Cytidine

Cytidine
Names


IUPAC name 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
Identifiers
CAS Number	65-46-3^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17562^Y
ChEMBL	ChEMBL95606^Y
ChemSpider	5940^Y
ECHA InfoCard	100.000.555
IUPHAR/BPS	4728
KEGG	D07769^Y
MeSH	Cytidine
PubChem	6175
UNII	5CSZ8459RP^Y
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
SMILES O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
Properties
Chemical formula	C₉H₁₃N₃O₅
Molar mass	243.217
Magnetic susceptibility (χ)	-123.7·10⁻⁶ cm³/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
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 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.

There are a variety of cytidine analogues 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.

In addition to its role as a pyrimidine component of RNA, cytidine has been found to control neuronal-glial glutamate cycling, with supplementation decreasing midfrontal/cerebral glutamate/glutamine levels. As such, cytidine has generated interest as a potential glutamatergic antidepressant drug.

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Wikipedia