<?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 22:38:04 UTC</update_date>
  <accession>FDB002523</accession>
  <name>Quercetin 7-glucoside</name>
  <description>Quercetin 7-glucoside, also known as quercimeritrin, 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 7-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 7-glucoside can be found in a number of food items such as roman camomile, okra, dandelion, and cottonseed, which makes quercetin 7-glucoside a potential biomarker for the consumption of these food products. </description>
  <synonyms>
    <synonym>7-Glucosyl quercetin</synonym>
    <synonym>7-O-b-D-Glucopyranosyloxy-3,3',4',5-tetrahydroxyflavone</synonym>
    <synonym>Glucosyl-7-quercetin</synonym>
    <synonym>Quercetin 7-&amp;beta;-D-glucopyranoside</synonym>
    <synonym>Quercetin 7-&amp;beta;-D-glucoside</synonym>
    <synonym>Quercetin 7-glucoside</synonym>
    <synonym>Quercetin 7-monoglucoside</synonym>
    <synonym>Quercetin 7-O-&amp;beta;-D-glucopyranoside</synonym>
    <synonym>Quercetin 7-O-beta-D-glucoside</synonym>
    <synonym>Quercetin 7-O-glucoside</synonym>
    <synonym>Quercimeritrin</synonym>
    <synonym>Quercimeritroside</synonym>
  </synonyms>
  <chemical_formula>C21H20O12</chemical_formula>
  <average_molecular_weight>464.3763</average_molecular_weight>
  <monisotopic_moleculate_weight>464.095476104</monisotopic_moleculate_weight>
  <iupac_name>2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one</iupac_name>
  <traditional_iupac>quercimeritrin</traditional_iupac>
  <cas_registry_number>491-50-9</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1</inchi>
  <inchikey>BBFYUPYFXSSMNV-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>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>Catechols</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'-hydroxyflavonoid</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>Catechol</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>Flavones and Flavonols</external_descriptor>
      <external_descriptor>beta-D-glucoside</external_descriptor>
      <external_descriptor>flavonols</external_descriptor>
      <external_descriptor>flavonols</external_descriptor>
      <external_descriptor>monosaccharide derivative</external_descriptor>
      <external_descriptor>quercetin O-glucoside</external_descriptor>
      <external_descriptor>tetrahydroxyflavone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.61e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 249-250°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>7.98</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-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>464.3763</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>464.095476104</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C21H20O12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BBFYUPYFXSSMNV-HMGRVEAOSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>206.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>109.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>43.89</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>8</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>105225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599109</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28529</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Black tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <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>Cottonseed</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gossypium</name_scientific>
      <ncbi_taxonomy_id>3633</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Dandelion</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Taraxacum officinale</name_scientific>
      <ncbi_taxonomy_id>50225</ncbi_taxonomy_id>
    </food>
    <food>
      <name>German camomile</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Matricaria recutita</name_scientific>
      <ncbi_taxonomy_id>127986</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Green tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Herbal tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Okra</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Abelmoschus esculentus</name_scientific>
      <ncbi_taxonomy_id>455045</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pomegranate</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Punica granatum</name_scientific>
      <ncbi_taxonomy_id>22663</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Red tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Roman camomile</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Chamaemelum nobile</name_scientific>
      <ncbi_taxonomy_id>99037</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sunflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Helianthus annuus</name_scientific>
      <ncbi_taxonomy_id>4232</ncbi_taxonomy_id>
      <average_value>2.2</average_value>
      <max_value>2.2</max_value>
      <min_value>2.2</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Tea</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Camellia sinensis</name_scientific>
      <ncbi_taxonomy_id>4442</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Aldose reductase inhibitor</name>
      <id>40</id>
      <definition>An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).</definition>
    </health_effect>
    <health_effect>
      <name>Anti-herpetic</name>
      <id>329</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-viral</name>
      <id>689</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Insectiphile</name>
      <id>1042</id>
      <definition>Strictly, a substance intended to kill members of the class Insecta.  In common usage, any substance used for preventing, destroying, repelling or controlling insects.</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>
