Structure via PubChem · Public domain (PubChem)
deoxycytidine
Sign in to saveAlso known as 2'-Deoxycytidine, Deoxyribose cytidine, dCYD, dC, 1-(2-deoxy-.beta.-d-ribofuranosyl)cytosine, 4-amino-1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-2(1h)-pyrimidinone
Deoxycytidine is a deoxyribonucleoside, a component of deoxyribonucleic acid. It is similar to the ribonucleoside cytidine, but with one hydroxyl group removed from the C2' position. Deoxycytidine can be phosphorylated at C5' of the deoxyribose by deoxycytidine kinase, converting it to deoxycytidine monophosphate (dCMP), a DNA precursor. dCMP can be converted to dUMP and dTMP.
Chemical data
- Formula
- C9H13N3O4
- Molecular weight
- 227.22 g/mol
- IUPAC name
- 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)O
- InChIKey
- CKTSBUTUHBMZGZ-SHYZEUOFSA-N
- XLogP
- -1.8
- Polar surface area
- 108 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
39,682 papers- Quantification of 5-methyl-2'-deoxycytidine in the DNA.Acta biochimica Polonica · 2015
- N,N-dimethyl-5-methoxymethyl-2'-deoxycytidine.Acta crystallographica. Section C, Crystal structure communications · 1999
- Human DNA replication initiation sites are specified epigenetically by oxidation of 5-methyl-deoxycytidine.Nucleic acids research · 2025
- Capecitabine.Drugs · 1999
- Deoxycytidine production by a metabolically engineered Escherichia coli strain.Microbial cell factories · 2015
via PubMed
Wikidata facts
- Has part
- oxygen
- Mass
- 227.090605896
Show 6 more facts
- found in taxon
- Escherichia coli
- chemical formula
- C₉H₁₃N₃O₄
- isomeric SMILES
- c1cn(c(=O)nc1N)[C@H]2C[C@@H]([C@H](O2)CO)O
- canonical SMILES
- N=C1N=C(O)N(C=C1)C2OC(CO)C(O)C2
- Commons category
- Deoxycytidine
- subject has role
- primary metabolite
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Clinical significance
- References
- External links
Deoxycytidine is a deoxyribonucleoside, a component of deoxyribonucleic acid. It is similar to the ribonucleoside cytidine, but with one hydroxyl group removed from the C2' position. Deoxycytidine can be phosphorylated at C5' of the deoxyribose by deoxycytidine kinase, converting it to deoxycytidine monophosphate (dCMP), a DNA precursor. dCMP can be converted to dUMP and dTMP.
Doxecitine is the international nonproprietary name.
Excerpted from Wikipedia’s “deoxycytidine” article, available under the CC BY-SA 4.0 licence.