Record Information
Version1.0
Creation date2015-10-09 22:30:30 UTC
Update date2017-01-19 02:36:22 UTC
FoodComEx IDPC000408
FoodDB RecordFDB021809
Chemical Information
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 substrate for the salvage pathway of pyrimidine nucleotide synthesis; as precursor of the cytidine triphosphate (CTP) needed in the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) biosynthetic pathway. These variations probably reflect the species differences in cytidine deaminase, the enzyme that converts cytidine to uridine in the body. The transports of cytidine into the brain's extracellular fluid, and then into neurons and glia, are essential prerequisites for cytidine to be utilized in 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, which is 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 has been discovered with the ability to deaminate cytidines on RNA or DNA. The human apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G (APOBEC3G, or hA3G) protein, 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 contain one or two copies of a signature sequence motif unique to cytidine deaminases (CTDAs). (PMID: 16769123, 15780864, 16720547) [HMDB]. Cytidine is found in many foods, some of which are sweet potato, rocket salad (sspecies), mexican groundcherry, and cinnamon.
CAS Number65-46-3
Structure
Thumb
Synonyms
SynonymSource
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-RibofuranosylcytosineGenerator
1-b-D-Ribosyl-cytosineHMDB
1-beta-D-Ribofuranosyl-cytosineHMDB
1-beta-D-RibofuranosylcytosineChEBI
1-beta-delta-Ribofuranosyl-cytosineHMDB
1-beta-delta-RibofuranosylcytosineHMDB
1-beta-delta-Ribosyl-cytosineHMDB
1-β-D-ribofuranosylcytosineGenerator
1b-D-RibofuranosylcytosineGenerator
1beta-D-RibofuranosylcytosineChEBI
1beta-delta-RibofuranosylcytosineHMDB
1beta-RibofuranosylcytosineHMDB
1β-D-ribofuranosylcytosineGenerator
4-amino-1-b-D-RIBOFURANOSYL-2(1H)-pyrimidinoneGenerator
4-amino-1-b-D-Ribofuranosylpyrimidin-2(1H)-oneGenerator
4-amino-1-BETA-D-RIBOFURANOSYL-2(1H)-pyrimidinoneChEBI
4-amino-1-beta-D-Ribofuranosylpyrimidin-2(1H)-oneChEBI
4-amino-1-beta-delta-Ribofuranosyl-2(1H)-pyrimidinoneHMDB
4-amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-amino-1-β-D-ribofuranosylpyrimidin-2(1H)-oneGenerator
4-amino-1b-D-Ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-amino-1beta-D-Ribofuranosyl-2(1H)-pyrimidinoneChEBI
4-amino-1β-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
CydChEBI
CytidinChEBI
Cytosine ribosideChEBI
Cytosine-1b-D-ribofuranosideGenerator
Cytosine-1b-delta-ribofuranosideHMDB
Cytosine-1beta-D-ribofuranosideChEBI
Cytosine-1beta-delta-ribofuranosideHMDB
Cytosine-1β-D-ribofuranosideGenerator
ZytidinChEBI
Chemical FormulaC9H13N3O5
IUPAC name4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
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)
InChI KeyUHDGCWIWMRVCDJ-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(C(O)C1O)N1C=CC(=N)N=C1O
Average Molecular Weight243.2166
Monoisotopic Molecular Weight243.085520541
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative Parents
Substituents
  • Pyrimidine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Monosaccharide
  • Pyrimidine
  • Imidolactam
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 50 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci F964
AKSci J90237
Glentham GC1136
MetaSci HMDB0000089
Sigma-Aldrich HMDB0000089
Toronto Research Chemicals C998300