5-Fluorodeoxyuridine monophosphate (BioDeep_00000005454)

 

Secondary id: BioDeep_00001869631

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


{[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

化学式: C9H12FN2O8P (326.0315294)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 22.99%

分子结构信息

SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)F)COP(=O)(O)O)O
InChI: InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1

描述信息

5-Fluorodeoxyuridine monophosphate is a metabolite of floxuridine. Floxuridine (also 5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites. The drug is most often used in the treatment of colorectal cancer. (Wikipedia)

同义名列表

13 个代谢物同义名

{[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid; [(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3H-pyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid; 5-Fluoro-2-deoxyuridine monophosphoric acid (fdump); 5-Fluoro-2-deoxyuridine monophosphate (fdump); 5-Fluoro-2-deoxyuridine-5-monophosphoric acid; 5-Fluorodeoxyuridine monophosphoric acid; 5 Fluoro 2 deoxyuridine 5 monophosphate; 5-Fluoro-2-deoxyuridine-5-monophosphate; 5-Fluorodeoxyuridine monophosphate; 5-FLUORODEOXYURIDYLic acid; Fluorodeoxyuridylate; 5-Fluoro-dUMP; FdUMP



数据库引用编号

16 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

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

  • Weiran Cao, Xue Zhang, Rui Li, Zijie Li, An Lu, Fei Yu, Lu Sun, Jiancheng Wang, Zhiyu Wang, Huining He. Lipid core-shell nanoparticles co-deliver FOLFOX regimen and siPD-L1 for synergistic targeted cancer treatment. Journal of controlled release : official journal of the Controlled Release Society. 2024 Apr; 368(?):52-65. doi: 10.1016/j.jconrel.2024.02.025. [PMID: 38368946]
  • Jianfeng Guo, Leaf Huang. Formulation of two lipid-based membrane-core nanoparticles for FOLFOX combination therapy. Nature protocols. 2022 08; 17(8):1818-1831. doi: 10.1038/s41596-022-00698-3. [PMID: 35650451]
  • Jianfeng Guo, Zhuo Yu, Dandan Sun, Yifang Zou, Yun Liu, Leaf Huang. Two nanoformulations induce reactive oxygen species and immunogenetic cell death for synergistic chemo-immunotherapy eradicating colorectal cancer and hepatocellular carcinoma. Molecular cancer. 2021 01; 20(1):10. doi: 10.1186/s12943-020-01297-0. [PMID: 33407548]
  • R Arlanov, T Lang, G Jedlitschky, E Schaeffeler, T Ishikawa, M Schwab, A T Nies. Functional characterization of common protein variants in the efflux transporter ABCC11 and identification of T546M as functionally damaging variant. The pharmacogenomics journal. 2016 Apr; 16(2):193-201. doi: 10.1038/tpj.2015.27. [PMID: 25896536]
  • Carmen Eicher, Alexander Dewerth, Verena Ellerkamp, Joerg Fuchs, Sarah Schott, Sorin Armeanu-Ebinger. Effect of duplex drugs linking 2'-deoxy-5-fluorouridine (5-FdU) with 3'-C-ethynylcytidine (ECyd) on hepatoblastoma cell lines. Pediatric surgery international. 2013 Feb; 29(2):121-7. doi: 10.1007/s00383-012-3192-5. [PMID: 23187893]
  • Sarah Schott, Heike Niessner, Tobias Sinnberg, Sascha Venturelli, Alexander Berger, Kristian Ikenberg, Jessie Villanueva, Friedegund Meier, Claus Garbe, Christian Busch. Cytotoxicity of new duplex drugs linking 3'-C-ethynylcytidine and 5-fluor-2'-deoxyuridine against human melanoma cells. International journal of cancer. 2012 Nov; 131(9):2165-74. doi: 10.1002/ijc.27476. [PMID: 22323315]
  • Arun Chauhan, Swaleha Zubair, Asif Sherwani, Mohammad Owais. Aloe vera induced biomimetic assemblage of nucleobase into nanosized particles. PloS one. 2012; 7(3):e32049. doi: 10.1371/journal.pone.0032049. [PMID: 22403622]
