<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 03:25:14 UTC</creation_date>
  <update_date>2026-05-14 16:24:28 UTC</update_date>
  <accession/>
  <common_name>Pravastatin</common_name>
  <class>SmallMolecule</class>
  <description>Pravastatin is an organic compound with the formula C23H36O7 and an average molecular weight of 424.53 g/mol. Pravastatin belongs to the medium-chain hydroxy acids and derivatives, a subclass of hydroxy acids and derivatives within the organic compounds. It is recorded as a biological antioxidant (PMC8252743).

The compound is identified as a lipid modifying agent within healthcare, pharmaceuticals, and veterinary products. It has two recorded protein targets, acting as an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) and Histone deacetylase 2 (HDAC2). The oral route is the recorded exposure route for this substance.

Pravastatin is found in or released from 13 recorded sources. These include drinking water and water supply (Drinking water), as well as food, food processing and cookware sources such as the preparation of malt, the preparation of wort, the preparation of wine or sparkling wine, and fermentation processes for beer. Within household cleaning and consumer products, it is associated with cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in electrical and electronic equipment, specifically antennas, amplifiers, television systems, and electrically stimulated smoking devices.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C23H36O7</chemical_formula>
  <average_molecular_weight>424.5277</average_molecular_weight>
  <monisotopic_moleculate_weight>424.246103506</monisotopic_moleculate_weight>
  <iupac_name>(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid</iupac_name>
  <traditional_iupac>pravastatin</traditional_iupac>
  <cas_registry_number>81093-37-0</cas_registry_number>
  <smiles>[H][C@]12[C@H](C[C@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(O)=O)OC(=O)[C@@H](C)CC</smiles>
  <inchi>InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1</inchi>
  <inchikey>TUZYXOIXSAXUGO-PZAWKZKUSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Fatty alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>3-hydroxy carboxylic acid</descriptor>
      <descriptor>carbobicyclic compound</descriptor>
      <descriptor>carboxylic ester</descriptor>
      <descriptor>hydroxy monocarboxylic acid</descriptor>
      <descriptor>secondary alcohol</descriptor>
      <descriptor>statin (semi-synthetic)</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Pravastatin Action Pathway</name>
      <smpdb_id>SMP0000089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pravastatin Action Pathway (New)</name>
      <smpdb_id>SMP0124576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pravastatin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142638</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.42e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5277</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.246103506</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]12[C@H](C[C@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(O)=O)OC(=O)[C@@H](C)CC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H36O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TUZYXOIXSAXUGO-PZAWKZKUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>113.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</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:0x00007f7267625a08&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00175</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>54687</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4720</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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  </targets>
</compound>
