<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:13 UTC</creation_date>
  <update_date>2020-06-04 22:59:16 UTC</update_date>
  <accession>BMDB0000067</accession>
  <secondary_accessions>
    <accession>BMDB00067</accession>
  </secondary_accessions>
  <name>Cholesterol</name>
  <description>Cholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesterol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(3beta,14beta,17alpha)-Cholest-5-en-3-ol</synonym>
    <synonym>Cholest-5-en-3beta-ol</synonym>
    <synonym>Cholesterin</synonym>
    <synonym>(3b,14b,17a)-Cholest-5-en-3-ol</synonym>
    <synonym>(3Β,14β,17α)-cholest-5-en-3-ol</synonym>
    <synonym>Cholest-5-en-3b-ol</synonym>
    <synonym>Cholest-5-en-3β-ol</synonym>
    <synonym>(3Β)-cholest-5-en-3-ol</synonym>
    <synonym>(3beta)-Cholest-5-en-3-ol</synonym>
    <synonym>3Β-hydroxycholest-5-ene</synonym>
    <synonym>3beta-Hydroxycholest-5-ene</synonym>
    <synonym>5:6-Cholesten-3β-ol</synonym>
    <synonym>5:6-Cholesten-3beta-ol</synonym>
    <synonym>(-)-Cholesterol</synonym>
    <synonym>Cholesterine</synonym>
    <synonym>Cholesterol base H</synonym>
    <synonym>Cholesteryl alcohol</synonym>
    <synonym>Cholestrin</synonym>
    <synonym>Cholestrol</synonym>
    <synonym>Cordulan</synonym>
    <synonym>Dastar</synonym>
    <synonym>Dusoline</synonym>
    <synonym>Dusoran</synonym>
    <synonym>Dythol</synonym>
    <synonym>Fancol CH</synonym>
    <synonym>Hydrocerin</synonym>
    <synonym>Kathro</synonym>
    <synonym>Lanol</synonym>
    <synonym>Super hartolan</synonym>
    <synonym>Tegolan</synonym>
    <synonym>Cholesterol</synonym>
    <synonym>delta5-Cholesten-3beta-ol</synonym>
    <synonym>Δ5-Cholesten-3β-ol</synonym>
  </synonyms>
  <chemical_formula>C27H46O</chemical_formula>
  <average_molecular_weight>386.6535</average_molecular_weight>
  <monisotopic_moleculate_weight>386.354866094</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</iupac_name>
  <traditional_iupac>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</traditional_iupac>
  <cas_registry_number>57-88-5</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>HVYWMOMLDIMFJA-DPAQBDIFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-sterol</external_descriptor>
      <external_descriptor>Cholestane and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>cholestane</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>386.6535</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>386.354866094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HVYWMOMLDIMFJA-DPAQBDIFSA-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>120.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>34576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1049528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3012293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3012294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3012295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>337787</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>All Tissues</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3341.493 +/- 370.616</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Spectrometry (Autoanalyzer/BT3000 Plus)</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3290</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>775.888</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>5560534.173</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1200 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4189797.842</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>400 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4138071.943</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>800 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>5431219.425</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>No pomegranate peel extract added</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform.</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951.</reference_text>
          <pubmed_id>31873721</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform.</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951.</reference_text>
          <pubmed_id>31873721</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows</comment>
      <references>
        <reference>
          <reference_text>Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019.</reference_text>
          <pubmed_id>31867104</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Mammary Gland</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform.</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951.</reference_text>
          <pubmed_id>31873721</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Mammary Gland</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform.</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951.</reference_text>
          <pubmed_id>31873721</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>129.315</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>103.452</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>103.452</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>129.315</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>155.178</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>155.178</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>77.589</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>89.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>77.589</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>258.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>258.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>101.383</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>defatted milk/saponified</comment>
      <references>
        <reference>
