nalidixic acid   Click here for help

GtoPdb Ligand ID: 12773

Synonyms: NegGram® | Win 18,320
Approved drug PDB Ligand
nalidixic acid is an approved drug (FDA (1964), EMA)
Compound class: Synthetic organic
Comment: Nalidixic acid is a 1,8-naphthyridine derivative belonging to the quinolone class of antibacterial compounds, with activity against Gram-negative bacteria [3].

nalidixic 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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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 5
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 69.97
Molecular weight 232.24
XLogP 1
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 CCN1C=C(C(=O)C2=CC=C(C)N=C21)C(=O)O
Isomeric SMILES CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
InChI InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)
InChI Key MHWLWQUZZRMNGJ-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. FDA (1964)  |  EMA (0)
Withdrawn drug? Yes
IUPAC Name Click here for help
1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
1450 nalidixic acid
Synonyms Click here for help
NegGram® | Win 18,320
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nalidixic acid
Other databases
BindingDB Ligand 21691
CAS Registry No. 389-08-2 (source: Scifinder)
ChEBI CHEBI:100147
ChEMBL Ligand CHEMBL5
DrugBank Ligand DB00779
DrugCentral Ligand 1875
GtoPdb PubChem SID 483123321
PubChem CID 4421
RCSB PDB Ligand NIX
Search Google for chemical match using the InChIKey MHWLWQUZZRMNGJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MHWLWQUZZRMNGJ
Search PubMed clinical trials nalidixic acid
Search PubMed titles nalidixic acid
Search PubMed titles/abstracts nalidixic acid
UniChem Compound Search for chemical match using the InChIKey MHWLWQUZZRMNGJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MHWLWQUZZRMNGJ-UHFFFAOYSA-N
Wikipedia Nalidixic acid

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MedChemExpress
Nalidixic acid (links to external site)
Cat. No. HY-B0398
Nalidixic acid (Standard) (links to external site)
Cat. No. HY-B0398R