para-aminosalicylic acid   Click here for help

GtoPdb Ligand ID: 13652

Synonyms: 4-aminosalicylic acid | Granupas® | p-aminosalicylic acid | Paser® | Rezipas®
Approved drug PDB Ligand
para-aminosalicylic acid is an approved drug (FDA, EMA (2014))
Compound class: Synthetic organic
Comment: Para-aminosalicylic acid is a structural analogue of 4-aminobenzoic acid (pABA) with activity against mycobacteria. It was one of the first drugs to be introduced as a treatment for tuberculosis (TB) [2-3].

para-aminosalicylic acid is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 83.55
Molecular weight 153.14
XLogP 0.2
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES C1=C(C=C(C(=C1)C(=O)O)O)N
Isomeric SMILES C1=CC(=C(C=C1N)O)C(=O)O
InChI InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
InChI Key WUBBRNOQWQTFEX-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
4-amino-2-hydroxybenzoic acid
Synonyms Click here for help
4-aminosalicylic acid | Granupas® | p-aminosalicylic acid | Paser® | Rezipas®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Para-aminosalicylic acid (Rezipas)
Other databases
CAS Registry No. 65-49-6 (source: Scifinder)
ChEBI CHEBI:27565
ChEMBL Ligand CHEMBL1169
DrugBank Ligand DB00233
DrugCentral Ligand 2050
GtoPdb PubChem SID 507750286
PubChem CID 4649
RCSB PDB Ligand BHA
Search Google for chemical match using the InChIKey WUBBRNOQWQTFEX-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WUBBRNOQWQTFEX
UniChem Compound Search for chemical match using the InChIKey WUBBRNOQWQTFEX-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey WUBBRNOQWQTFEX-UHFFFAOYSA-N

Product suppliers

View disclaimer

Sponsored products disclaimer

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.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

MedChemExpress
4-Aminosalicylic acid (links to external site)
Cat. No. HY-I0447