Record Information
Version1.0
Creation date2015-10-09 22:29:02 UTC
Update date2017-01-19 02:36:15 UTC
FoodComEx IDPC000172
FoodDB RecordFDB021871
Chemical Information
NameDeoxycytidine
DescriptionDeoxycytidine, also known as dC, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxycytidine is an extremely weak basic (essentially neutral) compound (based on its pKa). Deoxycytidine exists in all living species, ranging from bacteria to humans. Within humans, deoxycytidine participates in a number of enzymatic reactions. In particular, deoxycytidine can be biosynthesized from dCMP; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. In addition, deoxycytidine can be converted into dCMP through its interaction with the enzyme uridine-cytidine kinase-like 1. In humans, deoxycytidine is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, Deoxycytidine has been detected, but not quantified in, several different foods, such as common sages, greenthread tea, chinese broccoli, oil palms, and lingonberries. This could make deoxycytidine a potential biomarker for the consumption of these foods. A pyrimidine 2'-deoxyribonucleoside having cytosine as the nucleobase.
CAS Number951-77-9
Structure
Thumb
Synonyms
SynonymSource
1-(2-Deoxy-b-D-ribofuranosyl)cytosinehmdb
1-(2-deoxy-beta-D-erythro-pentofuranosyl)-Cytosinehmdb
1-(2-Deoxy-beta-D-ribofuranosyl)cytosinehmdb
1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-Cytosinehmdb
1-(2-Deoxy-beta-delta-ribofuranosyl)cytosinehmdb
2-deoxy-Cytidinehmdb
2'-Deoxycytidinehmdb
4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-2(1H)-pyrimidinonehmdb
4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2(1H)-pyrimidinonehmdb
4-Amino-1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2(1H)-pyrimidinonehmdb
4-amino-1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-oneChEBI
Cytosine deoxyribonucleosidehmdb
Cytosine deoxyribosidehmdb
dCChEBI
DCYDChEBI
deoxy-Cytidinehmdb
Deoxyribose cytidinehmdb
Desoxycytidinehmdb
Chemical FormulaC9H13N3O4
IUPAC name4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
InChI IdentifierInChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
InChI KeyCKTSBUTUHBMZGZ-SHYZEUOFSA-N
Isomeric SMILESNC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](CO)O1
Average Molecular Weight227.2172
Monoisotopic Molecular Weight227.090605919
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassPyrimidine 2'-deoxyribonucleosides
Direct ParentPyrimidine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • 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 2 g
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 J91125
AKSci K726
MetaSci HMDB0000014
Sigma-Aldrich HMDB0000014
Toronto Research Chemicals D232615