<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:32:08 UTC</creation_date>
  <update_date>2015-07-21 06:57:47 UTC</update_date>
  <accession>FDB023595</accession>
  <name>Rabeprazole</name>
  <description>Rabeprazole is a proton pump inhibitor sold (as its sodium salt) under the brand names Aciphex and Pariet (distributed by Janssen-Cilag); Rabeprazole is a proton pump inhibitor sold (as its sodium salt) and it is used in the treatment of gastric ulcers and GERD (or heartburn). It is taken once a day along with a full glass of water (preferable 30 min before breakfast). [HMDB]</description>
  <synonyms>
    <synonym>Aciphex</synonym>
    <synonym>Clofezone</synonym>
    <synonym>Habeprazole</synonym>
    <synonym>Pariet</synonym>
    <synonym>Pariets</synonym>
    <synonym>Rabeprazole sodium</synonym>
    <synonym>Sodium rabeprazole</synonym>
  </synonyms>
  <chemical_formula>C18H21N3O3S</chemical_formula>
  <average_molecular_weight>359.443</average_molecular_weight>
  <monisotopic_moleculate_weight>359.130362243</monisotopic_moleculate_weight>
  <iupac_name>2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole</iupac_name>
  <traditional_iupac>rabeprazole</traditional_iupac>
  <cas_registry_number>117976-89-3</cas_registry_number>
  <smiles>COCCCOC1=C(C)C(CS(=O)C2=NC3=CC=CC=C3N2)=NC=C1</smiles>
  <inchi>InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)</inchi>
  <inchikey>YREYEVIYCVEVJK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.</description>
    <direct_parent>Sulfinylbenzimidazoles</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzimidazoles</class>
    <sub_class>Sulfinylbenzimidazoles</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfinyl compounds</alternative_parent>
      <alternative_parent>Sulfoxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Sulfinyl compound</substituent>
      <substituent>Sulfinylbenzimidazole</substituent>
      <substituent>Sulfoxide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>benzimidazoles</external_descriptor>
      <external_descriptor>pyridines</external_descriptor>
      <external_descriptor>sulfoxide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.36e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>4.24</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>359.443</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>359.130362243</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COCCCOC1=C(C)C(CS(=O)C2=NC3=CC=CC=C3N2)=NC=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H21N3O3S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>YREYEVIYCVEVJK-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>77.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>98.07</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>39.64</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>117487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>172516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2464206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2464207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2464208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2500745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2500746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2500747</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB05026</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>8769</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Potassium-transporting ATPase alpha chain 1</name>
      <uniprot_id>P20648</uniprot_id>
      <uniprot_name/>
      <gene_name>ATP4A</gene_name>
    </enzyme>
    <enzyme>
      <name>Potassium-transporting ATPase subunit beta</name>
      <uniprot_id>P51164</uniprot_id>
      <uniprot_name/>
      <gene_name>ATP4B</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
