<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-03-17 23:26:11 UTC</creation_date>
  <update_date>2025-11-19 02:38:58 UTC</update_date>
  <accession>FDB021670</accession>
  <name>(E)-Zeatin glucoside</name>
  <description>(e)-zeatin glucoside is a member of the class of compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol (e)-zeatin glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (e)-zeatin glucoside can be found in soy bean, which makes (e)-zeatin glucoside a potential biomarker for the consumption of this food product.</description>
  <synonyms>
    <synonym>(E)-Zeatin glucoside</synonym>
    <synonym>(E)-Zeatin O-b-D-glucopyranoside</synonym>
    <synonym>tran-Zeatin glucoside</synonym>
  </synonyms>
  <chemical_formula>C16H23N5O6</chemical_formula>
  <average_molecular_weight>381.3837</average_molecular_weight>
  <monisotopic_moleculate_weight>381.164833493</monisotopic_moleculate_weight>
  <iupac_name>2-(hydroxymethyl)-6-{[(2E)-2-methyl-4-[(9H-purin-6-yl)amino]but-2-en-1-yl]oxy}oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>2-(hydroxymethyl)-6-{[(2E)-2-methyl-4-(9H-purin-6-ylamino)but-2-en-1-yl]oxy}oxane-3,4,5-triol</traditional_iupac>
  <cas_registry_number>56329-06-7</cas_registry_number>
  <smiles>C\C(COC1OC(CO)C(O)C(O)C1O)=C/CNC1=NC=NC2=C1N=CN2</smiles>
  <inchi>InChI=1S/C16H23N5O6/c1-8(2-3-17-14-10-15(19-6-18-10)21-7-20-14)5-26-16-13(25)12(24)11(23)9(4-22)27-16/h2,6-7,9,11-13,16,22-25H,3-5H2,1H3,(H2,17,18,19,20,21)/b8-2+</inchi>
  <inchikey>UUPDCCPAOMDMPT-KRXBUXKQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.</description>
    <direct_parent>Fatty acyl glycosides of mono- and disaccharides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl glycosides</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>6-alkylaminopurines</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-alkylaminopurine</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Fatty acyl glycoside of mono- or disaccharide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</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>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.69e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 124-128?</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>5.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-(hydroxymethyl)-6-{[(2E)-2-methyl-4-[(9H-purin-6-yl)amino]but-2-en-1-yl]oxy}oxane-3,4,5-triol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>381.3837</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>381.164833493</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C\C(COC1OC(CO)C(O)C(O)C1O)=C/CNC1=NC=NC2=C1N=CN2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H23N5O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H23N5O6/c1-8(2-3-17-14-10-15(19-6-18-10)21-7-20-14)5-26-16-13(25)12(24)11(23)9(4-22)27-16/h2,6-7,9,11-13,16,22-25H,3-5H2,1H3,(H2,17,18,19,20,21)/b8-2+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>UUPDCCPAOMDMPT-KRXBUXKQSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>165.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>95.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>39.07</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>7</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>0</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>1262824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1262825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1262826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1377925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1377926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1377927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3606706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3606707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3606708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3606709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3606710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3606711</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
