<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:56 UTC</creation_date>
  <update_date>2025-11-19 00:37:04 UTC</update_date>
  <accession>FDB013850</accession>
  <name>Dukunolide C</name>
  <description>From Lansium domesticum (langsat). Dukunolide C is found in fruits.</description>
  <synonyms>
    <synonym>(+)-Dukunolide C</synonym>
    <synonym>Dukunolide C</synonym>
  </synonyms>
  <chemical_formula>C28H28O11</chemical_formula>
  <average_molecular_weight>540.5153</average_molecular_weight>
  <monisotopic_moleculate_weight>540.163161738</monisotopic_moleculate_weight>
  <iupac_name>18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-dien-12-yl acetate</iupac_name>
  <traditional_iupac>18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-dien-12-yl acetate</traditional_iupac>
  <cas_registry_number>99343-74-5</cas_registry_number>
  <smiles>CC(=O)OC1C2=CCCC3(C)C(OC(=O)C(=C23)C2(O)C3(C)OC(=O)C4OC34C(C)(C)C(=O)C12O)C1=COC=C1</smiles>
  <inchi>InChI=1S/C28H28O11/c1-12(29)36-18-14-7-6-9-24(4)15(14)16(20(30)37-17(24)13-8-10-35-11-13)27(34)25(5)28(19(38-28)21(31)39-25)23(2,3)22(32)26(18,27)33/h7-8,10-11,17-19,33-34H,6,9H2,1-5H3</inchi>
  <inchikey>HOJFTRARYIFTJU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon  made up of two fused benzene rings.</description>
    <direct_parent>Naphthopyrans</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Naphthopyrans</class>
    <sub_class/>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1,4-dioxanes</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Dihydropyranones</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Furans</alternative_parent>
      <alternative_parent>Gamma butyrolactones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Naphthalenes</alternative_parent>
      <alternative_parent>Naphthofurans</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Dihydropyranone</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Ether</substituent>
      <substituent>Furan</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Lactone</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Naphthofuran</substituent>
      <substituent>Naphthopyran</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxirane</substituent>
      <substituent>Para-dioxane</substituent>
      <substituent>Pyran</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.11e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 217-218°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-dien-12-yl acetate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>540.5153</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>540.163161738</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(=O)OC1C2=CCCC3(C)C(OC(=O)C(=C23)C2(O)C3(C)OC(=O)C4OC34C(C)(C)C(=O)C12O)C1=COC=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C28H28O11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C28H28O11/c1-12(29)36-18-14-7-6-9-24(4)15(14)16(20(30)37-17(24)13-8-10-35-11-13)27(34)25(5)28(19(38-28)21(31)39-25)23(2,3)22(32)26(18,27)33/h7-8,10-11,17-19,33-34H,6,9H2,1-5H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HOJFTRARYIFTJU-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>162.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>127.49</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>51.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</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>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>25761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>264561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>264562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>264563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>264564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>264565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>281334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>135171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>135172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>135173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2346275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2346276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2346277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2592781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2592782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2592783</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB35204</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:0x000055ce32feae88&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>
