L Dunwell, Gerd P Pfeifer, Jim M Dunwell, Ihsan Ullah, Yinsheng Wang. Detection of oxidation products of 5-methyl-2'-deoxycytidine in Arabidopsis DNA. PloS one. 2013; 8(12):e84620. doi: 10.1371/journal.pone.0084620. [PMID: 24391970]
  • Lisa S McAnulty, David C Nieman, Charles L Dumke, Lesli A Shooter, Dru A Henson, Alan C Utter, Ginger Milne, Steven R McAnulty. Effect of blueberry ingestion on natural killer cell counts, oxidative stress, and inflammation prior to and after 2.5 h of running. Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme. 2011 Dec; 36(6):976-84. doi: 10.1139/h11-120. [PMID: 22111516]
  • Sung-Hee Cho, Man Ho Choi, Won-Yong Lee, Bong Chul Chung. Evaluation of urinary nucleosides in breast cancer patients before and after tumor removal. Clinical biochemistry. 2009 Apr; 42(6):540-3. doi: 10.1016/j.clinbiochem.2008.12.026. [PMID: 19186175]
  • Sung-Hee Cho, Man Ho Choi, Oh Seung Kwon, Won-Yong Lee, Bong Chul Chung. Metabolic significance of bisphenol A-induced oxidative stress in rat urine measured by liquid chromatography-mass spectrometry. Journal of applied toxicology : JAT. 2009 Mar; 29(2):110-7. doi: 10.1002/jat.1387. [PMID: 18980270]
  • Anne Zeleniuch-Jacquotte, Qi Zhang, Jisen Dai, Roy E Shore, Alan A Arslan, Karen L Koenig, Jerzy Karkoszka, Yelena Afanasyeva, Krystyna Frenkel, Paolo Toniolo, Xi Huang. Reliability of serum assays of iron status in postmenopausal women. Annals of epidemiology. 2007 May; 17(5):354-8. doi: 10.1016/j.annepidem.2006.07.004. [PMID: 17027294]
  • I Kato, J Ren, L K Heilbrun, Zora Djuric. Intra- and inter-individual variability in measurements of biomarkers for oxidative damage in vivo: Nutrition and Breast Health Study. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2006 Mar; 11(2):143-52. doi: 10.1080/13547500600565693. [PMID: 16766390]
  • Somdat Mahabir, Krystyna Frenkel, Mary Sue Brady, Daniel Coit, Leonard Leibes, Jerzy Karkoszka, Marianne Berwick. Randomized, placebo-controlled pilot trial of the effects of alpha-tocopherol supplementation on levels of autoantibodies against 5-hydroxymethyl-2-deoxyuridine in melanoma patients. Melanoma research. 2004 Feb; 14(1):49-56. doi: 10.1097/00008390-200402000-00008. [PMID: 15091194]
  • S Mitchell Harman, Lynn Liang, Panayiotis D Tsitouras, Frank Gucciardo, Christopher B Heward, Peter D Reaven, Wei Ping, Alaa Ahmed, Richard G Cutler. Urinary excretion of three nucleic acid oxidation adducts and isoprostane F(2)alpha measured by liquid chromatography-mass spectrometry in smokers, ex-smokers, and nonsmokers. Free radical biology & medicine. 2003 Nov; 35(10):1301-9. doi: 10.1016/j.freeradbiomed.2003.07.003. [PMID: 14607529]
  • Peter Wallström, Krystyna Frenkel, Elisabet Wirfält, Bo Gullberg, Jerzy Karkoszka, Janeric Seidegård, Lars Janzon, Göran Berglund. Antibodies against 5-hydroxymethyl-2'-deoxyuridine are associated with lifestyle factors and GSTM1 genotype: a report from the Malmö Diet and Cancer cohort. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2003 May; 12(5):444-51. doi: NULL. [PMID: 12750240]
  • Omer Kucuk, Fazlul H Sarkar, Zora Djuric, Wael Sakr, Michael N Pollak, Fred Khachik, Mousumi Banerjee, John S Bertram, David P Wood. Effects of lycopene supplementation in patients with localized prostate cancer. Experimental biology and medicine (Maywood, N.J.). 2002 Nov; 227(10):881-5. doi: 10.1177/153537020222701007. [PMID: 12424329]
