<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:56:58 UTC</creation_date>
  <update_date>2026-08-21 21:21:09 UTC</update_date>
  <accession/>
  <common_name>Tadalafil</common_name>
  <class>SmallMolecule</class>
  <description>Tadalafil is an organic compound with the formula C22H19N3O4 and an average molecular weight of 389.40 g/mol. Tadalafil belongs to the pyridoindoles, a subclass of indoles and derivatives within the organic compounds. It is classified as an organoheterocyclic compound.

The substance has three recorded protein targets, acting as an inhibitor of cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A), as well as targeting dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A (PDE11A) and retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma (PDE6G). Regarding health effects, it is associated with a decrease in hypotension (PMC12454544).

Tadalafil is found in or released from 35 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used in urologicals, antihypertensives, and drugs used in benign prostatic hypertrophy. Other sources include building and construction materials such as floors, ceilings, roofs, fencing, and stairs and ramps. It is also associated with food, food processing, and cookware, specifically the treatment of hops and the processing of meats and fish, as well as the preparation of sparkling wine or wine. Household cleaning and consumer products include pipe accessories, tobacco pipes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including antennas, coils, discharge lamps, amplifiers, and colour television systems. The recorded exposure route for this compound is oral.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C22H19N3O4</chemical_formula>
  <average_molecular_weight>389.404</average_molecular_weight>
  <monisotopic_moleculate_weight>389.137556111</monisotopic_moleculate_weight>
  <iupac_name>(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),11,13,15-tetraene-4,7-dione</iupac_name>
  <traditional_iupac>tadalafil</traditional_iupac>
  <cas_registry_number>171596-29-5</cas_registry_number>
  <smiles>[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1</smiles>
  <inchi>InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1</inchi>
  <inchikey>WOXKDUGGOYFFRN-IIBYNOLFSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Pyridoindoles</sub_class>
    <direct_parent>Beta carbolines</direct_parent>
    <alternate_parents>
      <alternative_parent>2,5-dioxopiperazines</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alpha amino acids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Benzodioxoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-methylpiperazines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrroles</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,4-diazinane</substituent>
      <substituent>2,5-dioxopiperazine</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzodioxole</substituent>
      <substituent>Beta-carboline</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dioxopiperazine</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-alkylpiperazine</substituent>
      <substituent>N-methylpiperazine</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>Oxacycle</substituent>
      <substituent>Piperazine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>benzodioxoles</descriptor>
      <descriptor>pyrazinopyridoindole</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Tadalafil Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143258</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.64</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.50e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),11,13,15-tetraene-4,7-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>389.404</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>389.137556111</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C22H19N3O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WOXKDUGGOYFFRN-IIBYNOLFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>104.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf32c9760&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00820</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>110635</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>99301</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>
