Structure via PubChem · Public domain (PubChem)
deoxythymidine
Sign in to saveAlso known as 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione, 2'-deoxy-5-methyluridine, 5-methyl-2'-deoxyuridine, 2'-deoxythymidine, dThd, T, 1-[(2R,4S,5R)-4-hydroxy-5-methylol-tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-quinone, 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
Thymidine (symbol dT or dThd), also known as deoxythymidine is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase. The prefix deoxy- is often left out since there are no precursors of thymine nucleotides involved in RNA synthesis.
OverviewAI-generated
Deoxythymidine is a chemical compound with the formula C₁₀H₁₄N₂O₅. Its IUPAC name is 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione. The substance has a mass of 242.09 and a weight of 242.23. It features a melting point of 188.
Chemical properties include an xlogp of -1.2 and a topological polar surface area of 99.1. The molecule contains three hydrogen bond donors and five hydrogen bond acceptors, with a charge of 0. It is identified by the MCN code 2934.99.23.
Literature references for deoxythymidine number 88340. The subject is referenced by 222 other encyclopedia articles.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C10H14N2O5
- Molecular weight
- 242.23 g/mol
- IUPAC name
- 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
- SMILES
- CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
- InChIKey
- IQFYYKKMVGJFEH-XLPZGREQSA-N
- XLogP
- -1.2
- Polar surface area
- 99.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
88,340 papers- A PHGDH inhibitor reveals coordination of serine synthesis and one-carbon unit fate.Nature chemical biology · 2016
- Evaluation of deoxythymidine-based cationic amphiphiles as antimicrobial, antibiofilm, and anti-inflammatory agents.International journal of antimicrobial agents · 2023
- Distinct Phage-Encoded Enzymes for Substitution of Deoxythymidine by Deoxyuridine in Phage Genomes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
- Synthesis of beta-L-2'-deoxythymidine (L-dT).Current protocols in nucleic acid chemistry · 2006
- Investigating the safety and efficacy of deoxycytidine/deoxythymidine in mitochondrial DNA depletion disorders: phase 2 open-label trial.Journal of neurology · 2025
via PubMed
~4 min read
Encyclopedic overview
8 sectionsContents
- Chemistry
- Function
- Clinical significance
- Medical use
- Derivatives with diagnostic or therapeutic applications
- Thymidine imbalance
- References
- External links
Thymidine (symbol dT or dThd), also known as deoxythymidine is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase. The prefix deoxy- is often left out since there are no precursors of thymine nucleotides involved in RNA synthesis.
Before the boom in thymidine use caused by the need for thymidine in the production of the antiretroviral drug azidothymidine (AZT), much of the world's thymidine production came from herring sperm. Thymidine occurs almost exclusively in DNA but it also occurs in the T-loop of tRNA.
Excerpted from Wikipedia’s “deoxythymidine” article, available under the CC BY-SA 4.0 licence.