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.
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
Wikidata facts
- Mass
- 242.09
Show 6 more facts
- MCN code
- 2934.99.23
- chemical formula
- C₁₀H₁₄N₂O₅
- canonical SMILES
- CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
- Commons category
- Deoxythymidine
- isomeric SMILES
- CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
- melting point
- 188
via Wikidata · CC0
~4 min read
Article
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.