          <reference_text>Shi Y, Zhang JH, Shi D, Jiang M, Zhu YX, Mei SR, Zhou YK, Dai K, Lu B: Selective solid-phase extraction of cholesterol using molecularly imprinted polymers and its application in different biological samples. J Pharm Biomed Anal. 2006 Nov 16;42(5):549-55. doi: 10.1016/j.jpba.2006.05.022. Epub 2006 Jul 21.</reference_text>
          <pubmed_id>16859856</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Placenta</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Prostate Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Ruminal Fluid</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was authenticated by external standard reference(s).</comment>
      <references>
        <reference>
          <reference_text>Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018.</reference_text>
          <pubmed_id>29634739</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Identified in bull spermatozoa by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Menezes EB, Velho ALC, Santos F, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Uncovering sperm metabolome to discover biomarkers for bull fertility. BMC Genomics. 2019 Sep 18;20(1):714. doi: 10.1186/s12864-019-6074-6.</reference_text>
          <pubmed_id>31533629</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00187</kegg_id>
  <drugbank_id>DB04540</drugbank_id>
  <foodb_id>FDB013269</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>5997</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16113</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00003648</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Cholesterol</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id>CHOLESTEROL</meta_cyc_id>
  <synthesis_reference>Zhu, Yongming; Qin, Liena; Liu, Rui.  Simple method for synthesis cholesterol from Diosgenin.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2006),  9 pp. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Shi Y, Zhang JH, Shi D, Jiang M, Zhu YX, Mei SR, Zhou YK, Dai K, Lu B: Selective solid-phase extraction of cholesterol using molecularly imprinted polymers and its application in different biological samples. J Pharm Biomed Anal. 2006 Nov 16;42(5):549-55. doi: 10.1016/j.jpba.2006.05.022. Epub 2006 Jul 21.</reference_text>
      <pubmed_id>16859856</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00016</protein_accession>
      <name>Cytochrome P450 3A28</name>
      <uniprot_id>P79102</uniprot_id>
      <gene_name>CYP3A28</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00024</protein_accession>
      <name>Prostacyclin synthase</name>
      <uniprot_id>Q29626</uniprot_id>
      <gene_name>PTGIS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00053</protein_accession>
      <name>Cholesterol side-chain cleavage enzyme, mitochondrial</name>
      <uniprot_id>P00189</uniprot_id>
      <gene_name>CYP11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00910</protein_accession>
      <name>7-dehydrocholesterol reductase</name>
      <uniprot_id>Q5E9J5</uniprot_id>
      <gene_name>DHCR7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01333</protein_accession>
      <name>EBP cholestenol delta-isomerase</name>
      <uniprot_id>Q3ZBT8</uniprot_id>
      <gene_name>EBP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01500</protein_accession>
      <name>Translocator protein</name>
      <uniprot_id>P30535</uniprot_id>
      <gene_name>TSPO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01586</protein_accession>
      <name>Bile acid receptor</name>
      <uniprot_id>Q3SZL0</uniprot_id>
      <gene_name>NR1H4</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>
      <protein_accession>BMDBP02125</protein_accession>
      <name>Apolipoprotein A-I</name>
      <uniprot_id>P15497</uniprot_id>
      <gene_name>APOA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02126</protein_accession>
      <name>SCARB1 protein</name>
      <uniprot_id>A4IFC6</uniprot_id>
      <gene_name>SCARB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02127</protein_accession>
      <name>Cystic fibrosis transmembrane conductance regulator</name>
      <uniprot_id>Q9TSX2</uniprot_id>
      <gene_name>CFTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02128</protein_accession>
      <name>Sterol regulatory element-binding protein cleavage-activating protein</name>
      <uniprot_id>A6QM06</uniprot_id>
      <gene_name>SCAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02129</protein_accession>
      <name>StAR-related lipid transfer protein 5</name>
      <uniprot_id>A1A4M6</uniprot_id>
      <gene_name>STARD5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02130</protein_accession>
      <name>APOM protein</name>
      <uniprot_id>Q3ZBQ9</uniprot_id>
      <gene_name>APOM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02131</protein_accession>
      <name>Steroidogenic acute regulatory protein, mitochondrial</name>
      <uniprot_id>Q28918</uniprot_id>
      <gene_name>STAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02132</protein_accession>
      <name>Apolipoprotein E</name>
      <uniprot_id>Q0ZCB4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02133</protein_accession>
      <name>Apolipoprotein E</name>
      <uniprot_id>A7YWR0</uniprot_id>
      <gene_name>APOE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02134</protein_accession>
      <name>Scavenger receptor class B member 1</name>
      <uniprot_id>O18824</uniprot_id>
      <gene_name>SCARB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02135</protein_accession>
      <name>Na(+)/H(+) exchange regulatory cofactor NHE-RF3</name>
      <uniprot_id>Q3T0X8</uniprot_id>
      <gene_name>PDZK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02926</protein_accession>
      <name>Gastric triacylglycerol lipase</name>
      <uniprot_id>Q29458</uniprot_id>
      <gene_name>LIPF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
