probenecid   Click here for help

GtoPdb Ligand ID: 4357

Synonyms: Probalan®
Approved drug PDB Ligand
probenecid is an approved drug (FDA (1951))
Compound class: Synthetic organic
Comment: Probenecid is considered to be the prototypical uricosuric agent.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 83.06
Molecular weight 285.1
XLogP 2.29
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCN(S(=O)(=O)c1ccc(cc1)C(=O)O)CCC
Isomeric SMILES CCCN(S(=O)(=O)c1ccc(cc1)C(=O)O)CCC
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 Key DBABZHXKTCFAPX-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1951))
IUPAC Name Click here for help
4-(Dipropylsulfamoyl)benzoic acid
International Nonproprietary Names Click here for help
INN number INN
563 probenecid
Synonyms Click here for help
Probalan®
Database Links Click here for help
Specialist databases
GPCRdb Ligand probenecid
Other databases
BindingDB Ligand 50206509
CAS Registry No. 57-66-9 (source: Scifinder)
ChEMBL Ligand CHEMBL897
DrugBank Ligand DB01032
DrugCentral Ligand 2268
GtoPdb PubChem SID 178101174
PubChem CID 4911
RCSB PDB Ligand RTO
Search Google for chemical match using the InChIKey DBABZHXKTCFAPX-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DBABZHXKTCFAPX
Search PubMed clinical trials probenecid
Search PubMed titles probenecid
Search PubMed titles/abstracts probenecid
UniChem Compound Search for chemical match using the InChIKey DBABZHXKTCFAPX-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DBABZHXKTCFAPX-UHFFFAOYSA-N
Wikipedia Probenecid

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

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Tocris
Probenecid (links to external site)
Cat. No. 4107