<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:30 UTC</creation_date>
  <update_date>2025-11-18 22:40:18 UTC</update_date>
  <accession>FDB002751</accession>
  <name>Nevadensin</name>
  <description>Nevadensin, also known as pedunculin or 5,7-hydroxy-4',6,8-trimethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, nevadensin is considered to be a flavonoid lipid molecule. Nevadensin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Nevadensin can be found in peppermint and sweet basil, which makes nevadensin a potential biomarker for the consumption of these food products. </description>
  <synonyms>
    <synonym>5,7-Dihydroxy-4',6,8-trimethoxyflavone</synonym>
    <synonym>Lysionotin</synonym>
    <synonym>Nevadensin</synonym>
    <synonym>Nevadensin a</synonym>
    <synonym>Nevadensin?</synonym>
    <synonym>Pedunculin</synonym>
  </synonyms>
  <chemical_formula>C18H16O7</chemical_formula>
  <average_molecular_weight>344.3154</average_molecular_weight>
  <monisotopic_moleculate_weight>344.089602866</monisotopic_moleculate_weight>
  <iupac_name>5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one</iupac_name>
  <traditional_iupac>nevadensin</traditional_iupac>
  <cas_registry_number>10176-66-6</cas_registry_number>
  <smiles>COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O</smiles>
  <inchi>InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)12-8-11(19)13-14(20)17(23-2)15(21)18(24-3)16(13)25-12/h4-8,20-21H,1-3H3</inchi>
  <inchikey>KRFBMPVGAYGGJE-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>4'-O-methylated flavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>6-O-methylated flavonoids</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>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>4p-methoxyflavonoid-skeleton</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>6-methoxyflavonoid-skeleton</substituent>
      <substituent>7-hydroxyflavonoid</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_descriptor>Flavones and Flavonols</external_descriptor>
      <external_descriptor>dihydroxyflavone</external_descriptor>
      <external_descriptor>flavones</external_descriptor>
      <external_descriptor>trimethoxyflavone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.52e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 198-199°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.54</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>6.63</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>344.3154</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>344.089602866</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H16O7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)12-8-11(19)13-14(20)17(23-2)15(21)18(24-3)16(13)25-12/h4-8,20-21H,1-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>KRFBMPVGAYGGJE-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>94.45</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>90.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>34.73</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</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>115727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>950425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>950426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>950427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>950428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>950429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>950430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2238780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2240763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2240914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243036</spectrum_id>
    </spectrum>
  </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>Peppermint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha X piperita</name_scientific>
      <ncbi_taxonomy_id>34256</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</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-inflammatory</name>
      <id>370</id>
      <definition>A substance that reduces or suppresses inflammation.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-tubercular</name>
      <id>670</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-tussive</name>
      <id>674</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Expectorant</name>
      <id>925</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</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>