  • R V Cooney, G Maskarinec, A A Franke, L Okinaka, J Karkoszka, L R Wilkens, K Frenkel. Association of tocopherols with circulating autoantibody levels against an oxidized DNA nucleoside in humans. Free radical biology & medicine. 2001 Aug; 31(4):460-8. doi: 10.1016/s0891-5849(01)00606-2. [PMID: 11498279]
  • L A Mooney, F P Perera, A M Van Bennekum, W S Blaner, J Karkoszka, L Covey, Y Hsu, T B Cooper, K Frenkel. Gender differences in autoantibodies to oxidative DNA base damage in cigarette smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2001 Jun; 10(6):641-8. doi: NULL. [PMID: 11401914]
  • Z Djuric, D W Potter, B G Taffe, G M Strasburg. Comparison of iron-catalyzed DNA and lipid oxidation. Journal of biochemical and molecular toxicology. 2001; 15(2):114-9. doi: 10.1002/jbt.7. [PMID: 11284053]
  • K Frenkel, J Karkoszka, T Glassman, N Dubin, P Toniolo, E Taioli, L A Mooney, I Kato. Serum autoantibodies recognizing 5-hydroxymethyl-2'-deoxyuridine, an oxidized DNA base, as biomarkers of cancer risk in women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1998 Jan; 7(1):49-57. doi: NULL. [PMID: 9456243]
  • A J Teixeira, M R Ferreira, W J van Dijk, G van de Werken, A P de Jong. Analysis of 8-hydroxy-2'-deoxyguanosine in rat urine and liver DNA by stable isotope dilution gas chromatography/mass spectrometry. Analytical biochemistry. 1995 Apr; 226(2):307-19. doi: 10.1006/abio.1995.1230. [PMID: 7793633]
  • A J Teixeira, J H Gommers-Ampt, G Van de Werken, J G Westra, J F Stavenuiter, A P de Jong. Method for the analysis of oxidized nucleosides by gas chromatography/mass spectrometry. Analytical biochemistry. 1993 Nov; 214(2):474-83. doi: 10.1006/abio.1993.1525. [PMID: 8109736]
  • K Frenkel, J Karkoszka, E Kim, E Taioli. Recognition of oxidized DNA bases by sera of patients with inflammatory diseases. Free radical biology & medicine. 1993 May; 14(5):483-94. doi: 10.1016/0891-5849(93)90105-4. [PMID: 8349138]
  • K Frenkel, D Khasak, J Karkoszka, J Shupack, M Stiller. Enhanced antibody titers to an oxidized DNA base in inflammatory and neoplastic diseases. Experimental dermatology. 1992 Dec; 1(5):242-7. doi: 10.1111/j.1600-0625.1992.tb00083.x. [PMID: 1365325]
  • K Frenkel. Oxidation of DNA bases by tumor promoter-activated processes. Environmental health perspectives. 1989 May; 81(?):45-54. doi: 10.1289/ehp.898145. [PMID: 2667984]
  • J A Vilpo, E Suvanto, S Rasi, L M Vilpo. Radioimmunoassay of 5-hydroxymethyl-2'-deoxyuridine. Journal of immunological methods. 1987 Oct; 103(1):41-5. doi: 10.1016/0022-1759(87)90239-0. [PMID: 3655385]
  • J A Vilpo, E Suvanto, L Kangas. Antileukemic activity against L1210 leukemia, pharmacokinetics and hematological side effects of 5-hydroxymethyl-2'-deoxyuridine. Leukemia research. 1987; 11(10):877-80. doi: 10.1016/0145-2126(87)90132-9. [PMID: 3682866]
  • K Frenkel, K Chrzan, W Troll, G W Teebor, J J Steinberg. Radiation-like modification of bases in DNA exposed to tumor promoter-activated polymorphonuclear leukocytes. Cancer research. 1986 Nov; 46(11):5533-40. doi: NULL. [PMID: 3756901]
  • J Reefschläger, D Brwolff, D Bärwolff, P Langen, H A Rosenthal. Efficiency and selectivity of (E)-5-(2-bromovinyl)-2'-deoxyuridine and some other 5-substituted 2'-deoxypyrimidine nucleosides as anti-herpes agents. Antiviral research. 1982 May; 2(1-2):41-52. doi: 10.1016/0166-3542(82)90025-0. [PMID: 6285818]
  • H L Lewis, D R Muhleman, J F Ward. Serologic assay of DNA base damage. I. 5-Hydroxymethyldeoxyuridine, a radiation product of thymidine. Radiation research. 1978 Aug; 75(2):305-16. doi: 10.2307/3574906. [PMID: 568811]