<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:09:44 UTC</creation_date>
  <update_date>2026-05-14 17:27:09 UTC</update_date>
  <accession/>
  <common_name>Cytidine</common_name>
  <class>SmallMolecule</class>
  <description>Cytidine belongs to the pyrimidine nucleosides, a class of nucleosides, nucleotides, and analogues within the organic compounds. It has the chemical formula C9H13N3O5 and an average molecular weight of 243.22 g/mol.

In industrial applications, the compound is utilized as a humectant, as well as a softener and conditioner. Cytidine is found in or released from 16 recorded sources across several categories. Within food, food processing and cookware, it is associated with fermentation processes for beer, the preparation of malt, wort, and wine or sparkling wine, and food preservation. In the sector of electrical and electronic equipment, it is linked to electrodes, hybrid capacitors, electric switches, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Additionally, it is found in household cleaning and consumer products, including soap detergents, tobacco smoke filters, cigar cigarettes, pipe accessories, and other smoking requisites. Regarding its biological activity, cytidine has one recorded protein target, which is uridine-cytidine kinase 2 (UCK2).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C9H13N3O5</chemical_formula>
  <average_molecular_weight>243.2166</average_molecular_weight>
  <monisotopic_moleculate_weight>243.085520541</monisotopic_moleculate_weight>
  <iupac_name>4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</iupac_name>
  <traditional_iupac>cytarabine</traditional_iupac>
  <cas_registry_number>65-46-3</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O</smiles>
  <inchi>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>
  <inchikey>UHDGCWIWMRVCDJ-XVFCMESISA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class/>
    <direct_parent>Pyrimidine nucleosides</direct_parent>
    <alternate_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>beta-D-arabinoside</descriptor>
      <descriptor>monosaccharide derivative</descriptor>
      <descriptor>pyrimidine nucleoside</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0000046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Ureidopropionase Deficiency</name>
      <smpdb_id>SMP0000172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>UMP Synthase Deficiency (Orotic Aciduria)</name>
      <smpdb_id>SMP0000219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydropyrimidinase Deficiency</name>
      <smpdb_id>SMP0000178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)</name>
      <smpdb_id>SMP0000202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Ureidopropionase Deficiency</name>
      <smpdb_id>SMP0125716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>UMP Synthase Deficiency (Orotic Aciduria)</name>
      <smpdb_id>SMP0125717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydropyrimidinase Deficiency</name>
      <smpdb_id>SMP0125719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)</name>
      <smpdb_id>SMP0125720</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.38e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.062</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>243.2166</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>243.085520541</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N3O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UHDGCWIWMRVCDJ-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>128.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
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  <metabolism/>
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  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bcf81f468&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB02097</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6175</pubchem_compound_id>
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  <biocyc_id/>
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  <actor_id/>
  <pdb_id/>
  <wikipidia/>
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</compound>
