<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:55 UTC</creation_date>
  <update_date>2019-11-26 03:05:49 UTC</update_date>
  <accession>FDB011955</accession>
  <name>Quercetin 3-arabinoside</name>
  <description>obtained from leaves of guava (Psidium guajava ) and from other plants. Quercetin 3-arabinoside is found in many foods, some of which are star anise, common hazelnut, common walnut, and pear.</description>
  <synonyms>
    <synonym>Foeniculin</synonym>
    <synonym>Guaiaverin</synonym>
    <synonym>Guaijaverin</synonym>
    <synonym>Guajavarin</synonym>
    <synonym>Quercetin 3-arabinoside</synonym>
    <synonym>Quercetin 3-L-arabinoside</synonym>
    <synonym>Quercetin 3-O-alpha-L-arabinopyranoside</synonym>
    <synonym>Quercetin 3-O-alpha-L-arabinoside</synonym>
    <synonym>Quercetin 3-O-arabinoside</synonym>
  </synonyms>
  <chemical_formula>C20H18O11</chemical_formula>
  <average_molecular_weight>434.3503</average_molecular_weight>
  <monisotopic_moleculate_weight>434.084911418</monisotopic_moleculate_weight>
  <iupac_name>3-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one</iupac_name>
  <traditional_iupac>3-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one</traditional_iupac>
  <cas_registry_number>22255-13-6</cas_registry_number>
  <smiles>OC[C@@H]1O[C@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20+/m0/s1</inchi>
  <inchikey>BDCDNTVZSILEOY-BQCJVYABSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.</description>
    <direct_parent>Curcuminoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Diarylheptanoids</class>
    <sub_class>Linear diarylheptanoids</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Acryloyl compounds</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Beta-diketones</alternative_parent>
      <alternative_parent>Enones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxycinnamic acids and derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>1,3-diketone</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Acryloyl-group</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Alpha,beta-unsaturated ketone</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Desmethoxycurcumin</substituent>
      <substituent>Enone</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid or derivatives</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>beta-diketone</external_descriptor>
      <external_descriptor>diarylheptanoid</external_descriptor>
      <external_descriptor>enone</external_descriptor>
      <external_descriptor>polyphenol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.15e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 239° (hydrate)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.49</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>6.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>434.3503</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>434.084911418</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@@H]1O[C@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H18O11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20+/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BDCDNTVZSILEOY-BQCJVYABSA-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>103.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>41.06</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>-1</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>80196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2731165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2731166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2731167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2977109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2977110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2977111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>147517</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB33795</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:0x000055ce31cf23d0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>American cranberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vaccinium macrocarpon</name_scientific>
      <ncbi_taxonomy_id>13750</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Anise</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pimpinella anisum</name_scientific>
      <ncbi_taxonomy_id>271192</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Apple</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Malus pumila</name_scientific>
      <ncbi_taxonomy_id>283210</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bilberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vaccinium myrtillus</name_scientific>
      <ncbi_taxonomy_id>180763</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cocoa bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Theobroma cacao</name_scientific>
      <ncbi_taxonomy_id>3641</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common hazelnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Corylus avellana</name_scientific>
      <ncbi_taxonomy_id>13451</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common walnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Juglans regia</name_scientific>
      <ncbi_taxonomy_id>51240</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fennel</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Foeniculum vulgare</name_scientific>
      <ncbi_taxonomy_id>48038</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fruits</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Guava</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Psidium guajava</name_scientific>
      <ncbi_taxonomy_id>120290</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pear</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pyrus communis</name_scientific>
      <ncbi_taxonomy_id>23211</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Star anise</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Illicium verum</name_scientific>
      <ncbi_taxonomy_id>124778</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet bay</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Laurus nobilis</name_scientific>
      <ncbi_taxonomy_id>85223</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 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>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>
