<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:29 UTC</creation_date>
  <update_date>2025-11-19 00:49:57 UTC</update_date>
  <accession>FDB014824</accession>
  <name>Physcion</name>
  <description>Physcion, also known as emodin monomethyl ether or parienin, is a member of the class of compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Physcion is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Physcion can be synthesized from 2-methylanthraquinone. Physcion can also be synthesized into torososide B and physcion 8-gentiobioside. Physcion can be found in common sage, garden rhubarb, and sorrel, which makes physcion a potential biomarker for the consumption of these food products. Physcion has also been shown to protect lichens against UV-B light, at high altitudes in Alpine regions. The UV-B light stimulates production of parietin and the parietin protects the lichens from damage. Lichens in arctic regions such as Svarlbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of Ozone layer thinning .</description>
  <synonyms>
    <synonym>1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione</synonym>
    <synonym>1,8-Dihydroxy-3-methoxy-6-methyl-anthraquinone</synonym>
    <synonym>1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione</synonym>
    <synonym>1,8-Dihydroxy-3-methoxy-6-methylanthraquinone</synonym>
    <synonym>1,8-Dihydroxy-3-methyl-6-methoxy-9,10-anthraquinone</synonym>
    <synonym>9, 10-Anthracenedione, 1,8-dihydroxy-3-methoxy-6-methyl-</synonym>
    <synonym>9,10-Anthracenedione, 1,8-dihydroxy-3-methoxy-6-methyl-</synonym>
    <synonym>Anthraquinone, 1,8-dihydroxy-3-methoxy-6-methyl-</synonym>
    <synonym>Emodin 3-methyl ether</synonym>
    <synonym>Emodin-3-methyl ether</synonym>
    <synonym>Methoxyemodin</synonym>
    <synonym>Methylemodin</synonym>
    <synonym>Parietin</synonym>
    <synonym>Physcic acid</synonym>
    <synonym>Physcion</synonym>
    <synonym>Physcion (senna)</synonym>
    <synonym>Physcione</synonym>
    <synonym>Przewalskinone B</synonym>
    <synonym>Rheochrysidin</synonym>
  </synonyms>
  <chemical_formula>C16H12O5</chemical_formula>
  <average_molecular_weight>284.2635</average_molecular_weight>
  <monisotopic_moleculate_weight>284.068473494</monisotopic_moleculate_weight>
  <iupac_name>1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione</iupac_name>
  <traditional_iupac>physcion</traditional_iupac>
  <cas_registry_number>521-61-9</cas_registry_number>
  <smiles>COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)C2=O</smiles>
  <inchi>InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3</inchi>
  <inchikey>FFWOKTFYGVYKIR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.</description>
    <direct_parent>Anthraquinones</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Anthracenes</class>
    <sub_class>Anthraquinones</sub_class>
    <molecular_framework>Aromatic homopolycyclic 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>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aryl ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>9,10-anthraquinone</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Anthraquinone</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Anthraquinone type</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.67e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 209-210°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.97</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>7.89</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>284.2635</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>284.068473494</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)C2=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H12O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FFWOKTFYGVYKIR-UHFFFAOYSA-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>76.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>28.69</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</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>83535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158459</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Common sage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Salvia officinalis</name_scientific>
      <ncbi_taxonomy_id>38868</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden rhubarb</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rheum rhabarbarum</name_scientific>
      <ncbi_taxonomy_id>3621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sorrel</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rumex acetosa</name_scientific>
      <ncbi_taxonomy_id>41241</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <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>Calcium antagonist</name>
      <id>748</id>
      <definition>Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.</definition>
    </health_effect>
    <health_effect>
      <name>Cathartic</name>
      <id>784</id>
      <definition>Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.</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>Purgative</name>
      <id>1275</id>
      <definition>An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.</definition>
    </health_effect>
  </health_effects>
</compound>
