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nitroxoline   Click here for help

GtoPdb Ligand ID: 13964

Approved drug PDB Ligand
nitroxoline is an approved drug
Compound class: Synthetic organic
Comment: Nitroxoline is an antimicrobial used to treat urinary tract infections [1]. Repurposing of nitroxoline for infectious diseases and oncological indications has been proposed, although clinical translation pharmacokinetic challenges will hamper clinical translation.
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 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 75.73
Molecular weight 190.16
XLogP 0.8
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=CN=C2C(=C1)C(=CC=C2O)[N+](=O)[O-]
Isomeric SMILES C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
InChI InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
InChI Key RJIWZDNTCBHXAL-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
5-nitroquinolin-8-ol
International Nonproprietary Names Click here for help
INN number INN
1833 nitroxoline
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nitroxoline
Other databases
CAS Registry No. 4008-48-4 (source: Scifinder)
ChEBI CHEBI:67121
ChEMBL Ligand CHEMBL1454910
DrugBank Ligand DB01422
DrugCentral Ligand 1954
PubChem CID 19910
RCSB PDB Ligand HNQ
Search Google for chemical match using the InChIKey RJIWZDNTCBHXAL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RJIWZDNTCBHXAL
Search PubMed clinical trials nitroxoline
Search PubMed titles nitroxoline
Search PubMed titles/abstracts nitroxoline
UniChem Compound Search for chemical match using the InChIKey RJIWZDNTCBHXAL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RJIWZDNTCBHXAL-UHFFFAOYSA-N