<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:20:46 UTC</creation_date>
  <update_date>2026-05-14 16:40:21 UTC</update_date>
  <accession/>
  <common_name>Fosinopril</common_name>
  <class>SmallMolecule</class>
  <description>Fosinopril is an organic compound with the chemical formula C30H46NO7P. Fosinopril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 563.66 g/mol, Fosinopril is a heavy molecule.

This compound acts as an inhibitor of the protein target Angiotensin-converting enzyme (ACE). It is utilized within healthcare, pharmaceuticals, and veterinary products as an ACE inhibitor. Fosinopril is also found in or released from electrical and electronic equipment, specifically antennas, still video cameras, and electrically stimulated smoking devices. The recorded route of exposure for this substance is oral.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C30H46NO7P</chemical_formula>
  <average_molecular_weight>563.6625</average_molecular_weight>
  <monisotopic_moleculate_weight>563.301189343</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>fosinopril</traditional_iupac>
  <cas_registry_number>98048-97-6</cas_registry_number>
  <smiles>CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C</smiles>
  <inchi>InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39?/m1/s1</inchi>
  <inchikey>BIDNLKIUORFRQP-FKDWWROVSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Proline and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</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>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-acylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphinic acid esters</alternative_parent>
      <alternative_parent>Pyrrolidine carboxylic acids</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-acylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organophosphorus compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphinic acid ester</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>L-proline derivative</descriptor>
      <descriptor>phosphinic ester</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Fosinopril Action Pathway</name>
      <smpdb_id>SMP0000149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fosinopril Metabolism Pathway</name>
      <smpdb_id>SMP0000594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fosinopril ACE Inhibitor Action Pathway</name>
      <smpdb_id>SMP0123090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fosinopril Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142946</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>5.62</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.01e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>563.6625</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>563.301189343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H46NO7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BIDNLKIUORFRQP-FKDWWROVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>149.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>61.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</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>-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:0x00007f7221efc320&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00492</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>55891</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>50469</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
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    <target>
      <target_id>BE0000221</target_id>
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  </targets>
</compound>
