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Record Information
Version1.0
Creation Date2016-09-30 22:18:27 UTC
Update Date2020-05-21 16:27:11 UTC
BMDB IDBMDB0000014
Secondary Accession Numbers
  • BMDB00014
Metabolite Identification
Common NameDeoxycytidine
Description2'-Deoxycytidine, 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. 2'-Deoxycytidine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 2'-Deoxycytidine exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-oneChEBI
dCChEBI
DCYDChEBI
2'-DeoxycytidineKegg
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
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
Cytosine deoxyribonucleosideHMDB
Cytosine deoxyribosideHMDB
Deoxy-cytidineHMDB
Deoxyribose cytidineHMDB
DesoxycytidineHMDB
Deoxyribonucleoside, cytosineHMDB
Deoxyriboside, cytosineHMDB
DeoxycytidineChEBI
Chemical FormulaC9H13N3O4
Average Molecular Weight227.2172
Monoisotopic Molecular Weight227.090605919
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number951-77-9
SMILESNot Available
InChI Identifier
InChI=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
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point207 - 210 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility870 mg/mLNot Available
LogP-1.77HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • All Tissues
  • Liver
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000014
DrugBank IDDB02594
Phenol Explorer Compound IDNot Available
FooDB IDFDB021871
KNApSAcK IDNot Available
Chemspider ID13117
KEGG Compound IDC00881
BioCyc IDDEOXYCYTIDINE
BiGG ID36280
Wikipedia LinkDeoxycytidine
METLIN ID3367
PubChem Compound13711
PDB IDNot Available
ChEBI ID15698
References
Synthesis ReferenceFox, Jack F.; Yung, Naishun; Wempen, Iris; Hoffer, Max. Pyrimidine nucleosides. XII. Direct synthesis of 2'-deoxycytidine and its a-anomer. Journal of the American Chemical Society (1961), 83 4066-50.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Enzymes

General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
O46411
Molecular weight:
64841.0
Reactions
dCMP + Water → Deoxycytidine + Hydrogen phosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor (By similarity).
Gene Name:
UCK1
Uniprot ID:
Q0P5A4
Molecular weight:
31195.0
Reactions
Deoxycytidine + Adenosine triphosphate → dCMP + ADPdetails
General function:
Nucleotide transport and metabolism
Specific function:
Phosphorylates the deoxyribonucleosides deoxycytidine, deoxyguanosine and deoxyadenosine.
Gene Name:
DCK
Uniprot ID:
Q3MHR2
Molecular weight:
30329.0