enoxacin   Click here for help

GtoPdb Ligand ID: 8882

Synonyms: AT-2266 | CI-919 | Penetrex®
Approved drug
enoxacin is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Enoxacin was developed as a oral broad-spectrum fluoroquinolone antibacterial for the treatment of urinary tract infections and gonorrhea.
Enoxacin has been reported as an inhibitor of the interaction between the B2 subunit of vacuolar H+-ATPase (ATP6V1B2) and microfilaments [2], an interaction required for translocation of the ATPase to the plasma membrane. This process effects activation of osteoclasts and regulates bone resorption, making this interaction a novel target for pharmaceutical intervention to reduce the pathologies associated with bone-loss condtions [3].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 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 2
Rotatable bonds 3
Topological polar surface area 87.46
Molecular weight 320.13
XLogP 3.57
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 CCn1cc(C(=O)O)c(=O)c2c1nc(N1CCNCC1)c(c2)F
Isomeric SMILES CCn1cc(C(=O)O)c(=O)c2c1nc(N1CCNCC1)c(c2)F
InChI InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
InChI Key IDYZIJYBMGIQMJ-UHFFFAOYSA-N
References
1. Emde A, Eitan C, Liou LL, Libby RT, Rivkin N, Magen I, Reichenstein I, Oppenheim H, Eilam R, Silvestroni A et al.. (2015)
Dysregulated miRNA biogenesis downstream of cellular stress and ALS-causing mutations: a new mechanism for ALS.
EMBO J, 34 (21): 2633-51. [PMID:26330466]
2. Ostrov DA, Magis AT, Wronski TJ, Chan EK, Toro EJ, Donatelli RE, Sajek K, Haroun IN, Nagib MI, Piedrahita A et al.. (2009)
Identification of enoxacin as an inhibitor of osteoclast formation and bone resorption by structure-based virtual screening.
J Med Chem, 52 (16): 5144-51. [PMID:19630402]
3. Qin A, Cheng TS, Pavlos NJ, Lin Z, Dai KR, Zheng MH. (2012)
V-ATPases in osteoclasts: structure, function and potential inhibitors of bone resorption.
Int J Biochem Cell Biol, 44 (9): 1422-35. [PMID:22652318]
4. Valdez G, Heyer MP, Feng G, Sanes JR. (2014)
The role of muscle microRNAs in repairing the neuromuscular junction.
PLoS ONE, 9 (3): e93140. [PMID:24664281]