<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:12:28 UTC</creation_date>
  <update_date>2025-11-19 01:47:28 UTC</update_date>
  <accession>FDB016495</accession>
  <name>Kaempferol 7-glucoside</name>
  <description>Kaempferol 7-glucoside 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. Kaempferol 7-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 7-glucoside can be found in a number of food items such as flaxseed, ginkgo nuts, white cabbage, and saffron, which makes kaempferol 7-glucoside a potential biomarker for the consumption of these food products. </description>
  <synonyms>
    <synonym>7-O-b-D-Glucopyranosyloxy-3,4',5-trihydroxyflavone</synonym>
    <synonym>Kaempferol 7-b-D-glucoside</synonym>
    <synonym>Kaempferol 7-beta-D-glucoside</synonym>
    <synonym>Kaempferol 7-O-beta-D-glucopyranoside</synonym>
    <synonym>Kaempferol 7-O-glucoside</synonym>
    <synonym>Populnin</synonym>
  </synonyms>
  <chemical_formula>C21H20O11</chemical_formula>
  <average_molecular_weight>448.3769</average_molecular_weight>
  <monisotopic_moleculate_weight>448.100561482</monisotopic_moleculate_weight>
  <iupac_name>3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one</iupac_name>
  <traditional_iupac>3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one</traditional_iupac>
  <cas_registry_number>16290-07-6</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](OC2=CC3=C(C(O)=C2)C(=O)C(O)=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21-/m1/s1</inchi>
  <inchikey>YPWHZCPMOQGCDQ-HMGRVEAOSA-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>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>3-hydroxyflavonoids</alternative_parent>
      <alternative_parent>4'-hydroxyflavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Flavonols</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Phenolic glycosides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyranones and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-hydroxyflavone</substituent>
      <substituent>3-hydroxyflavonoid</substituent>
      <substituent>4'-hydroxyflavonoid</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromone</substituent>
      <substituent>Flavone</substituent>
      <substituent>Flavonoid-7-o-glycoside</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyflavonoid</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenolic glycoside</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>beta-D-glucoside</external_descriptor>
      <external_descriptor>flavonols</external_descriptor>
      <external_descriptor>kaempferol O-glucoside</external_descriptor>
      <external_descriptor>monosaccharide derivative</external_descriptor>
      <external_descriptor>trihydroxyflavone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.30e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 250°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.19</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>8.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3,5-dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>448.3769</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>448.100561482</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H]1O[C@@H](OC2=CC3=C(C(O)=C2)C(=O)C(O)=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C21H20O11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>YPWHZCPMOQGCDQ-HMGRVEAOSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>186.37</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>107.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>43.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</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::MsMs</type>
      <spectrum_id>52590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605994</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>Blackberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>7.3</average_value>
      <max_value>7.3</max_value>
      <min_value>7.3</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Broad bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vicia faba</name_scientific>
      <ncbi_taxonomy_id>3906</ncbi_taxonomy_id>
      <average_value>0.03625</average_value>
      <max_value>0.0665</max_value>
      <min_value>0.006</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea var. capitata</name_scientific>
      <ncbi_taxonomy_id>3716</ncbi_taxonomy_id>
    </food>
    <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>
    </food>
    <food>
      <name>Flaxseed</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Linum usitatissimum</name_scientific>
      <ncbi_taxonomy_id>4006</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ginkgo nuts</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ginkgo biloba</name_scientific>
      <ncbi_taxonomy_id>3311</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Moth bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vigna aconitifolia</name_scientific>
      <ncbi_taxonomy_id>3918</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Saffron</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Crocus sativus</name_scientific>
      <ncbi_taxonomy_id>82528</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet cherry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus avium</name_scientific>
      <ncbi_taxonomy_id>42229</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Tropical highland blackberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus adenotrichos</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>7.3</average_value>
      <max_value>7.3</max_value>
      <min_value>7.3</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>White cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea L. var. capitata L. f. alba DC.</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti-inflammatory</name>
      <id>370</id>
      <definition>A substance that reduces or suppresses inflammation.</definition>
    </health_effect>
  </health_effects>
</compound>
