<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:52 UTC</creation_date>
  <update_date>2025-11-18 22:29:06 UTC</update_date>
  <accession>FDB001213</accession>
  <name>Acadesine 5'-monophosphate</name>
  <description>Produced by the action of brewer's yeast on the riboside. The 5'-phosphate and its nontoxic salts are potent flavour enhancers of soups, canned foods, beverages, etc [DFC]. Acadesine 5'-monophosphate is found in herbs and spices.</description>
  <synonyms>
    <synonym>1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide</synonym>
    <synonym>5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide</synonym>
    <synonym>5-Amino-1-(5'-phosphofuranoribosyl)-4-imidazolecarboxamide</synonym>
    <synonym>5-Aminoimidazole-4-carboxamide ribotide</synonym>
    <synonym>5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole</synonym>
    <synonym>5'-P-ribosyl-5-amino-4-imidazole carboxamide</synonym>
    <synonym>5'-Phospho-b-D-ribosyl-5-amino-4-imidazolecarboxamide</synonym>
    <synonym>5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide</synonym>
    <synonym>5'-Phosphoribosyl-5-amino-4-imidazole carboxamide</synonym>
    <synonym>5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide</synonym>
    <synonym>Acadesine 5'-monophosphate</synonym>
    <synonym>AICA ribonucleotide</synonym>
    <synonym>AICA riboside 5'-monophosphate</synonym>
    <synonym>AICA ribotide</synonym>
    <synonym>AICAR</synonym>
    <synonym>Aminoimidazole carboxamide ribonucleotide</synonym>
    <synonym>ZMP</synonym>
  </synonyms>
  <chemical_formula>C9H15N4O8P</chemical_formula>
  <average_molecular_weight>338.2112</average_molecular_weight>
  <monisotopic_moleculate_weight>338.062749988</monisotopic_moleculate_weight>
  <iupac_name>5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazole-4-carboximidic acid</iupac_name>
  <traditional_iupac>5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazole-4-carboximidic acid</traditional_iupac>
  <cas_registry_number>3031-94-5</cas_registry_number>
  <smiles>NC1=C(N=CN1C1OC(COP(O)(O)=O)C(O)C1O)C(O)=N</smiles>
  <inchi>InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)</inchi>
  <inchikey>NOTGFIUVDGNKRI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.</description>
    <direct_parent>1-ribosyl-imidazolecarboxamides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Imidazole ribonucleosides and ribonucleotides</class>
    <sub_class>1-ribosyl-imidazolecarboxamides</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>2-heteroaryl carboxamides</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aminoimidazoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonylimidazoles</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</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>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-ribosyl-imidazolecarboxamide</substituent>
      <substituent>2-heteroaryl carboxamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminoimidazole</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazole-4-carbonyl group</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</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>Primary carboxylic acid amide</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.74e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-4.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>6.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazole-4-carboximidic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>338.2112</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>338.062749988</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NC1=C(N=CN1C1OC(COP(O)(O)=O)C(O)C1O)C(O)=N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H15N4O8P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>NOTGFIUVDGNKRI-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>204.37</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>80.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>28.93</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>10</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119109</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
      <spectrum_id>3413980</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2396</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>122041</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <spectrum_id>207211</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>207212</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>207213</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>207214</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>207215</spectrum_id>
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      <spectrum_id>207216</spectrum_id>
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      <spectrum_id>207218</spectrum_id>
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      <spectrum_id>207219</spectrum_id>
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      <spectrum_id>207220</spectrum_id>
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      <spectrum_id>207224</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>207225</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>207226</spectrum_id>
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  </spectra>
  <hmdb_id>HMDB01517</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>18406</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
