oxolinic acid   Click here for help

GtoPdb Ligand ID: 12999

Approved drug PDB Ligand
oxolinic acid is an approved drug
Compound class: Synthetic organic
Comment: Oxolinic acid is a quinolone antibacterial compound, with activity against Gram-negative bacteria [1].
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 CDK toolkit. 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 6
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 76.07
Molecular weight 261.23
XLogP 1.65
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCN1C=C(C(=O)C2=C1C=C3C(=C2)OCO3)C(=O)O
Isomeric SMILES CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
InChI InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
InChI Key KYGZCKSPAKDVKC-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
1866 oxolinic acid
Database Links Click here for help
CAS Registry No. 14698-29-4 (source: Scifinder)
ChEBI CHEBI:138856
ChEMBL Ligand CHEMBL416755
DrugBank Ligand DB13627
DrugCentral Ligand 2024
GtoPdb PubChem SID 485206120
PubChem CID 4628
RCSB PDB Ligand OXI
Search Google for chemical match using the InChIKey KYGZCKSPAKDVKC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KYGZCKSPAKDVKC
Search PubMed clinical trials oxolinic acid
Search PubMed titles oxolinic acid
Search PubMed titles/abstracts oxolinic acid
UniChem Compound Search for chemical match using the InChIKey KYGZCKSPAKDVKC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KYGZCKSPAKDVKC-UHFFFAOYSA-N