Deoxyuridine
2-Deoxyuridine is a naturally occurring nucleoside. It is similar in chemical structure to uridine, but without the 2-hydroxyl group. It is considered to be an antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemia due to vitamin B12 and folate deficiencies.
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB00012 (Deoxyuridine)
C9H12N2O5
228.202
228.074621504
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
2-deoxyuridine
951-78-0
OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O
InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
MXHRCPNRJAMMIM-SHYZEUOFSA-N
This compound belongs to the class of chemical entities known as pyrimidine 2-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
Chemical entities
Organic compounds
Nucleosides, nucleotides, and analogues
Pyrimidine nucleosides
Pyrimidine 2-deoxyribonucleosides
Aromatic heteromonocyclic compounds
Detected and Quantified
Not Available
Solid
GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0900000000-c680f47a48626bc1de41View in MoNA
GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0900000000-13135426d5efdf47090cView in MoNA
GC-MS Spectrum – GC-MS (3 TMS)splash10-0v4i-2910000000-b0c82cef369c86d585bcView in MoNA
GC-MS Spectrum – GC-MS (3 TMS)splash10-0udi-2900000000-c2cdba9e46defe05a225View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-03di-1900000000-6610506190427bbb3b6cView in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9800000000-af237f79161aa13a5893View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-022d-9100000000-a06cdd7ea870d049c8a9View in MoNA
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-001i-0910000000-8cef8299b80deeefe1aeView in MoNA
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-001i-0900000000-043d88b7ac473889f319View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Normal
Eosinophilic esophagitis
None
None
Not Available
Not Available
Not Available
Not Available
FDB021870
Not Available
13118
C00526
DEOXYURIDINE
35251
Deoxyuridine
HMDB00012
HMDB00012
5086
13712
DUR
16450
- Li KM, Rivory LP, Clarke SJ: Rapid quantitation of plasma 2-deoxyuridine by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry and its application to pharmacodynamic studies in cancer patients. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):121-30. Epub 2005 Apr 19. [PubMed:15866500 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Di Stefano G, Busi C, Derenzini M, Trere D, Fiume L: Conjugation of 5-fluoro-2-deoxyuridine with lactosaminated poly-l-lysine to reduce extrahepatic toxicity in the treatment of hepatocarcinomas. Ital J Gastroenterol Hepatol. 1998 Apr;30(2):173-7. [PubMed:9675653 ]
- Reidy JA: Deoxyuridine increases folate-sensitive fragile site expression in human lymphocytes. Am J Med Genet. 1987 Jan;26(1):1-5. [PubMed:3812550 ]
- Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
- Huong PL, Kolk AH, Eggelte TA, Verstijnen CP, Gilis H, Hendriks JT: Measurement of antigen specific lymphocyte proliferation using 5-bromo-deoxyuridine incorporation. An easy and low cost alternative to radioactive thymidine incorporation. J Immunol Methods. 1991 Jul 5;140(2):243-8. [PubMed:1906076 ]
- Kanazawa S, Herbert V: Detection of folate deficiency in alcoholism using the peripheral blood lymphocyte deoxyuridine suppression test. J Nutr Sci Vitaminol (Tokyo). 1986 Jun;32(3):251-7. [PubMed:3761048 ]
- Zittoun J, Zittoun R: Modern clinical testing strategies in cobalamin and folate deficiency. Semin Hematol. 1999 Jan;36(1):35-46. [PubMed:9930567 ]
- Fairbanks LD, Marinaki AM, Carrey EA, Hammans SR, Duley JA: Deoxyuridine accumulation in urine in thymidine phosphorylase deficiency (MNGIE). J Inherit Metab Dis. 2002 Nov;25(7):603-4. [PubMed:12638947 ]
- Remacha A, Barcelo MJ, Pastor M, Ubeda J, Espadaler M, Gimferrer E: The deoxyuridine suppression test in peripheral lymphocytes. Eur J Haematol. 1990 Mar;44(3):196-200. [PubMed:2328792 ]
- Galanis E, Goldberg R, Reid J, Atherton P, Sloan J, Pitot H, Rubin J, Adjei AA, Burch P, Safgren SL, Witzig TE, Ames MM, Erlichman C: Phase I trial of sequential administration of raltitrexed (Tomudex) and 5-iodo-2-deoxyuridine (IdUrd). Ann Oncol. 2001 May;12(5):701-7. [PubMed:11432631 ]
- (). Akhrem, A.A. et al., Org. Magn. Reson., 1979, 12, 247, (cmr). .
