<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:52 UTC</creation_date>
  <update_date>2019-11-26 03:05:39 UTC</update_date>
  <accession>FDB011882</accession>
  <name>Cytidine 5'-(dihydrogen phosphate)</name>
  <description>Isolated from biol. sources, e.g. Phaseolus aureus (mung bean) seedlings

Cytidine monophosphate is an ester of phosphoric acid with the nucleoside cytidine; it is a nucleotide found in RNA.</description>
  <synonyms>
    <synonym>5-Cytidylate</synonym>
    <synonym>5-Cytidylic acid</synonym>
    <synonym>5'-CMP</synonym>
    <synonym>5'-Cytidylic acid, 9CI, 8CI</synonym>
    <synonym>CMP</synonym>
    <synonym>Cytidine 5'-ate</synonym>
    <synonym>Cytidine 5'-monoate</synonym>
    <synonym>Cytidine 5'-monoic acid</synonym>
    <synonym>Cytidine 5'-monoorate</synonym>
    <synonym>Cytidine 5'-monooric acid</synonym>
    <synonym>Cytidine 5'-monophosphate</synonym>
    <synonym>Cytidine 5'-monophosphorate</synonym>
    <synonym>Cytidine 5'-monophosphoric acid</synonym>
    <synonym>Cytidine 5'-orate</synonym>
    <synonym>Cytidine 5'-oric acid</synonym>
    <synonym>Cytidine 5'-phosphate</synonym>
    <synonym>Cytidine 5'-phosphorate</synonym>
    <synonym>Cytidine 5'-phosphoric acid</synonym>
    <synonym>Cytidine mono(dihydrogen ate)</synonym>
    <synonym>Cytidine monoate</synonym>
    <synonym>Cytidine monophosphate</synonym>
    <synonym>Cytidine-5'-monoate</synonym>
    <synonym>Cytidine-5'-monoic acid</synonym>
    <synonym>Cytidylate</synonym>
    <synonym>Cytidylic acid</synonym>
    <synonym>pC</synonym>
  </synonyms>
  <chemical_formula>C9H14N3O8P</chemical_formula>
  <average_molecular_weight>323.1965</average_molecular_weight>
  <monisotopic_moleculate_weight>323.051850951</monisotopic_moleculate_weight>
  <iupac_name>{[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>63-37-6</cas_registry_number>
  <smiles>OC1C(O)C(OC1COP(O)(O)=O)N1C=CC(=N)N=C1O</smiles>
  <inchi>InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)</inchi>
  <inchikey>IERHLVCPSMICTF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group  linked to the ribose moiety.</description>
    <direct_parent>Pyrimidine ribonucleoside monophosphates</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <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>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</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>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</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>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.89e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 233 dec. (monohydrate)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>2.57</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>{[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>323.1965</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>323.051850951</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1C(O)C(OC1COP(O)(O)=O)N1C=CC(=N)N=C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H14N3O8P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>IERHLVCPSMICTF-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>176.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>76.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>27.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>10</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP00463</smpdb_id>
      <kegg_map_id>map00562</kegg_map_id>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP00479</smpdb_id>
      <kegg_map_id></kegg_map_id>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP00046</smpdb_id>
      <kegg_map_id>map00240</kegg_map_id>
    </pathway>
    <pathway>
      <name>Transcription/Translation</name>
      <smpdb_id>SMP00019</smpdb_id>
      <kegg_map_id></kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>81317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>121143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>805029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>181520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391689</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00095</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id>C</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce2ed48328&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed48120&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed43da0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed43940&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed43648&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed43350&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed42770&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed41cd0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed41a00&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ed41488&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>26.225</average_value>
      <max_value>49.55</max_value>
      <min_value>2.9</min_value>
      <unit>uM</unit>
    </food>
    <food>
      <name>Pulses</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Alpha-N-acetyl-neuraminyl-2,3-beta-galactosyl-1,3-N-acetyl-galactosaminide alpha-2,6-sialyltransferase</name>
      <uniprot_id>Q9H4F1</uniprot_id>
      <uniprot_name/>
      <gene_name>ST6GALNAC4</gene_name>
    </enzyme>
    <enzyme>
      <name>Alpha-N-acetylneuraminide alpha-2,8-sialyltransferase</name>
      <uniprot_id>Q92185</uniprot_id>
      <uniprot_name/>
      <gene_name>ST8SIA1</gene_name>
    </enzyme>
    <enzyme>
      <name>CMP-N-acetylneuraminate-beta-1,4-galactoside alpha-2,3-sialyltransferase</name>
      <uniprot_id>Q11203</uniprot_id>
      <uniprot_name/>
      <gene_name>ST3GAL3</gene_name>
    </enzyme>
    <enzyme>
      <name>CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1</name>
      <uniprot_id>Q11201</uniprot_id>
      <uniprot_name/>
      <gene_name>ST3GAL1</gene_name>
    </enzyme>
    <enzyme>
      <name>CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 4</name>
      <uniprot_id>Q11206</uniprot_id>
      <uniprot_name/>
      <gene_name>ST3GAL4</gene_name>
    </enzyme>
    <enzyme>
      <name>Cytosolic 5'-nucleotidase 3</name>
      <uniprot_id>Q9H0P0</uniprot_id>
      <uniprot_name/>
      <gene_name>NT5C3</gene_name>
    </enzyme>
    <enzyme>
      <name>Lactosylceramide alpha-2,3-sialyltransferase</name>
      <uniprot_id>Q9UNP4</uniprot_id>
      <uniprot_name/>
      <gene_name>ST3GAL5</gene_name>
    </enzyme>
    <enzyme>
      <name>N-acylneuraminate cytidylyltransferase</name>
      <uniprot_id>Q8NFW8</uniprot_id>
      <uniprot_name/>
      <gene_name>CMAS</gene_name>
    </enzyme>
    <enzyme>
      <name>Phosphatidylcholine:ceramide cholinephosphotransferase 1</name>
      <uniprot_id>Q86VZ5</uniprot_id>
      <uniprot_name/>
      <gene_name>SGMS1</gene_name>
    </enzyme>
    <enzyme>
      <name>Phosphatidylcholine:ceramide cholinephosphotransferase 2</name>
      <uniprot_id>Q8NHU3</uniprot_id>
      <uniprot_name/>
      <gene_name>SGMS2</gene_name>
    </enzyme>
    <enzyme>
      <name>Phosphopantothenate--cysteine ligase</name>
      <uniprot_id>Q9HAB8</uniprot_id>
      <uniprot_name/>
      <gene_name>PPCS</gene_name>
    </enzyme>
    <enzyme>
      <name>Type 2 lactosamine alpha-2,3-sialyltransferase</name>
      <uniprot_id>Q9Y274</uniprot_id>
      <uniprot_name/>
      <gene_name>ST3GAL6</gene_name>
    </enzyme>
    <enzyme>
      <name>UMP-CMP kinase 2, mitochondrial</name>
      <uniprot_id>Q5EBM0</uniprot_id>
      <uniprot_name/>
      <gene_name>CMPK2</gene_name>
    </enzyme>
    <enzyme>
      <name>Uridine-cytidine kinase-like 1</name>
      <uniprot_id>Q9NWZ5</uniprot_id>
      <uniprot_name/>
      <gene_name>UCKL1</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
