Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:27:33 UTC
Update Date2022-08-30 23:03:53 UTC
MiMeDB IDMMDBc0000023
Metabolite Identification
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
Synonyms
ValueSource
1-beta-D-RibofuranosylcytosineChEBI
1beta-D-RibofuranosylcytosineChEBI
4-AMINO-1-BETA-D-ribofuranosyl-2(1H)-pyrimidinoneChEBI
4-Amino-1-beta-D-ribofuranosylpyrimidin-2(1H)-oneChEBI
4-Amino-1beta-D-ribofuranosyl-2(1H)-pyrimidinoneChEBI
CydChEBI
CytidinChEBI
Cytosine ribosideChEBI
Cytosine-1beta-D-ribofuranosideChEBI
ZytidinChEBI
PosilentKegg
1-b-D-RibofuranosylcytosineGenerator
1-Β-D-ribofuranosylcytosineGenerator
1b-D-RibofuranosylcytosineGenerator
1Β-D-ribofuranosylcytosineGenerator
4-AMINO-1-b-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-AMINO-1-β-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-Amino-1-b-D-ribofuranosylpyrimidin-2(1H)-oneGenerator
4-Amino-1-β-D-ribofuranosylpyrimidin-2(1H)-oneGenerator
4-Amino-1b-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-Amino-1β-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
Cytosine-1b-D-ribofuranosideGenerator
Cytosine-1β-D-ribofuranosideGenerator
1-(b-D-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
1-(b-delta-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
1-b-D-Ribosyl-cytosineHMDB
1-beta-D-Ribofuranosyl-cytosineHMDB
1-beta-delta-Ribofuranosyl-cytosineHMDB
1-beta-delta-RibofuranosylcytosineHMDB
1-beta-delta-Ribosyl-cytosineHMDB
1beta-delta-RibofuranosylcytosineHMDB
1beta-RibofuranosylcytosineHMDB
4-Amino-1-beta-delta-ribofuranosyl-2(1H)-pyrimidinoneHMDB
Cytosine-1b-delta-ribofuranosideHMDB
Cytosine-1beta-delta-ribofuranosideHMDB
Cytosine ribonucleosideHMDB
Ribonucleoside, cytosineHMDB
Riboside, cytosineHMDB
1-(beta-D-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
1-(Β-D-ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
Chemical FormulaC9H13N3O5
Average Molecular Weight243.2166
Monoisotopic Molecular Weight243.085520541
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
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI Identifier
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
InChI KeyUHDGCWIWMRVCDJ-XVFCMESISA-N