- (). Fox, J.J. et al., Adv. Carbohydr. Chem., 1959, 14, 283, (rev). .
- (). Rimerman, R.A. et al., J. Chromatogr., B: Biomed. Appl., 1993, 619, 29-35, (5'-triphosphate). .
- (). Schinazi, R.F. et al., J. Med. Chem., 1978, 21, 1141, (synth, acid). .
- (). Barr, P.J. et al., Tetrahedron, 1980, 36, 1269, (cryst struct). .
- (). Ludwig, J. et al., Synthesis, 1982, 32-34, (5'-phosphate). .
- (). Dematte, N. et al., Comp. Biochem. Physiol., B: Comp. Biochem., 1986, 84, 11, (isol, acid). .
- (). Rahman, A. et al., Acta Cryst. B, 1972, 28, 2260, (cryst struct). .
- (). Sakema, S. et al., Comp. Biochem. Physiol., B: Comp. Biochem., 1985, 82, 107-109, (isol). .
- (). Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 816A, (ir). .
- (). Kikugawa, K. et al., Chem. Pharm. Bull., 1969, 17, 785, (synth, deriv). .
- (). Sprecher, C.A. et al., Biopolymers, 1977, 16, 2243, (cd). .
- (). Komori, T. et al., Annalen, 1980, 653-668, (isol). .
- (). Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 374B, (nmr). .
- (). Hruska, F.E. et al., Can. J. Chem., 1974, 52, 497, (conformn, pmr). .
- (). U.S. Pat., 1966, 3 280 104, CA, 66, 38207y. .
- (). Lidgren, G. et al., J. Nat. Prod., 1988, 51, 1277-1280, (2'-Deoxy-3-methyluridine). .
Enzymes
- General function:
- Involved in zinc ion binding
- Specific function:
- Not Available
- Gene Name:
- AID
- Uniprot ID:
- Q546Y9
- Molecular weight:
- 23953.3
- General function:
- Involved in purine-nucleoside phosphorylase activity
- Specific function:
- The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
- Gene Name:
- PNP
- Uniprot ID:
- P00491
- Molecular weight:
- 32117.69
Reactions
- General function:
- Involved in ATP binding
- Specific function:
- Deoxyribonucleoside kinase that phosphorylates thymidine, deoxycytidine, and deoxyuridine. Also phosphorylates anti-viral and anti-cancer nucleoside analogs.
- Gene Name:
- TK2
- Uniprot ID:
- O00142
- Molecular weight:
- 27561.495
Reactions
- General function:
- Involved in transferase activity, transferring glycosyl groups
- Specific function:
- May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro.Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
- Gene Name:
- TYMP
- Uniprot ID:
- P19971
- Molecular weight:
- 49954.965
Reactions
- General function:
- Involved in ATP binding
- Specific function:
- May contribute to UTP accumulation needed for blast transformation and proliferation.
- Gene Name:
- UCKL1
- Uniprot ID:
- Q9NWZ5
- Molecular weight:
- 59465.77
- General function:
- Involved in ATP binding
- Specific function:
- Not Available
- Gene Name:
- Not Available
- Uniprot ID:
- Q8IZR3
- Molecular weight:
- 35439.6
- General function:
- Not Available
- Specific function:
- DNA deaminase (cytidine deaminase) that mediates a form of innate resistance to retroviral infections (at least to HIV-1 infection) by triggering G-to-A hypermutation in the newly synthesized viral DNA. The replacements C-to-U in the minus strand DNA of HIV-1 during reverse transcription, leads to G-to-A transitions in the plus strand. The inhibition of viral replication is either due to the degradation of the minus strand before its integration or to the lethality of the hypermutations. Modification of both DNA strands is not excluded. This antiviral activity is neutralized by the virion infectivity factor (VIF), that prevents the incorporation of APOBEC3G into progeny HIV-1 virions by both inhibiting its translation and/or by inducing its ubiquitination and subsequent degradation by the 26S proteasome. May also prevent the transposition of a subset of retroelements. Binds a variety of RNAs, but does not display detectable APOB, NF1 and NAT1 mRNA editing.
- Gene Name:
- APOBEC3G
- Uniprot ID:
- Q9HC16
- Molecular weight:
- 11822.52