<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:19 UTC</creation_date>
  <update_date>2025-11-18 23:39:05 UTC</update_date>
  <accession>FDB012726</accession>
  <name>Myricetin 3-rhamnoside</name>
  <description>Myricitrin is a chemical compound. It can be isolated from the root bark of Myrica cerifera (Bayberry, a small tree native to North America). Myricetin 3-rhamnoside is found in many foods, some of which are common grape, black walnut, highbush blueberry, and lentils.</description>
  <synonyms>
    <synonym>Flavone,3,3',4',5,5',7-hexahydroxy-,3-rhamnoside</synonym>
    <synonym>Myricetin 3-O-alpha-L-rhamnopyranoside</synonym>
    <synonym>Myricetin 3-O-alpha-L-rhamnoside</synonym>
    <synonym>Myricetin 3-O-L-rhamnoside</synonym>
    <synonym>Myricetin 3-O-rhamnoside</synonym>
    <synonym>Myricetin 3-rhamnoside</synonym>
    <synonym>Myricetin-3-O-alpha-L-rhamnoside</synonym>
    <synonym>Myricetol 3-rhamnoside</synonym>
    <synonym>Myricetrin</synonym>
    <synonym>Myricitrin</synonym>
    <synonym>Myricitrin (8ci)</synonym>
    <synonym>Myricitrine</synonym>
    <synonym>Myricitroside</synonym>
    <synonym>Rhamnoside,myricetin-3</synonym>
  </synonyms>
  <chemical_formula>C21H20O12</chemical_formula>
  <average_molecular_weight>464.3763</average_molecular_weight>
  <monisotopic_moleculate_weight>464.095476104</monisotopic_moleculate_weight>
  <iupac_name>5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one</iupac_name>
  <traditional_iupac>myricitrin</traditional_iupac>
  <cas_registry_number>17912-87-7</cas_registry_number>
  <smiles>CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3</inchi>
  <inchikey>DCYOADKBABEMIQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.</description>
    <direct_parent>Flavonoid-3-O-glycosides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Flavonoids</class>
    <sub_class>Flavonoid glycosides</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>4'-hydroxyflavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>7-hydroxyflavonoids</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Flavones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyranones and derivatives</alternative_parent>
      <alternative_parent>Pyrogallols and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</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>4'-hydroxyflavonoid</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>7-hydroxyflavonoid</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenetriol</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromone</substituent>
      <substituent>Flavone</substituent>
      <substituent>Flavonoid-3-o-glycoside</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyflavonoid</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phenol</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Pyrogallol derivative</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.43e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 194-197°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>6.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>464.3763</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>464.095476104</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C21H20O12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DCYOADKBABEMIQ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>206.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>109.71</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>43.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>8</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>12230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>118350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>972831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081509</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB34360</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>544021</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce320aab30&gt;</reference>
    <reference>#&lt;Reference:0x000055ce320aa978&gt;</reference>
    <reference>#&lt;Reference:0x000055ce320aa680&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>Common grape</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vitis vinifera</name_scientific>
      <ncbi_taxonomy_id>29760</ncbi_taxonomy_id>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Common hazelnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Corylus avellana</name_scientific>
      <ncbi_taxonomy_id>13451</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Highbush blueberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vaccinium corymbosum</name_scientific>
      <ncbi_taxonomy_id>69266</ncbi_taxonomy_id>
      <average_value>1.035</average_value>
      <max_value>1.035000026</max_value>
      <min_value>1.035000026</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Lentils</name>
      <food_type>Type 1</food_type>
      <category>generic</category>
      <name_scientific>Lens culinaris</name_scientific>
      <ncbi_taxonomy_id>3864</ncbi_taxonomy_id>
      <average_value>0.2895</average_value>
      <max_value>0.578999996</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Rubus (Blackberry, Raspberry)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rubus</name_scientific>
      <ncbi_taxonomy_id>23216</ncbi_taxonomy_id>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sapodilla</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Manilkara zapota</name_scientific>
      <ncbi_taxonomy_id>3741</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Summer grape</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vitis aestivalis</name_scientific>
      <ncbi_taxonomy_id>3605</ncbi_taxonomy_id>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </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 bacterial</name>
      <id>145</id>
      <definition>A substance that kills or slows the growth of bacteria.</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-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>Antitumor promoter</name>
      <id>673</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Candidicide</name>
      <id>756</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Choleretic</name>
      <id>801</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Diuretic</name>
      <id>883</id>
      <definition>An agent that promotes the excretion of urine through its effects on kidney function.</definition>
    </health_effect>
    <health_effect>
      <name>Paramecicide</name>
      <id>1197</id>
      <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_effect>
      <name>Protisticide</name>
      <id>1266</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Spermicide</name>
      <id>1322</id>
      <definition/>
    </health_effect>
  </health_effects>
</compound>
