Cytidine

Not to be confused with cytosine, cysteine, cystine, or cytisine.

Cytidine
IUPAC name 4-​amino-​1-​[3,​4-​dihydroxy-​5-​(hydroxymethyl)​tetrahydrofuran-​2-​yl]​pyrimidin-​2-​one
Identifiers
CAS number	65-46-3 Y
PubChem	6175
ChemSpider	5940 Y
UNII	5CSZ8459RP Y
KEGG	D07769 Y
MeSH	Cytidine
ChEBI	CHEBI:17562 Y
ChEMBL	CHEMBL95606 Y
Jmol-3D images	Image 1
SMILES O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
InChI InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1 Y Key: UHDGCWIWMRVCDJ-XVFCMESISA-N Y InChI=1/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1 Key: UHDGCWIWMRVCDJ-XVFCMESIBD
Properties
Molecular formula	C9H13N3O5
Molar mass	243.22 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cytidine is a nucleoside molecule that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N₁-glycosidic bond. Cytidine is a component of RNA.

If cytosine is attached to a deoxyribose ring, it is known as a deoxycytidine.

Dietary sources of cytidine

Dietary sources of cytidine include foods with high RNA (ribonucleic acid) content, such as organ meats, Brewer's yeast, as well as pyrimidine-rich foods such as beer. During digestion, RNA-rich foods are broken-down into ribosyl pyrimidines (cytidine and uridine), which are absorbed intact. In humans, dietary cytidine is converted into uridine, which is probably the compound behind cytidine's metabolic effects.

Cytidine analogs

There are a variety of cytidine analogs with potentially useful pharmacology. For example, KP-1461 is an anti-HIV agent that works as a viral mutagen, and zebularine exists in E. coli and is being examined for chemotherapy. Low doses of azacitidine and its analog decitabine have shown results against cancer through epigenetic demethylation.