<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:38 UTC</creation_date>
  <update_date>2019-11-26 03:08:16 UTC</update_date>
  <accession>FDB013294</accession>
  <name>Icariside E5</name>
  <description>Constituent of ripe fruits of Capsicum annuum  variety acuminatum. Icariside E5 is found in many foods, some of which are green bell pepper, yellow bell pepper, red bell pepper, and herbs and spices.</description>
  <synonyms>
  </synonyms>
  <chemical_formula>C26H34O11</chemical_formula>
  <average_molecular_weight>522.5416</average_molecular_weight>
  <monisotopic_moleculate_weight>522.21011193</monisotopic_moleculate_weight>
  <iupac_name>2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-[(1Z)-3-hydroxyprop-1-en-1-yl]-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-[(1Z)-3-hydroxyprop-1-en-1-yl]-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol</traditional_iupac>
  <cas_registry_number>126176-79-2</cas_registry_number>
  <smiles>COC1=CC(\C=C/CO)=CC(C(CO)CC2=CC(OC)=C(O)C=C2)=C1OC1OC(CO)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/C26H34O11/c1-34-19-10-15(5-6-18(19)30)8-16(12-28)17-9-14(4-3-7-27)11-20(35-2)25(17)37-26-24(33)23(32)22(31)21(13-29)36-26/h3-6,9-11,16,21-24,26-33H,7-8,12-13H2,1-2H3/b4-3-</inchi>
  <inchikey>UFFRBCKYXMEITK-ARJAWSKDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.</description>
    <direct_parent>Stilbene glycosides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Stilbenes</class>
    <sub_class>Stilbene glycosides</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Cinnamyl alcohols</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Phenolic glycosides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cinnamyl alcohol</substituent>
      <substituent>Ether</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenolic glycoside</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Stilbene glycoside</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.75e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-2.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-[(1Z)-3-hydroxyprop-1-en-1-yl]-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>522.5416</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>522.21011193</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC(\C=C/CO)=CC(C(CO)CC2=CC(OC)=C(O)C=C2)=C1OC1OC(CO)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C26H34O11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C26H34O11/c1-34-19-10-15(5-6-18(19)30)8-16(12-28)17-9-14(4-3-7-27)11-20(35-2)25(17)37-26-24(33)23(32)22(31)21(13-29)36-26/h3-6,9-11,16,21-24,26-33H,7-8,12-13H2,1-2H3/b4-3-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>UFFRBCKYXMEITK-ARJAWSKDSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>178.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>132.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>52.54</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>7</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::CMs</type>
      <spectrum_id>24212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146657</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB34749</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce325450a0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Fruits</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Green bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Italian sweet red pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Orange bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Red bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Yellow bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
