levonadifloxacin   Click here for help

GtoPdb Ligand ID: 10757

Synonyms: (S)-(-)-nadifloxacin | WCK 771 | WCK-771 | WCK771
Compound class: Synthetic organic
Comment: Levonadifloxacin (WCK 771) is a fluoroquinolone class antibacterial [1-3]. It is being developed as a component of a combination therapy with alalevonadifloxacin. Formulated as the levonadifloxacin arginine salt for clinical administration. We show the structure of the parent molecule here.
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 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 82.77
Molecular weight 360.15
XLogP 4.39
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 OC1CCN(CC1)c1c(F)cc2c3c1CC[C@@H](n3cc(c2=O)C(=O)O)C
Isomeric SMILES OC1CCN(CC1)c1c(F)cc2c3c1CC[C@@H](n3cc(c2=O)C(=O)O)C
InChI InChI=1S/C19H21FN2O4/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21/h8-11,23H,2-7H2,1H3,(H,25,26)/t10-/m0/s1
InChI Key JYJTVFIEFKZWCJ-JTQLQIEISA-N
References
1. Bhagwat SS, McGhee P, Kosowska-Shick K, Patel MV, Appelbaum PC. (2009)
In vitro activity of the quinolone WCK 771 against recent U.S. hospital and community-acquired Staphylococcus aureus pathogens with various resistance types.
Antimicrob Agents Chemother, 53 (2): 811-3. [PMID:19029326]
2. Bhagwat SS, Mundkur LA, Gupte SV, Patel MV, Khorakiwala HF. (2006)
The anti-methicillin-resistant Staphylococcus aureus quinolone WCK 771 has potent activity against sequentially selected mutants, has a narrow mutant selection window against quinolone-resistant Staphylococcus aureus, and preferentially targets DNA gyrase.
Antimicrob Agents Chemother, 50 (11): 3568-79. [PMID:16940059]
3. Jacobs MR, Bajaksouzian S, Windau A, Appelbaum PC, Patel MV, Gupte SV, Bhagwat SS, De Souza NJ, Khorakiwala HF. (2004)
In vitro activity of the new quinolone WCK 771 against staphylococci.
Antimicrob Agents Chemother, 48 (9): 3338-42. [PMID:15328094]