<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:04 UTC</creation_date>
  <update_date>2020-05-21 16:28:43 UTC</update_date>
  <accession>BMDB0001251</accession>
  <secondary_accessions>
    <accession>BMDB01251</accession>
  </secondary_accessions>
  <name>Lanosterin</name>
  <description/>
  <synonyms>
    <synonym>(3beta)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3beta,5alpha)-4,4,14-Trimethylcholesta-8,24-dien-3-ol</synonym>
    <synonym>4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-ol</synonym>
    <synonym>(3b)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3β)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3b,5a)-4,4,14-Trimethylcholesta-8,24-dien-3-ol</synonym>
    <synonym>(3β,5α)-4,4,14-Trimethylcholesta-8,24-dien-3-ol</synonym>
    <synonym>4,4',14a-Trimethyl-5a-cholesta-8,24-dien-3b-ol</synonym>
    <synonym>4,4',14α-Trimethyl-5α-cholesta-8,24-dien-3β-ol</synonym>
    <synonym>(3 beta)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-ol</synonym>
    <synonym>(3beta,5alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-ol</synonym>
    <synonym>Botalan base 138</synonym>
    <synonym>Lanosta-8,24-dien-3-ol</synonym>
    <synonym>Lanosta-8,24-dien-3beta-ol</synonym>
    <synonym>Lanosta-8,24-dienol</synonym>
    <synonym>Lanosterol</synonym>
    <synonym>Lanster</synonym>
    <synonym>4,4,14 alpha-Trimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol</synonym>
    <synonym>Kryptosterol</synonym>
    <synonym>Lanosterin</synonym>
    <synonym>3beta-Hydroxy-lansota-8,24-dien-21-oic acid</synonym>
    <synonym>3beta-Hydroxylanosta-8,24-diene</synonym>
    <synonym>3β-Hydroxy-lansota-8,24-dien-21-oic acid</synonym>
    <synonym>3β-Hydroxylanosta-8,24-diene</synonym>
    <synonym>4,4,14alpha-Trimethylcholesta-8,24-dien-3beta-ol</synonym>
    <synonym>4,4,14α-Trimethylcholesta-8,24-dien-3β-ol</synonym>
    <synonym>5alpha-Lanosta-8,24-dien-3beta-ol</synonym>
    <synonym>5α-Lanosta-8,24-dien-3β-ol</synonym>
    <synonym>Lanosta-8,24-dien-3β-ol</synonym>
    <synonym>Lanostadien-3beta-ol</synonym>
    <synonym>Lanostadien-3β-ol</synonym>
  </synonyms>
  <chemical_formula>C30H50O</chemical_formula>
  <average_molecular_weight>426.7174</average_molecular_weight>
  <monisotopic_moleculate_weight>426.386166222</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol</iupac_name>
  <traditional_iupac>(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol</traditional_iupac>
  <cas_registry_number>79-63-0</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1</inchi>
  <inchikey>CAHGCLMLTWQZNJ-BQNIITSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>14-alpha-methylsteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>14-alpha-methylsteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-sterol</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>tetracyclic triterpenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>140.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>426.7174</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>426.386166222</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H50O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CAHGCLMLTWQZNJ-BQNIITSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>134.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</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>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>132279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>140013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>343827</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01724</kegg_id>
  <pubchem_compound_id>246983</pubchem_compound_id>
  <drugbank_id>DB03696</drugbank_id>
  <foodb_id>FDB013802</foodb_id>
  <chemspider_id>216175</chemspider_id>
  <chebi_id>16521</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>LANOSTEROL</meta_cyc_id>
  <knapsack_id>C00003657</knapsack_id>
  <wikipedia_id>Lanosterol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>38253</bigg_id>
  <metlin_id>6108</metlin_id>
  <synthesis_reference>Maienthal, Millard; Franklin, Philip J. Preparation of lanosterol from bromolanosterol. Journal of Organic Chemistry (1955), 20 1627-30.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00014</protein_accession>
      <name>Lanosterol 14-alpha demethylase</name>
      <uniprot_id>Q4PJW3</uniprot_id>
      <gene_name>CYP51A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00804</protein_accession>
      <name>Lanosterol synthase</name>
      <uniprot_id>P84466</uniprot_id>
      <gene_name>LSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02110</protein_accession>
      <name>24-dehydrocholesterol reductase</name>
      <uniprot_id>A6QR14</uniprot_id>
      <gene_name>DHCR24</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
