Deoxyuridine

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H12N2O5
Molecular Weight	228.202
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N2C=CC(=O)NC2=O

InChI

InChIKey=MXHRCPNRJAMMIM-SHYZEUOFSA-N

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

HIDE SMILES / InChI

Molecular Formula	C9H12N2O5
Molecular Weight	228.202
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
5-Chlorouracil, a marker of DNA damage from hypochlorous acid during inflammation. A gas chromatography-mass spectrometry assay.	2003-08-29	12810714
Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans.	2003-08-04	12898625
Professor Tom Connors and the development of novel cancer therapies by the Phase I/II Clinical Trials Committee of Cancer Research UK.	2003-08-04	12888809
Identification of a novel human uridine phosphorylase.	2003-07-18	12849978
[Antiviral activity of some 5-arylethynyl 2'-deoxyuridine derivatives].	2003-07-09	12845804
Modified DNA bearing 5(methoxycarbonylmethyl)-2'-deoxyuridine: preparation by PCR with thermophilic DNA polymerase and postsynthetic derivatization.	2003-07-07	12851926
Photochemical cross-linking of Escherichia coli Fpg protein to DNA duplexes containing phenyl(trifluoromethyl)diazirine groups.	2003-07	12846827
Conformational structures and vibrational spectra of isolated pyrimidine nucleosides: Fourier transform infrared matrix isolation study of 2-deoxyuridine.	2003-07	12788450
Increased sensitivity to gemcitabine of P-glycoprotein and multidrug resistance-associated protein-overexpressing human cancer cell lines.	2003-06-16	12799644
DNA deamination mediates innate immunity to retroviral infection.	2003-06-13	12809610
[Effects of childhood nutrition on adult health].	2003-06-05	12783768
Immunomodulation of hepatic ischemic injury via increased Bcl-X(L) and decreased Bcl-X(S).	2003-06-01	12873434
Site-specific somatic mitochondrial DNA point mutations in patients with thymidine phosphorylase deficiency.	2003-06	12813027
Independent generation and study of 5,6-Dihydro-2'-deoxyuridin-6-yl, a member of the major family of reactive intermediates formed in DNA from the effects of gamma-radiolysis.	2003-05-30	12762726
The effects of middle cerebral artery occlusion on central nervous system apoptotic events in normal and diabetic rats.	2003-05-15	12745666
Oligonucleotide based artificial nuclease (OBAN) systems. Bulge size dependence and positioning of catalytic group in cleavage of RNA-bulges.	2003-05-07	12926273
2-[11C]thymidine positron emission tomography as an indicator of thymidylate synthase inhibition in patients treated with AG337.	2003-05-07	12734319
Oligo-2'-deoxyribonucleotides containing uracil modified at the 5-position with linkers ending with guanidinium groups.	2003-04-16	12683800
A phase I trial of ZD9331, a water-soluble, nonpolyglutamatable, thymidylate synthase inhibitor.	2003-04	12684399
Elevated plasma deoxyuridine in patients with thymidine phosphorylase deficiency.	2003-03-28	12646159
The Methanococcus jannaschii dCTP deaminase is a bifunctional deaminase and diphosphatase.	2003-03-28	12538648
DFT analysis of NMR scalar interactions across the glycosidic bond in DNA.	2003-03-26	12643728
Effect of pH and sodium chloride on the strength and selectivity of the interaction of gamma [correction for tau] -cyclodextrin with some antisense nucleosides.	2003-03-26	12623195
Synthesis of 3'- and 5'-nitrooxy pyrimidine nucleoside nitrate esters: "nitric oxide donor" agents for evaluation as anticancer and antiviral agents.	2003-03-13	12620076
Evaluation of 5-[1-(2-halo(or nitro)ethoxy-2-iodoethyl)]-2'-deoxyuridines as inhibitors of herpes simplex virus.	2003-02	12751819
