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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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,^[1] 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.^[1] In humans, dietary cytidine is converted into uridine,^[2] which is probably the compound behind cytidine's metabolic effects.

Cytidine analogues

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,^[3] 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.^[4]

Biological actions

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.^[5] As such, cytidine has generated interest as a potential glutamatergic antidepressant drug.^[5]

References

External links

• Cytidine MS Spectrum