  • Francisco Javier Fernández Acero, María Carbú, Mohamed Rabie El-Akhal, Carlos Garrido, Victoria E González-Rodríguez, Jesús M Cantoral. Development of proteomics-based fungicides: new strategies for environmentally friendly control of fungal plant diseases. International journal of molecular sciences. 2011 Jan; 12(1):795-816. doi: 10.3390/ijms12010795. [PMID: 21340014]
  • Masao Kobayakawa, Yasushi Kojima. Tegafur/gimeracil/oteracil (S-1) approved for the treatment of advanced gastric cancer in adults when given in combination with cisplatin: a review comparing it with other fluoropyrimidine-based therapies. OncoTargets and therapy. 2011; 4(?):193-201. doi: 10.2147/ott.s19059. [PMID: 22162925]
  • Yuan-Wan Sun, Kun-Ming Chen, Chul-Hoon Kwon. Sulfonyl-containing nucleoside phosphotriesters and phosphoramidates as novel anticancer prodrugs of 5-fluoro-2'-deoxyuridine 5'-monophosphate (FdUMP). Molecular pharmaceutics. 2006 Mar; 3(2):161-73. doi: 10.1021/mp0500622. [PMID: 16579645]
  • Susan Pratt, Robert L Shepard, Ramani A Kandasamy, Paul A Johnston, William Perry, Anne H Dantzig. The multidrug resistance protein 5 (ABCC5) confers resistance to 5-fluorouracil and transports its monophosphorylated metabolites. Molecular cancer therapeutics. 2005 May; 4(5):855-63. doi: 10.1158/1535-7163.mct-04-0291. [PMID: 15897250]
  • A Ravaud, N Trufflandier, J M Ferrière, M Debled, J Palussière, L Cany, R Gaston, S Mathoulin-Pélissier, B N Bui. Subcutaneous interleukin-2, interferon alpha-2b and 5-fluorouracil in metastatic renal cell carcinoma as second-line treatment after failure of previous immunotherapy: a phase II trial. British journal of cancer. 2003 Dec; 89(12):2213-8. doi: 10.1038/sj.bjc.6601419. [PMID: 14676797]
  • Masaaki Taniguchi, Masahiko Yano, Toshimasa Tsujinaka, Atsuhiro Ogawa, Shunji Morita, Katsuhiko Kaneko, Yosuke Akiyama, Hirofumi Miki, Morito Monden. Parenteral nutrition decreases hepatic dihydropyrimidine dehydrogenase activity and modulates catabolism of 5-fluorouracil in rats. In vivo (Athens, Greece). 2003 May; 17(3):219-23. doi: . [PMID: 12929570]
  • Shinichi Ikemoto, Kazunobu Sugimura, Naomasa Yoshida, Katsuyuki Kuratsukuri, Seiji Wada, Tatsuya Nakatani. Comparative antitumor activity of 5-fluorouracil and 5'-deoxy-5-fluorouridine in combination with interferon gamma in renal cell carcinoma cell lines. Anticancer research. 2002 Nov; 22(6C):4023-7. doi: . [PMID: 12553027]
  • Clasina L van der Wilt, Kees Smid, Godefridus J Peters. Effects of antifolates on the binding of 5-fluoro-2'-deoxyuridine monophosphate to thymidylate synthase. Biochemical pharmacology. 2002 Aug; 64(4):669-75. doi: 10.1016/s0006-2952(02)01219-4. [PMID: 12167486]
  • Y Mizutani, H Nakanishi, O Yoshida, M Fukushima, B Bonavida, T Miki. Potentiation of the sensitivity of renal cell carcinoma cells to TRAIL-mediated apoptosis by subtoxic concentrations of 5-fluorouracil. European journal of cancer (Oxford, England : 1990). 2002 Jan; 38(1):167-76. doi: 10.1016/s0959-8049(01)00339-2. [PMID: 11750847]
  • A Procházková, S Liu, H Friess, S Aebi, W Thormann. Determination of 5-fluorouracil and 5-fluoro-2'-deoxyuridine-5'-monophosphate in pancreatic cancer cell line and other biological materials using capillary electrophoresis. Journal of chromatography. A. 2001 May; 916(1-2):215-24. doi: 10.1016/s0021-9673(00)01171-7. [PMID: 11382294]
