<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:22 UTC</creation_date>
  <update_date>2025-11-18 23:03:05 UTC</update_date>
  <accession>FDB006923</accession>
  <name>Carnosolic acid</name>
  <description>Carnosolic acid, also known as carnosolate, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Carnosolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Carnosolic acid can be found in common sage and rosemary, which makes carnosolic acid a potential biomarker for the consumption of these food products. </description>
  <synonyms>
  </synonyms>
  <chemical_formula>C20H28O5</chemical_formula>
  <average_molecular_weight>348.4333</average_molecular_weight>
  <monisotopic_moleculate_weight>348.193674006</monisotopic_moleculate_weight>
  <iupac_name>5,6,9-trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid</iupac_name>
  <traditional_iupac>5,6,9-trihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2O)C(O)=O</smiles>
  <inchi>InChI=1S/C20H28O5/c1-10(2)11-8-12-13(21)9-14-19(3,4)6-5-7-20(14,18(24)25)15(12)17(23)16(11)22/h8,10,13-14,21-23H,5-7,9H2,1-4H3,(H,24,25)</inchi>
  <inchikey>XMKKZBYHMFTMOJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.</description>
    <direct_parent>Diterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydrophenanthrenes</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Naphthalenecarboxylic acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>1-naphthalenecarboxylic acid</substituent>
      <substituent>1-naphthalenecarboxylic acid or derivatives</substituent>
      <substituent>Abietane diterpenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydrophenanthrene</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.81e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5,6,9-trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>348.4333</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>348.193674006</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H28O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H28O5/c1-10(2)11-8-12-13(21)9-14-19(3,4)6-5-7-20(14,18(24)25)15(12)17(23)16(11)22/h8,10,13-14,21-23H,5-7,9H2,1-4H3,(H,24,25)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XMKKZBYHMFTMOJ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>97.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>94.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>37.93</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</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::MsMs</type>
      <spectrum_id>54393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>54394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>54395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603463</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>
      <average_value>210.0</average_value>
      <max_value>210.0</max_value>
      <min_value>210.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Rosemary</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Rosmarinus officinalis</name_scientific>
      <ncbi_taxonomy_id>39367</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti hepatotoxic</name>
      <id>328</id>
      <definition>Any compound that is able to prevent damage to the liver.</definition>
    </health_effect>
    <health_effect>
      <name>Anti HIV</name>
      <id>333</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Anti lipoperoxidant</name>
      <id>407</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti radicular</name>
      <id>572</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>Cytotoxic</name>
      <id>859</id>
      <definition>A role played by the molecular entity or part thereof which causes the development of a pathological process.</definition>
    </health_effect>
    <health_effect>
      <name>Protease inhibitor</name>
      <id>1262</id>
      <definition>A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).</definition>
    </health_effect>
  </health_effects>
</compound>
