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
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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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Click here for structure editor
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 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.

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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
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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.

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/)

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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/)
References
1. Chakraborty S, Gruber T, Barry 3rd CE, Boshoff HI, Rhee KY. (2013)
Para-aminosalicylic acid acts as an alternative substrate of folate metabolism in Mycobacterium tuberculosis.
Science, 339 (6115): 88-91. [PMID:23118010]
2. Donald PR, Diacon AH. (2015)
Para-aminosalicylic acid: the return of an old friend.
Lancet Infect Dis, 15 (9): 1091-1099. [PMID:26277036]
3. Lehmann J. (1946)
Para-aminosalicylic acid in the treatment of tuberculosis.
Lancet, 1 (6384): 15. [PMID:21008766]
4. Zheng J, Rubin EJ, Bifani P, Mathys V, Lim V, Au M, Jang J, Nam J, Dick T, Walker JR et al.. (2013)
para-Aminosalicylic acid is a prodrug targeting dihydrofolate reductase in Mycobacterium tuberculosis.
J Biol Chem, 288 (32): 23447-56. [PMID:23779105]