<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:12:24 UTC</creation_date>
  <update_date>2019-11-26 03:13:10 UTC</update_date>
  <accession>FDB016394</accession>
  <name>Vincetoxicoside A</name>
  <description>Quercetin 3-galactoside 7-rhamnoside is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Quercetin 3-galactoside 7-rhamnoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 3-galactoside 7-rhamnoside can be found in broad bean, fruits, and root vegetables, which makes quercetin 3-galactoside 7-rhamnoside a potential biomarker for the consumption of these food products. </description>
  <synonyms>
    <synonym>Peliolaroside</synonym>
    <synonym>Petiolaroside</synonym>
    <synonym>Quercetin 3-glucoside 7-rhamnoside</synonym>
    <synonym>Quercetin 3-glucoside-7-rhamnoside</synonym>
    <synonym>Quercetin 3-O-glucoside 7-O-rhamnoside</synonym>
    <synonym>Quercetol 3-glucoside 7-rhamnoside</synonym>
    <synonym>Vincetoxicoside A</synonym>
  </synonyms>
  <chemical_formula>C27H30O16</chemical_formula>
  <average_molecular_weight>610.5175</average_molecular_weight>
  <monisotopic_moleculate_weight>610.153384912</monisotopic_moleculate_weight>
  <iupac_name>2-(3,4-dihydroxyphenyl)-5-hydroxy-3-{[(2S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one</iupac_name>
  <traditional_iupac>2-(3,4-dihydroxyphenyl)-5-hydroxy-3-{[(2S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one</traditional_iupac>
  <cas_registry_number>18016-58-5</cas_registry_number>
  <smiles>CC1OC(OC2=CC(O)=C3C(=O)C(OC4OC(CO)C(O)C(O)C4O)=C(OC3=C2)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(39-8)40-10-5-13(31)16-14(6-10)41-24(9-2-3-11(29)12(30)4-9)25(19(16)34)43-27-23(38)21(36)18(33)15(7-28)42-27/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3</inchi>
  <inchikey>OTUCXMIQUNROBJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.</description>
    <direct_parent>Flavonoid-7-O-glycosides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Flavonoids</class>
    <sub_class>Flavonoid glycosides</sub_class>
    <molecular_framework name="" source="FooDB" kind=""/>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 236° (block)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>7.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-(3,4-dihydroxyphenyl)-5-hydroxy-3-{[(2S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>610.5175</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>610.153384912</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1OC(OC2=CC(O)=C3C(=O)C(OC4OC(CO)C(O)C(O)C4O)=C(OC3=C2)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C27H30O16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(39-8)40-10-5-13(31)16-14(6-10)41-24(9-2-3-11(29)12(30)4-9)25(19(16)34)43-27-23(38)21(36)18(33)15(7-28)42-27/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>OTUCXMIQUNROBJ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>265.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>139.88</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>57.58</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>10</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>
  </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>Capers</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capparis spinosa</name_scientific>
      <ncbi_taxonomy_id>65558</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Linden</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Tilia</name_scientific>
      <ncbi_taxonomy_id>64580</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Silver linden</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Tilia argentea</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
