<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:24 UTC</creation_date>
  <update_date>2025-11-18 22:37:53 UTC</update_date>
  <accession>FDB002498</accession>
  <name>epsilon-Viniferin</name>
  <description>It is a resveratrol dimer.; e-viniferin is a naturally-occurring polyphenol, belonging to the stilbenes family. It is found in grapevines, in wines and in the Oriental medicinal plant Vitis coignetiae.</description>
  <synonyms>
    <synonym>Epsilon-viniferin</synonym>
  </synonyms>
  <chemical_formula>C28H22O6</chemical_formula>
  <average_molecular_weight>454.478</average_molecular_weight>
  <monisotopic_moleculate_weight>454.141638428</monisotopic_moleculate_weight>
  <iupac_name>5-[(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol</iupac_name>
  <traditional_iupac>epsilon-viniferin</traditional_iupac>
  <cas_registry_number>62218-08-0</cas_registry_number>
  <smiles>OC1=CC=C(\C=C\C2=CC(O)=CC3=C2[C@H]([C@@H](O3)C2=CC=C(O)C=C2)C2=CC(O)=CC(O)=C2)C=C1</smiles>
  <inchi>InChI=1S/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28+/m1/s1</inchi>
  <inchikey>FQWLMRXWKZGLFI-YVYUXZJTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.</description>
    <direct_parent>2-arylbenzofuran flavonoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>2-arylbenzofuran flavonoids</class>
    <sub_class/>
    <molecular_framework>Aromatic heteropolycyclic 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>1-phenylcoumarans</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Resorcinols</alternative_parent>
      <alternative_parent>Stilbenes</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>1-phenylcoumaran</substituent>
      <substituent>2-arylbenzofuran flavonoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Coumaran</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenol</substituent>
      <substituent>Resorcinol</substituent>
      <substituent>Stilbene</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>1-benzofurans</external_descriptor>
      <external_descriptor>Stilbenoid dimers, stilbenoid oligomers and bis(bibenzyl)s</external_descriptor>
      <external_descriptor>polyphenol</external_descriptor>
      <external_descriptor>stilbenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.39e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>8.51</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5-[(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>454.478</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>454.141638428</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1=CC=C(\C=C\C2=CC(O)=CC3=C2[C@H]([C@@H](O3)C2=CC=C(O)C=C2)C2=CC(O)=CC(O)=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/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FQWLMRXWKZGLFI-YVYUXZJTSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>110.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>130.04</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>47.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>5</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>240127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242184</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>Common grape</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vitis vinifera</name_scientific>
      <ncbi_taxonomy_id>29760</ncbi_taxonomy_id>
      <average_value>3090.0</average_value>
      <max_value>3090.0</max_value>
      <min_value>3090.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Garden rhubarb</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rheum rhabarbarum</name_scientific>
      <ncbi_taxonomy_id>3621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Grape wine</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.05486</average_value>
      <max_value>0.157722223</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Red wine</name>
      <food_type>Type 2</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Rosé wine</name>
      <food_type>Type 2</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>White wine</name>
      <food_type>Type 2</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti septic</name>
      <id>603</id>
      <definition>A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.</definition>
    </health_effect>
    <health_effect>
      <name>Fungicide</name>
      <id>940</id>
      <definition>A substance used to destroy fungal pests.</definition>
    </health_effect>
    <health_effect>
      <name>Hepatoprotective</name>
      <id>981</id>
      <definition>Any compound that is able to prevent damage to the liver.</definition>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
  </health_effects>
</compound>
