Common NameCytidine
DescriptionCytidine is a nucleoside that is composed of the base cytosine linked to the five-carbon sugar D-ribose. Cytidine is a pyrimidine that besides being incorporated into nucleic acids, can serve as a substrate for the salvage pathway of pyrimidine nucleotide synthesis. It is a precursor of cytidine triphosphate (CTP) needed in the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) biosynthetic pathways. These variations probably reflect the species differences in cytidine deaminase, the enzyme that converts cytidine to uridine in the body. The transport of cytidine into the brain's extracellular fluid, and then into neurons and glia, are essential prerequisites for cytidine to be utilized in the brain. An efficient mechanism mediating the brain uptake of circulating cytidine has not yet been demonstrated. The biosynthesis of PC, the most abundant phosphatide in the brain, via the Kennedy pathway requires phosphocholine and cytidine triphosphate (CTP), a cytidine nucleotide involved in the rate-limiting step. The enzyme that converts CTP to endogenous CDP-choline (CTP:phosphocholine cytidylyltransferase) is unsaturated at physiological brain CTP levels. APOBEC is a family of enzymes that has been discovered with the ability to deaminate cytidines on RNA or DNA. The human apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G protein (APOBEC3G, or hA3G), provides cells with an intracellular antiretroviral activity that is associated with the hypermutation of viral DNA through cytidine deamination. Indeed, hA3G belongs to a family of vertebrate proteins that contains one or two copies of a signature sequence motif unique to cytidine deaminases (CTDAs) (PMID: 16769123 , 15780864 , 16720547 ).
Structure
Molecular FormulaC9H13N3O5
Average Mass243.21660
Monoisotopic Mass243.08552
IUPAC Name4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
Traditional NameCytidine
CAS Registry Number65-46-3
SMILESNc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
InChI IdentifierInChI=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
InChI KeyUHDGCWIWMRVCDJ-XVFCMESISA-N
CHEBI IDCHEBI:17562
HMDB IDHMDB0000089
Pathways
NameSMPDB/PathBank
Pyrimidine metabolism
Beta Ureidopropionase Deficiency
Dihydropyrimidinase Deficiency
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
UMP Synthase Deficiency (Orotic Aciduria)
StateNot Available
Water Solubility4.38e+01 g/l
logP-2.18
logS-0.74
pKa (Strongest Acidic)12.55
pKa (Strongest Basic)-0.55
Hydrogen Acceptor Count7
Hydrogen Donor Count4
Polar Surface Area128.61 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity54.54 m³·mol⁻¹
Polarizability22.39

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