<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:30:21 UTC</creation_date>
  <update_date>2026-08-19 01:53:31 UTC</update_date>
  <accession/>
  <common_name>Probenecid</common_name>
  <class>SmallMolecule</class>
  <description>Probenecid (C13H19NO4S) is a compound with an average molecular weight of 285.36 g/mol. Probenecid belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. It is utilized as a treatment for hyperuricemia (PMC10346988).

The compound is found in or released from 45 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antigout preparations and gynecologicals. It is also recorded in building and construction materials such as floors and ceilings, household items including coins, and food, food processing, and cookware categories including food preservation, processing meats, processing fish, preparation of wort, and fermentation processes for beer. Additionally, it is found in household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, other smoking requisites, non electric simulated smoking devices, and cigar cigarettes. It is further linked to electrical and electronic equipment, including antennas, amplifiers, communication cables or conductors, colour television systems, auxiliary devices, and 23 other sources.

The recorded exposure route for probenecid is oral. The compound interacts with five recorded protein targets, acting as an antagonist, inhibitor, or inhibitory allosteric modulator of pannexin-1 (PANX1), organic anion transporter 3 (SLC22A8), solute carrier family 22 member 6 (SLC22A6), solute carrier family 22 member 11 (SLC22A11), and one other protein.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>4-(dipropylsulfamoyl)benzoic acid</synonym>
  </synonyms>
  <chemical_formula>C13H19NO4S</chemical_formula>
  <average_molecular_weight>285.359</average_molecular_weight>
  <monisotopic_moleculate_weight>285.103478791</monisotopic_moleculate_weight>
  <iupac_name>4-(dipropylsulfamoyl)benzoic acid</iupac_name>
  <traditional_iupac>probenecid</traditional_iupac>
  <cas_registry_number>57-66-9</cas_registry_number>
  <smiles>CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)</inchi>
  <inchikey>DBABZHXKTCFAPX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzenesulfonamides</sub_class>
    <direct_parent>Benzenesulfonamides</direct_parent>
    <alternate_parents>
      <alternative_parent>Aminosulfonyl compounds</alternative_parent>
      <alternative_parent>Benzenesulfonyl compounds</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonamides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aminosulfonyl compound</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenesulfonamide</substituent>
      <substituent>Benzenesulfonyl group</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid amide</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Sulfonyl</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>benzoic acids</descriptor>
      <descriptor>sulfonamide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Probenecid Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143461</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.44</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.25e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(dipropylsulfamoyl)benzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>285.359</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>285.103478791</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H19NO4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DBABZHXKTCFAPX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</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>-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:0x00007f727f030d38&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01032</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4911</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4742</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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  </targets>
</compound>