Pathways of accumulation and repair of deoxyuridine residues in DNA of higher and lower organisms.	2003-02	12693959
A balanced deoxyribonucleoside mixture increased the rate of DNA incorporation of 5-[125I]Iodo-2'-deoxyuridine in glioblastoma cells.	2003-02	12667304
Non-classical antifolates, 5-(N-phenylpyrrolidin-3-yl)-2,4,6-triaminopyrimidines and 2,4-Diamino-6(5H)-oxopyrimidines, synthesis and antitumor studies.	2003-01-02	12467717
Synthesis of a novel aldehyde: 4-O-methyl-5-formylmethyl-2'-deoxyuridine.	2003	12708802
Microwave-assisted synthesis of O'-adamantylated uracil-derived nucleosides.	2003	12708798
Hydrolytic reactions of diribonucleoside 3',5'-(3'-N-phosphoramidates): kinetics and mechanisms for the P-O and P-N bond cleavage of 3'-amino-3'-deoxyuridylyl-3',5'-uridine.	2002-12-04	12452710
DNA duplexes containing photoactive derivatives of 2'-deoxyuridine as photocrosslinking probes for EcoRII DNA methyltransferase-substrate interaction.	2002-12	12437380
[4'-Thio-5-ethyl-2'-deoxyuridine 5'-phosphonates: synthesis and antiviral activity].	2002-11-01	12408030
Inhibition of the replication of a hepatitis C virus-like RNA template by interferon and 3'-deoxycytidine.	2002-11	12718408
Deoxyuridine accumulation in urine in thymidine phosphorylase deficiency (MNGIE).	2002-11	12638947
5-amino-2'-deoxyuridine, a novel thymidine analogue for high-resolution footprinting of protein-DNA complexes.	2002-10-31	12599479
Synthesis of 5-(pyridinyl and pyridiniumyl)-2'-deoxyuridine nucleosides: reversible electron traps for DNA.	2002-10	12502283
Radiolabelled thymidines and deoxyuridines for measuring cellular proliferation in tumours--an update.	2002-10	12352590
Rationale of 5-(125)I-iodo-4'-thio-2'-deoxyuridine as a potential iodinated proliferation marker.	2002-09	12215562
Formation of 2'-deoxyuridine hydrates upon exposure of nucleosides to gamma radiation and UVC-irradiation of isolated and cellular DNA.	2002-08	12659498
Chemical synthesis and biochemical properties of oligonucleotides that contain the (5'S,5S,6S)-5',6-cyclo-5-hydroxy-5,6-dihydro-2'-deoxyuridine DNA lesion.	2002-06-03	12325009
Conformation dependent DNA photoligation via sensitizer tethered 5-carboxyvinyluracil.	2002	12903152
Synthesis of 5-(2,2'-bipyridinyl and 2,2'-bipyridinediiumyl)-2'-deoxyuridine nucleosides: precursors to metallo-DNA conjugates.	2002	12484450
Prolactin signaling and Stat5: going their own separate ways?	2002	12473164
Glycine rich P-loop motif in deoxyuridine pyrophosphatase.	2001-12	12369927
X-ray analyses of DNA dodecamers containing 2'-deoxy-5-formyluridine.	2001	12836373
Template directed DNA photoligation via substituted 2'-deoxyuridine.	2001	12836326
Evidence for a Schiff base formation of peptides derived from RecA with single-stranded oligonucleotides containing 5-formyl-2'-deoxyuridine.	2001	12836321
Investigation of antisense DNA having C-5 polyamine substituted 2'-deoxyuridine derivative.	2001	12836297
Synthesis of 5-substituted [N3-15N]-pyrimidine nucleosides: Developing model systems for NMR studies of substituent effects on the N-H...N hydrogen bond in duplex DNA.	2001	12836238

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:09 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:09 GMT 2025`
Record UNII	W78I7AY22C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-23615

Preferred Name

English

Deoxyuridine

Systematic Name

English

1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)URACIL

Common Name

English

2-DEOXYURIDINE

Common Name

English

2'-DEOXYURIDINE

Systematic Name

English

DEOXYURIDINE [MI]

Common Name

English

Classification Tree Code System Code

LOINC

59193-3