  • J Kralovánszky, C Katona, A Jeney, E Pandi, P Noordhuis, V Erdélyi-Tóth, L Otvös, P Kovács, C L Van der Wilt, G J Peters. 5-ethyl-2'-deoxyuridine, a modulator of both antitumour action and pharmacokinetics of 5-fluorouracil. Journal of cancer research and clinical oncology. 1999 Dec; 125(12):675-84. doi: 10.1007/s004320050333. [PMID: 10592100]
  • T W Abraham, T I Kalman, E J McIntee, C R Wagner. Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity. Journal of medicinal chemistry. 1996 Nov; 39(23):4569-75. doi: 10.1021/jm9603680. [PMID: 8917645]
  • W R Wrightson, S R Myers, S Galandiuk. HPLC analysis of 5-FU and FdUMP in tissue and serum. Biochemical and biophysical research communications. 1995 Nov; 216(3):808-13. doi: 10.1006/bbrc.1995.2693. [PMID: 7488197]
  • D Farquhar, R Chen, S Khan. 5'-[4-(Pivaloyloxy)-1,3,2-dioxaphosphorinan-2-yl]-2'-deoxy-5-fluorouridine: a membrane-permeating prodrug of 5-fluoro-2'-deoxyuridylic acid (FdUMP). Journal of medicinal chemistry. 1995 Feb; 38(3):488-95. doi: 10.1021/jm00003a012. [PMID: 7853342]
  • D Farquhar, S Khan, D N Srivastva, P P Saunders. Synthesis and antitumor evaluation of bis[(pivaloyloxy)methyl] 2'-deoxy-5-fluorouridine 5'-monophosphate (FdUMP): a strategy to introduce nucleotides into cells. Journal of medicinal chemistry. 1994 Nov; 37(23):3902-9. doi: 10.1021/jm00049a009. [PMID: 7966151]
  • T Taguchi, H Furue, H Niitani, K Ohta, S Tsukagoshi, A Wakui, K Hasegawa, I Nakao, Y Ohashi, T Tominaga. [Phase I clinical study of TT-62. Research group of TT-62]. Gan to kagaku ryoho. Cancer & chemotherapy. 1993 Feb; 20(2):241-6. doi: . [PMID: 8434962]
  • G J Peters, J Lankelma, R M Kok, P Noordhuis, C J van Groeningen, C L van der Wilt, S Meyer, H M Pinedo. Prolonged retention of high concentrations of 5-fluorouracil in human and murine tumors as compared with plasma. Cancer chemotherapy and pharmacology. 1993; 31(4):269-76. doi: 10.1007/bf00685670. [PMID: 8422689]
  • M Barberi-Heyob, J L Merlin, B Webér. Determination of 5-fluorouracil and its main metabolites in plasma by high-performance liquid chromatography. Journal of chromatography. 1992 Jan; 573(2):247-52. doi: 10.1016/0378-4347(92)80125-a. [PMID: 1534812]
  • D G Priest, M A Bunni, L R Romero-Fredes, J C Schmitz, J M Whiteley. A sensitive radioenzymatic assay for (S)-5-formyltetrahydrofolate. Analytical biochemistry. 1991 Aug; 196(2):284-9. doi: 10.1016/0003-2697(91)90467-8. [PMID: 1776677]
  • S Miyata, H Mikami, M Tai, T Hori, H Fujita. Competitive binding radioassay for the determination of 5-fluorodeoxyuridine and 5-fluorodeoxyuridine-5'-monophosphate levels in plasma and tumor tissue. Japanese journal of cancer research : Gann. 1991 Jun; 82(6):742-6. doi: 10.1111/j.1349-7006.1991.tb01911.x. [PMID: 1830300]
  • M Uchida, N Brown, D H Ho. Enzymatic conversion of 5-fluoro-2'-deoxyuridine to 5-fluorouracil or 5-fluoro-2'-deoxyuridine 5'-monophosphate in human tissues. Anticancer research. 1990 May; 10(3):779-83. doi: . [PMID: 2142396]
  • J Béres, W G Bentrude, A Kálmán, L Párkányi, J Balzarini, E De Clercq. Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates. Journal of medicinal chemistry. 1986 Apr; 29(4):488-93. doi: 10.1021/jm00154a011. [PMID: 3007759]
  • P M Pitha, V E Vengris, F H Reynolds. The role of cell membrane in the antiviral effect of interferon. Journal of supramolecular structure. 1976; 4(4):467-73. doi: 10.1002/jss.400040405. [PMID: 778494]
  • B Janik, R G Sommer. Effect of polyamines on the uptake of poly (2'-fluoro-2'-deoxyuridylic acid) by a mammalian cell line. Journal of supramolecular structure. 1976; 4(4):475-80. doi: 10.1002/jss.400040406. [PMID: 933536]