<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:12:35 UTC</creation_date>
  <update_date>2025-11-19 01:49:08 UTC</update_date>
  <accession>FDB016687</accession>
  <name>Naringenin fructoside</name>
  <description>Isolated from Camellia sinensis (tea). Naringenin fructoside is found in tea.</description>
  <synonyms>
    <synonym>(S)-4',5,7-Trihydroxyflavanone O-fructoside</synonym>
    <synonym>Naringenin fructoside</synonym>
  </synonyms>
  <chemical_formula>C15H12O5</chemical_formula>
  <average_molecular_weight>272.256</average_molecular_weight>
  <monisotopic_moleculate_weight>272.068473486</monisotopic_moleculate_weight>
  <iupac_name>5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one</iupac_name>
  <traditional_iupac>asahina</traditional_iupac>
  <cas_registry_number>24667-03-6</cas_registry_number>
  <smiles>OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1</smiles>
  <inchi>InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2</inchi>
  <inchikey>FTVWIRXFELQLPI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.</description>
    <direct_parent>Flavanones</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Flavonoids</class>
    <sub_class>Flavans</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>4'-hydroxyflavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>7-hydroxyflavonoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</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>4'-hydroxyflavonoid</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>7-hydroxyflavonoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromane</substituent>
      <substituent>Chromone</substituent>
      <substituent>Ether</substituent>
      <substituent>Flavanone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyflavonoid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>trihydroxyflavanone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.14e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>7.86</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>272.256</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>272.068473486</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C15H12O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FTVWIRXFELQLPI-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>86.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>71.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>27.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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>109173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
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    <spectrum>
      <type>Specdb::MsMs</type>
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    <spectrum>
      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2226530</spectrum_id>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2238298</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2241248</spectrum_id>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::CMs</type>
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      <type>Specdb::CMs</type>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>167242</spectrum_id>
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      <type>Specdb::CMs</type>
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      <type>Specdb::CMs</type>
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      <type>Specdb::CMs</type>
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      <type>Specdb::CMs</type>
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      <spectrum_id>798905</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>798906</spectrum_id>
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      <spectrum_id>798907</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>798908</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>798909</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>798910</spectrum_id>
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  </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>Black tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Cherry tomato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum lycopersicum var. cerasiforme</name_scientific>
      <ncbi_taxonomy_id>195583</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fruit juice</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Garden tomato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum lycopersicum</name_scientific>
      <ncbi_taxonomy_id>4081</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Grapefruit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus X paradisi</name_scientific>
      <ncbi_taxonomy_id>37656</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>Red tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Sweet orange</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus sinensis</name_scientific>
      <ncbi_taxonomy_id>2711</ncbi_taxonomy_id>
    </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_effects>
</compound>
