<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:44 UTC</creation_date>
  <update_date>2020-02-24 19:10:15 UTC</update_date>
  <accession>FDB000861</accession>
  <name>Diosmetin</name>
  <description>Isolated from peel of lemon (Citrus limon) and others. Diosmetin is found in many foods, some of which are spearmint, citrus, rosemary, and common thyme.</description>
  <synonyms>
    <synonym>3',5,7-Trihydroxy-4'-methoxyflavone</synonym>
    <synonym>4'-Methylluteolin</synonym>
    <synonym>5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone</synonym>
    <synonym>5,7,3'-Trihydroxy-4'-methoxyflavone</synonym>
    <synonym>Diosmetin</synonym>
    <synonym>Luteolin 4'-methyl ether</synonym>
    <synonym>Salinigricoflavonol</synonym>
    <synonym>Vitamin P</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-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one</iupac_name>
  <traditional_iupac>diosmetin</traditional_iupac>
  <cas_registry_number>520-34-3</cas_registry_number>
  <smiles>COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O</smiles>
  <inchi>InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3</inchi>
  <inchikey>MBNGWHIJMBWFHU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.</description>
    <direct_parent>4'-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>3'-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>3'-hydroxyflavonoid</substituent>
      <substituent>4p-methoxyflavonoid-skeleton</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>3'-hydroxyflavonoid</external_descriptor>
      <external_descriptor>Flavones and Flavonols</external_descriptor>
      <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>3.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.54e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 228-230°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>6.64</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-(3-hydroxy-4-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=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H12O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MBNGWHIJMBWFHU-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>29.84</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>5958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>41510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>157793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236763</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB29676</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>4630</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31dd6530&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Citrus</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Common oregano</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum vulgare</name_scientific>
      <ncbi_taxonomy_id>39352</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>Dill</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anethum graveolens</name_scientific>
      <ncbi_taxonomy_id>40922</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Hyssop</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hyssopus officinalis</name_scientific>
      <ncbi_taxonomy_id>39324</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Lemon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus limon</name_scientific>
      <ncbi_taxonomy_id>2708</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Lemon verbena</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Aloysia triphylla</name_scientific>
      <ncbi_taxonomy_id>542672</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rosemary</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rosmarinus officinalis</name_scientific>
      <ncbi_taxonomy_id>39367</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Spearmint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha spicata</name_scientific>
      <ncbi_taxonomy_id>29719</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet marjoram</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum majorana</name_scientific>
      <ncbi_taxonomy_id>268884</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-Alzheimeran</name>
      <id>105</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-dementia</name>
      <id>222</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</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_effect>
      <name>Estrogenic</name>
      <id>922</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Nitric-oxide inhibitor</name>
      <id>1167</id>
      <definition>A substance that diminishes the rate of a chemical reaction.</definition>
    </health_effect>
    <health_effect>
      <name>Osteoblastogenic</name>
      <id>1177</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Peroxisome proliferator activated receptor gamma antagonist</name>
      <id>1239</id>
      <definition>Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.</definition>
    </health_effect>
    <health_effect>
      <name>TNF-alpha inhibitor</name>
      <id>1363</id>
      <definition>A substance that diminishes the rate of a chemical reaction.</definition>
    </health_effect>
  </health_effects>
</compound>
