<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:38 UTC</creation_date>
  <update_date>2025-11-18 23:27:24 UTC</update_date>
  <accession>FDB011428</accession>
  <name>3,5,7-Trihydroxy-4'-methoxy-8-prenylflavone 3-[rhamnosyl-(1-&gt;6)-galactoside] 7-galactoside</name>
  <description>Constituent of Sesbania grandiflora (agati). 3,5,7-Trihydroxy-4'-methoxy-8-prenylflavone 3-[rhamnosyl-(1-&gt;6)-galactoside] 7-galactoside is found in fruits.</description>
  <synonyms>
    <synonym>3,5,7-Trihydroxy-4'-methoxy-8-prenylflavone 3-[rhamnosyl-(1-&gt;6)-galactoside] 7-galactoside</synonym>
    <synonym>3,5,7-Trihydroxy-4'-methoxy-8-prenylflavone 3-O-[a-L-rhamnopyranosyl-(1-&gt;6)-b-D-galactopyranoside] 7-O-b-D-galactopyranoside</synonym>
    <synonym>4'-Methylnoranhydroicaritin 3-[rhamnosyl-(1-&gt;6)-galactoside] 7-galactoside</synonym>
  </synonyms>
  <chemical_formula>C39H50O20</chemical_formula>
  <average_molecular_weight>838.8023</average_molecular_weight>
  <monisotopic_moleculate_weight>838.28954404</monisotopic_moleculate_weight>
  <iupac_name>5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one</iupac_name>
  <traditional_iupac>5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]chromen-4-one</traditional_iupac>
  <cas_registry_number>328-39-2</cas_registry_number>
  <smiles>COC1=CC=C(C=C1)C1=C(OC2OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C2O)C(=O)C2=C(O1)C(CC=C(C)C)=C(OC1OC(CO)C(O)C(O)C1O)C=C2O</smiles>
  <inchi>InChI=1S/C39H50O20/c1-14(2)5-10-18-20(55-38-32(50)29(47)25(43)21(12-40)56-38)11-19(41)23-27(45)36(34(58-35(18)23)16-6-8-17(52-4)9-7-16)59-39-33(51)30(48)26(44)22(57-39)13-53-37-31(49)28(46)24(42)15(3)54-37/h5-9,11,15,21-22,24-26,28-33,37-44,46-51H,10,12-13H2,1-4H3</inchi>
  <inchikey>SFPBPCAQVDGNMT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.</description>
    <direct_parent>Flavonoid-7-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>4'-O-methylated flavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>8-prenylated flavones</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Flavonoid-3-O-glycosides</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</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>Phenolic glycosides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyranones 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>4p-methoxyflavonoid-skeleton</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>8-prenylated flavone</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromone</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Ether</substituent>
      <substituent>Flavone</substituent>
      <substituent>Flavonoid-3-o-glycoside</substituent>
      <substituent>Flavonoid-7-o-glycoside</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyflavonoid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocyclic benzene moiety</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 ether</substituent>
      <substituent>Phenolic glycoside</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.71e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 214-217°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>8.27</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-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>838.8023</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>838.28954404</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC=C(C=C1)C1=C(OC2OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C2O)C(=O)C2=C(O1)C(CC=C(C)C)=C(OC1OC(CO)C(O)C(O)C1O)C=C2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C39H50O20</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C39H50O20/c1-14(2)5-10-18-20(55-38-32(50)29(47)25(43)21(12-40)56-38)11-19(41)23-27(45)36(34(58-35(18)23)16-6-8-17(52-4)9-7-16)59-39-33(51)30(48)26(44)22(57-39)13-53-37-31(49)28(46)24(42)15(3)54-37/h5-9,11,15,21-22,24-26,28-33,37-44,46-51H,10,12-13H2,1-4H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>SFPBPCAQVDGNMT-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>313.44</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>199.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>83.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>20</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>11</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::NmrOneD</type>
      <spectrum_id>119658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>119677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2396841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2396842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2396843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2542349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2542350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2542351</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB33395</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:0x000055ce3212e930&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Fruits</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>
