<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:15:26 UTC</creation_date>
  <update_date>2026-08-18 03:10:27 UTC</update_date>
  <accession/>
  <common_name>Miglustat</common_name>
  <class>SmallMolecule</class>
  <description>Miglustat belongs to the piperidines, a class of organoheterocyclic compounds within the organic compounds. This compound has the chemical formula $\text{C}_{10}\text{H}_{21}\text{NO}_4$ and an average molecular weight of 219.28 g/mol.

In terms of biological activity, miglustat acts as an inhibitor of the protein target ceramide glucosyltransferase (UGCG). The compound is found in or released from three recorded sources: household cleaning and consumer products (non electric simulated smoking devices), electrical and electronic equipment (electrically stimulated smoking devices), and healthcare, pharmaceuticals and veterinary products (alimentary tract and metabolism products). The recorded route of exposure for this substance is oral.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C10H21NO4</chemical_formula>
  <average_molecular_weight>219.278</average_molecular_weight>
  <monisotopic_moleculate_weight>219.147058165</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol</iupac_name>
  <traditional_iupac>miglustat</traditional_iupac>
  <cas_registry_number>72599-27-0</cas_registry_number>
  <smiles>CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO</smiles>
  <inchi>InChI=1S/C10H21NO4/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12/h7-10,12-15H,2-6H2,1H3/t7-,8+,9-,10-/m1/s1</inchi>
  <inchikey>UQRORFVVSGFNRO-UTINFBMNSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Piperidines</class>
    <sub_class/>
    <direct_parent>Piperidines</direct_parent>
    <alternate_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>piperidines</descriptor>
      <descriptor>tertiary amino compound</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Miglustat Drug Metabolism</name>
      <smpdb_id>SMP0130779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Miglustat Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142876</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.31e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>219.278</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>219.147058165</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H21NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H21NO4/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12/h7-10,12-15H,2-6H2,1H3/t7-,8+,9-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UQRORFVVSGFNRO-UTINFBMNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>84.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7226f22278&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00419</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>51634</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>46764</chemspider_id>
  <kegg_id/>
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  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
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  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
