<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:00 UTC</creation_date>
  <update_date>2025-11-19 00:40:11 UTC</update_date>
  <accession>FDB013958</accession>
  <name>Norambreinolide</name>
  <description>It is used to enhance the flavour of beverages and foodstuffs. Flavouring ingredient. Constituent of labdanum oil and clary sage (Salvia sclarea). Norambreinolide is found in herbs and spices.</description>
  <synonyms>
    <synonym>(+)-norambreinolide</synonym>
    <synonym>12-Norambreinolide</synonym>
    <synonym>3a,6,6,9a-Tetramethyl-decahydro-naphtho[2,1-b]furan-2-one</synonym>
    <synonym>3a,6,6,9a-Tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one</synonym>
    <synonym>Decahydrotetramethylnaphthofuranone</synonym>
    <synonym>FEMA 3794</synonym>
    <synonym>Norambreinolid</synonym>
    <synonym>Norambreinolide</synonym>
    <synonym>Norambreinolide dorm</synonym>
    <synonym>Norambreinolide, (+)-</synonym>
    <synonym>Sclareolide</synonym>
  </synonyms>
  <chemical_formula>C16H26O2</chemical_formula>
  <average_molecular_weight>250.3764</average_molecular_weight>
  <monisotopic_moleculate_weight>250.193280076</monisotopic_moleculate_weight>
  <iupac_name>3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan-2-one</iupac_name>
  <traditional_iupac>sclareolide</traditional_iupac>
  <cas_registry_number>564-20-5</cas_registry_number>
  <smiles>CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2</smiles>
  <inchi>InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3</inchi>
  <inchikey>IMKJGXCIJJXALX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon  made up of two fused benzene rings.</description>
    <direct_parent>Naphthofurans</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Naphthofurans</class>
    <sub_class/>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Gamma butyrolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Naphthofuran</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.85e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 122-125°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-7.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>250.3764</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>250.193280076</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H26O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>IMKJGXCIJJXALX-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>26.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>71.16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>29.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</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>17444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>137001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2301540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2301541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2301542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3063994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3063995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3063996</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB35293</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:0x000055ce30d5ebd0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>ambergris</name>
    </flavor>
    <flavor>
      <name>dry</name>
    </flavor>
    <flavor>
      <name>labdanum</name>
    </flavor>
    <flavor>
      <name>paper</name>
    </flavor>
    <flavor>
      <name>woody</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
