<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:15:13 UTC</creation_date>
  <update_date>2019-11-26 03:19:22 UTC</update_date>
  <accession>FDB020730</accession>
  <name>Ampelopsin D</name>
  <description>Constituent of Vitis vinifera (wine grape). Ampelopsin D is found in alcoholic beverages and fruits.</description>
  <synonyms>
    <synonym>(+/-)-taxifolin</synonym>
    <synonym>3,3 ,4 ,5,7-Pentahydroxyflavonone</synonym>
    <synonym>3,3',4',5,7-Pentahydroxy-flavanone</synonym>
    <synonym>3,3',4',5,7-Pentahydroxydihydroflavone</synonym>
    <synonym>3,3',4',5',7-Pentahydroxy-flavanone</synonym>
    <synonym>Ampelopsin</synonym>
    <synonym>Dihydromyricetin</synonym>
  </synonyms>
  <chemical_formula>C28H22O6</chemical_formula>
  <average_molecular_weight>454.4707</average_molecular_weight>
  <monisotopic_moleculate_weight>454.141638436</monisotopic_moleculate_weight>
  <iupac_name>(1Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydro-1H-indene-4,6-diol</iupac_name>
  <traditional_iupac>(1Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol</traditional_iupac>
  <cas_registry_number>149418-37-1</cas_registry_number>
  <smiles>OC1=CC=C(\C=C2\C(C(C3=C2C=C(O)C=C3O)C2=CC(O)=CC(O)=C2)C2=CC=C(O)C=C2)C=C1</smiles>
  <inchi>InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(17-10-20(31)12-21(32)11-17)26(23)16-3-7-19(30)8-4-16/h1-14,26-27,29-34H/b23-9+</inchi>
  <inchikey>NJFRRNXUFGQUEK-NUGSKGIGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups  to a phenyl ring lead to stilbenoids.</description>
    <direct_parent>Stilbenes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Stilbenes</class>
    <sub_class/>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Indanes</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Resorcinols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indane</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Resorcinol</substituent>
      <substituent>Stilbene</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.51e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>8.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-5.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydro-1H-indene-4,6-diol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>454.4707</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>454.141638436</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1=CC=C(\C=C2\C(C(C3=C2C=C(O)C=C3O)C2=CC(O)=CC(O)=C2)C2=CC=C(O)C=C2)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C28H22O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(17-10-20(31)12-21(32)11-17)26(23)16-3-7-19(30)8-4-16/h1-14,26-27,29-34H/b23-9+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>NJFRRNXUFGQUEK-NUGSKGIGSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>121.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>130.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>47.88</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</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::CMs</type>
      <spectrum_id>15185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>47015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>299665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>299666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>299667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>341740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>341741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>341742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3048722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3048723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3048724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3118366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3118367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3118368</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB40894</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:0x000055ce33028788&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Alcoholic beverages</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Fruits</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>
