<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:55 UTC</creation_date>
  <update_date>2025-11-18 23:32:32 UTC</update_date>
  <accession>FDB011964</accession>
  <name>Demethoxycurcumin</name>
  <description>Isolated from Curcuma zedoaria (zedoary), Curcuma longa (turmeric), Curcuma xanthorrhiza (Java turmeric). Demethoxycurcumin is found in many foods, some of which are beverages, herbs and spices, turmeric, and root vegetables.</description>
  <synonyms>
    <synonym>(1e,6e)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione</synonym>
    <synonym>(1e,6e)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione</synonym>
    <synonym>1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9CI</synonym>
    <synonym>4-hydroxycinnamoyl(feroyl)methane</synonym>
    <synonym>4-Hydroxycinnamoyl(feruloyl)methane</synonym>
    <synonym>Bhcfm</synonym>
    <synonym>CurcuminII</synonym>
    <synonym>Demethoxy-curcumin</synonym>
    <synonym>Demethoxycurcumin</synonym>
    <synonym>Feruloyl-p-hydroxycinnnamoylmethane</synonym>
    <synonym>Monodemethoxycurcumin</synonym>
    <synonym>p-Hydroxycinnamoylferuloylmethane</synonym>
  </synonyms>
  <chemical_formula>C20H18O5</chemical_formula>
  <average_molecular_weight>338.3539</average_molecular_weight>
  <monisotopic_moleculate_weight>338.115423686</monisotopic_moleculate_weight>
  <iupac_name>(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione</iupac_name>
  <traditional_iupac>(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione</traditional_iupac>
  <cas_registry_number>22608-11-3</cas_registry_number>
  <smiles>COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O</smiles>
  <inchi>InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+</inchi>
  <inchikey>HJTVQHVGMGKONQ-LUZURFALSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.</description>
    <direct_parent>Curcuminoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Diarylheptanoids</class>
    <sub_class>Linear diarylheptanoids</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Acryloyl compounds</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Beta-diketones</alternative_parent>
      <alternative_parent>Enones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxycinnamic acids and derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>1,3-diketone</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Acryloyl-group</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Alpha,beta-unsaturated ketone</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Desmethoxycurcumin</substituent>
      <substituent>Enone</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid or derivatives</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>beta-diketone</external_descriptor>
      <external_descriptor>diarylheptanoid</external_descriptor>
      <external_descriptor>enone</external_descriptor>
      <external_descriptor>polyphenol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.73e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 168°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.28</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>8.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>338.3539</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>338.115423686</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H18O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HJTVQHVGMGKONQ-LUZURFALSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>83.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>97.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>35.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>7</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>11172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>146439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2226658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2230441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2231460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2233861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2235067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2258675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2259907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3041914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3041915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3041916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3098311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3098312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3098313</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB33801</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:0x000055ce2ec20720&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ec20450&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ec03d00&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ec03af8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ec03698&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ec03468&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2ec03288&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Beverages</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Root vegetables</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Turmeric</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Curcuma longa</name_scientific>
      <ncbi_taxonomy_id>136217</ncbi_taxonomy_id>
      <average_value>1982.5</average_value>
      <max_value>1982.5</max_value>
      <min_value>1982.5</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti aflatoxin</name>
      <id>92</id>
      <definition>A substance that diminishes the rate of a chemical reaction.</definition>
    </health_effect>
    <health_effect>
      <name>Anti amyloid-beta</name>
      <id>109</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti leishmanic</name>
      <id>388</id>
      <definition>A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.</definition>
    </health_effect>
    <health_effect>
      <name>Anti lipoperoxidant</name>
      <id>407</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-Alzheimeran</name>
      <id>105</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-angiogenic</name>
      <id>115</id>
      <definition>An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.</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-nitrosating</name>
      <id>481</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-papillomic</name>
      <id>507</id>
      <definition>A substance that destroys or inhibits replication of viruses.</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>DNA-protective</name>
      <id>887</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Nematicide</name>
      <id>1141</id>
      <definition>A substance used to destroy pests of the phylum Nematoda (roundworms).</definition>
    </health_effect>
    <health_effect>
      <name>Nitric-oxide scavenger</name>
      <id>1168</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Plasmodicide</name>
      <id>1233</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Quinone-reductase inducer</name>
      <id>1277</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Sortase-A inhibitor</name>
      <id>1319</id>
      <definition>A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.</definition>
    </health_effect>
    <health_effect>
      <name>Topoisomerase-I inhibitor</name>
      <id>1368</id>
      <definition>A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.</definition>
    </health_effect>
    <health_effect>
      <name>Topoisomerase-II inhibitor</name>
      <id>1366</id>
      <definition>A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.</definition>
    </health_effect>
  </health_effects>
</compound>
