AMINOSALICYLIC ACID

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Search structure


Trade Names	PARASAL PASER
Synonyms	4-aminosalicylic acid Aminosalicylate Aminosalicylic Acid Aminosalicylic acid Aminosalicylic acid resin complex Benzoic acid, 4-amino-2-hydroxy- Granupas NSC-2083 P-aminosalicylic acid Para-aminosalicylic acid Parasal Pas Paser Paskalium Rezipas Teebacin
Status
Molecule Category	Free-form
UNII	5B2658E0N2
EPA CompTox	DTXSID2022591


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	WUBBRNOQWQTFEX-UHFFFAOYSA-N
Smiles	Nc1ccc(C(=O)O)c(O)c1
InChI	InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C7H7NO3
Molecular Weight	153.14
AlogP	0.67
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	1.0
Polar Surface Area	83.55
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	11.0

Bioactivity

Mechanism of Action	Action	Reference
Dihydrofolate reductase inhibitor	INHIBITOR	PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	-	-	-	15
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M34 family	-	-	-	-	30
Enzyme Protease Metallo protease Metallo protease MAM clan Metallo protease M10A subfamily	-	-	-	-
Enzyme	-	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antimycobacterial activity of compound against Mycobacterium tuberculosis H37Rv at 8 ug/mL	Mycobacterium tuberculosis	92.0 %
Inhibition of mushroom tyrosinase at 1 mM after 10 mins	Agaricus bisporus	55.0 %
Inhibition of human recombinant 5-lipoxygenase at 1 mM after 10 mins by fluorescence assay	Homo sapiens	60.0 %
Inhibition of recombinant anthrax lethal factor at 1 mM after 30 mins by fluorescence assay	Bacillus anthracis	30.0 %
Inhibition of human recombinant MMP1 at 1 mM after 30 mins	Homo sapiens	-7.0 %
Inhibition of human recombinant MMP2 at 1 mM after 30 mins	Homo sapiens	-1.0 %
Inhibition of human recombinant MMP3 at 1 mM after 30 mins	Homo sapiens	4.0 %
Inhibition of human recombinant MMP8 at 1 mM after 30 mins	Homo sapiens	8.0 %
Inhibition of human recombinant MMP9 at 1 mM after 30 mins	Homo sapiens	24.0 %
Inhibition of mouse recombinant iNOS at 1 mM after 40 mins by colorimetric assay	Mus musculus	8.0 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control	Homo sapiens	33.0 %
Inhibition of Mycobacterium tuberculosis H37Rv isocitrate lyase assessed as glyoxylate phenyl hydrazone formation at 10 uM	Mycobacterium tuberculosis H37Rv	10.0 %
Inhibition of mouse recombinant glycolate oxidase expressed in Escherichia coli at 25 uM using glycolate as substrate after 1 min by sulfonated DCIP dye-based assay relative to control	Mus musculus	14.9 %
Inhibition of recombinant Mycobacterium tuberculosis H37Rv ICL1 expressed in Escherichia coli BL21 (DE3) cells at 10 uM using (+)-potassium Ds-threo-isocitrate as substrate by glyoxylate phenyl hydrazone formation assay relative to control	Mycobacterium tuberculosis H37Rv	0.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	27565
ChEMBL	CHEMBL1169
DrugBank	DB00233
DrugCentral	2050
FDA SRS	5B2658E0N2
Human Metabolome Database	HMDB0014378
KEGG	C02518
PDB	BHA
PharmGKB	PA448382
PubChem	4649
SureChEMBL	SCHEMBL2262
ZINC	ZINC000000000922

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).