<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:59 UTC</creation_date>
  <update_date>2020-02-24 19:10:23 UTC</update_date>
  <accession>FDB001472</accession>
  <name>Sakuranetin</name>
  <description>Sakuranetin is a flavanone, a type of flavonoid. It can be found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae.</description>
  <synonyms>
    <synonym>(2S)-Sakuranetin</synonym>
    <synonym>(S)-(-)-4',5-Dihydroxy-7-methoxyflavanone</synonym>
    <synonym>(S)-2,3-dihydro-5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one</synonym>
    <synonym>4',5-Dihydroxy-7-methoxyflavanone</synonym>
    <synonym>5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-one</synonym>
    <synonym>5,4'-Dihydroxy-7-methoxyflavanone</synonym>
    <synonym>7-O-Methylnaringenin</synonym>
    <synonym>Naringenin 7-methyl ether</synonym>
  </synonyms>
  <chemical_formula>C16H14O5</chemical_formula>
  <average_molecular_weight>286.2794</average_molecular_weight>
  <monisotopic_moleculate_weight>286.084123558</monisotopic_moleculate_weight>
  <iupac_name>(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one</iupac_name>
  <traditional_iupac>sakuranetin</traditional_iupac>
  <cas_registry_number>2957-21-3</cas_registry_number>
  <smiles>[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1</inchi>
  <inchikey>DJOJDHGQRNZXQQ-AWEZNQCLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.</description>
    <direct_parent>7-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>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Flavanones</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-methoxyflavonoid-skeleton</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</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>Flavan</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>Flavanones</external_descriptor>
      <external_descriptor>dihydroxyflavanone</external_descriptor>
      <external_descriptor>flavanones</external_descriptor>
      <external_descriptor>flavonoid phytoalexin</external_descriptor>
      <external_descriptor>monomethoxyflavanone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.83e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>152 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.98</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>286.2794</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>286.084123558</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H14O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DJOJDHGQRNZXQQ-AWEZNQCLSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>75.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>75.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>29.41</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</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>11257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>41740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>100535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>100536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>151810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2226595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2230509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2230520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2231250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2233652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2233684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2235262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2235278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2252494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2253973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2258552</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB30090</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28927</chebi_id>
  <biocyc_id/>
  <het_id>SAK</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31f0e358&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31f0e1a0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Black walnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Juglans nigra</name_scientific>
      <ncbi_taxonomy_id>16719</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Blackcurrant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ribes nigrum</name_scientific>
      <ncbi_taxonomy_id>78511</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota ssp. sativus</name_scientific>
      <ncbi_taxonomy_id>79200</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mexican oregano</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lippia graveolens</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>93.0</average_value>
      <max_value>93.0</max_value>
      <min_value>93.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Prunus (Cherry, Plum)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus</name_scientific>
      <ncbi_taxonomy_id>3754</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>Walnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Juglans</name_scientific>
      <ncbi_taxonomy_id>16718</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota</name_scientific>
      <ncbi_taxonomy_id>4039</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti bacterial</name>
      <id>145</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti septic</name>
      <id>603</id>
      <definition>A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.</definition>
    </health_effect>
    <health_effect>
      <name>Fungicide</name>
      <id>940</id>
      <definition>A substance used to destroy fungal pests.</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>
