<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:34 UTC</creation_date>
  <update_date>2019-11-26 03:04:47 UTC</update_date>
  <accession>FDB011298</accession>
  <name>5-Hydroxyauranetin</name>
  <description>Constituent of Citrus aurantium (Seville orange). 5-Hydroxyauranetin is found in citrus.</description>
  <synonyms>
    <synonym>4'-O-Methylcalycopterin</synonym>
    <synonym>5-Hydroxy-3,4',6,7,8-pentamethoxyflavone</synonym>
    <synonym>5-Hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-1-Benzopyran-4-one</synonym>
    <synonym>5-Hydroxy-3,6,7,8,4'-pentamethoxyflavone</synonym>
    <synonym>5-Hydroxyauranetin</synonym>
  </synonyms>
  <chemical_formula>C20H20O8</chemical_formula>
  <average_molecular_weight>388.368</average_molecular_weight>
  <monisotopic_moleculate_weight>388.115817616</monisotopic_moleculate_weight>
  <iupac_name>5-hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one</iupac_name>
  <traditional_iupac>5-hydroxyauranetin</traditional_iupac>
  <cas_registry_number>50439-46-8</cas_registry_number>
  <smiles>COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1</smiles>
  <inchi>InChI=1S/C20H20O8/c1-23-11-8-6-10(7-9-11)15-17(24-2)13(21)12-14(22)18(25-3)20(27-5)19(26-4)16(12)28-15/h6-9,22H,1-5H3</inchi>
  <inchikey>KBYYZSYVUWCARH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.</description>
    <direct_parent>8-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>3-O-methylated flavonoids</alternative_parent>
      <alternative_parent>3-methoxychromones</alternative_parent>
      <alternative_parent>4'-O-methylated flavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>6-O-methylated flavonoids</alternative_parent>
      <alternative_parent>7-O-methylated flavonoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</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>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>3-methoxychromone</substituent>
      <substituent>3-methoxyflavonoid-skeleton</substituent>
      <substituent>4p-methoxyflavonoid-skeleton</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>6-methoxyflavonoid-skeleton</substituent>
      <substituent>7-methoxyflavonoid-skeleton</substituent>
      <substituent>8-methoxyflavonoid-skeleton</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>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 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_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.36e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 125-127° (120°)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5-hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>388.368</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>388.115817616</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H20O8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H20O8/c1-23-11-8-6-10(7-9-11)15-17(24-2)13(21)12-14(22)18(25-3)20(27-5)19(26-4)16(12)28-15/h6-9,22H,1-5H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>KBYYZSYVUWCARH-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>92.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>101.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>39.56</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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::CMs</type>
      <spectrum_id>24345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>167199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2720127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2720128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2720129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2959275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2959276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2959277</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB33275</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:0x000055ce3180ad18&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Citrus</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
