<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:26 UTC</creation_date>
  <update_date>2020-02-24 19:10:33 UTC</update_date>
  <accession>FDB002579</accession>
  <name>Chrysoeriol</name>
  <description>Widespread flavone. Chrysoeriol is found in many foods, some of which are peanut, german camomile, tarragon, and alfalfa.</description>
  <synonyms>
    <synonym>2-(5-methoxy,4-hydroxyphenyl)5,7-dihydroxy-benzpyran-4-one</synonym>
    <synonym>3'-Methoxy-4',5,7-trihydroxyflavone</synonym>
    <synonym>3'-Methoxyapigenin</synonym>
    <synonym>3'-O-Methylluteolin</synonym>
    <synonym>3'-O-Methyluteolin</synonym>
    <synonym>4',5,7-Trihydroxy-3'-methoxy-flavone</synonym>
    <synonym>5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone</synonym>
    <synonym>5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one</synonym>
    <synonym>5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one, 9CI</synonym>
    <synonym>5,7,4'-Trihydroxy-3'-methoxyflavone</synonym>
    <synonym>Chryseriol</synonym>
    <synonym>Chrysoeriol</synonym>
    <synonym>Flavone, 4',5,7-trihydroxy-3'-methoxy-</synonym>
    <synonym>Luteolin 3'-methyl ether</synonym>
    <synonym>Scoparol</synonym>
  </synonyms>
  <chemical_formula>C16H12O6</chemical_formula>
  <average_molecular_weight>300.2629</average_molecular_weight>
  <monisotopic_moleculate_weight>300.063388116</monisotopic_moleculate_weight>
  <iupac_name>5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one</iupac_name>
  <traditional_iupac>chrysoeriol</traditional_iupac>
  <cas_registry_number>491-71-4</cas_registry_number>
  <smiles>COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1</smiles>
  <inchi>InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3</inchi>
  <inchikey>SCZVLDHREVKTSH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.</description>
    <direct_parent>3'-O-methylated flavonoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Flavonoids</class>
    <sub_class>O-methylated flavonoids</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>Anisoles</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Flavones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Pyranones and derivatives</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>3p-methoxyflavonoid-skeleton</substituent>
      <substituent>4'-hydroxyflavonoid</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>7-hydroxyflavonoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromone</substituent>
      <substituent>Ether</substituent>
      <substituent>Flavone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyflavonoid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</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>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Flavones and Flavonols</external_descriptor>
      <external_descriptor>flavones</external_descriptor>
      <external_descriptor>monomethoxyflavone</external_descriptor>
      <external_descriptor>trihydroxyflavone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.84e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 330-331°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>6.58</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>300.2629</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>300.063388116</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H12O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>SCZVLDHREVKTSH-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>96.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>79.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>29.74</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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::CMs</type>
      <spectrum_id>5776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>167153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449558</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB30667</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>16514</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3164d9d0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3164d818&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Alfalfa</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Medicago sativa</name_scientific>
      <ncbi_taxonomy_id>3879</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Amaranth</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Amaranthus</name_scientific>
      <ncbi_taxonomy_id>3564</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Annual wild rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zizania aquatica</name_scientific>
      <ncbi_taxonomy_id>75727</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Barley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hordeum vulgare</name_scientific>
      <ncbi_taxonomy_id>4513</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Breakfast cereal</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Bulgur</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Cereals and cereal products</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Common buckwheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Fagopyrum esculentum</name_scientific>
      <ncbi_taxonomy_id>3617</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common sage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Salvia officinalis</name_scientific>
      <ncbi_taxonomy_id>38868</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common thyme</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Thymus vulgaris</name_scientific>
      <ncbi_taxonomy_id>49992</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum aestivum</name_scientific>
      <ncbi_taxonomy_id>4565</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Flour</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <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>Hard wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum durum</name_scientific>
      <ncbi_taxonomy_id>4567</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Millet</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Panicum miliaceum</name_scientific>
      <ncbi_taxonomy_id>4540</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Oat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Avena sativa</name_scientific>
      <ncbi_taxonomy_id>4498</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Oriental wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum turanicum</name_scientific>
      <ncbi_taxonomy_id>376534</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Peanut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Arachis hypogaea</name_scientific>
      <ncbi_taxonomy_id>3818</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quinoa</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Chenopodium quinoa</name_scientific>
      <ncbi_taxonomy_id>63459</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Red rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza rufipogon</name_scientific>
      <ncbi_taxonomy_id>4529</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza sativa</name_scientific>
      <ncbi_taxonomy_id>4530</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rye</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Secale cereale</name_scientific>
      <ncbi_taxonomy_id>4550</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sorghum</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sorghum bicolor</name_scientific>
      <ncbi_taxonomy_id>4558</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Spelt</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum spelta</name_scientific>
      <ncbi_taxonomy_id>58933</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Tarragon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Artemisia dracunculus</name_scientific>
      <ncbi_taxonomy_id>72341</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Tartary buckwheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Fagopyrum tataricum</name_scientific>
      <ncbi_taxonomy_id>62330</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Teff</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Eragrostis tef</name_scientific>
      <ncbi_taxonomy_id>110835</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Triticale</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>X Triticosecale rimpaui</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum</name_scientific>
      <ncbi_taxonomy_id>4564</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild celery</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Apium graveolens</name_scientific>
      <ncbi_taxonomy_id>4045</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zizania</name_scientific>
      <ncbi_taxonomy_id>15949</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>bitter</name>
    </flavor>
  </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 complementary</name>
      <id>201</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-mutagenic</name>
      <id>451</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-oxidant</name>
      <id>502</id>
      <definition>A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-rhinoviral</name>
      <id>588</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>Cancer preventive</name>
      <id>754</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
  </health_effects>
</compound>
