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zabofloxacin   Click here for help

GtoPdb Ligand ID: 10873

Synonyms: DW-224a
Compound class: Synthetic organic
Comment: Zabofloxacin is a fluoroquinolone antibacterial that inhibits type II and type IV topoisomerases [1]. It has activity against Gram-positive bacteria and against Gram-negative Neisseria gonorrhoeae, including strains that are resistant to other quinolone antibacterials.
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 2
Rotatable bonds 4
Topological polar surface area 109.05
Molecular weight 401.15
XLogP 3.28
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 CO/N=C\1/CN(CC21CNC2)c1nc2c(cc1F)c(=O)c(cn2C1CC1)C(=O)O
Isomeric SMILES CO/N=C\1/CN(CC21CNC2)c1nc2c(cc1F)c(=O)c(cn2C1CC1)C(=O)O
InChI InChI=1S/C19H20FN5O4/c1-29-23-14-6-24(9-19(14)7-21-8-19)17-13(20)4-11-15(26)12(18(27)28)5-25(10-2-3-10)16(11)22-17/h4-5,10,21H,2-3,6-9H2,1H3,(H,27,28)/b23-14-
InChI Key ZNPOCLHDJCAZAH-UCQKPKSFSA-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
IUPAC Name Click here for help
1-cyclopropyl-6-fluoro-7-[(8E)-8-methoxyimino-2,6-diazaspiro[3.4]octan-6-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
8594 zabofloxacin
Synonyms Click here for help
DW-224a
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Zabofloxacin
Other databases
CAS Registry No. 219680-11-2 (source: WHO INN record)
DrugBank Ligand DB12479
DrugCentral Ligand 5249
GtoPdb PubChem SID 405560314
PubChem CID 9952872
Search Google for chemical match using the InChIKey ZNPOCLHDJCAZAH-UCQKPKSFSA-N
Search Google for chemicals with the same backbone ZNPOCLHDJCAZAH
Search PubMed clinical trials zabofloxacin
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Search PubMed titles/abstracts zabofloxacin
UniChem Compound Search for chemical match using the InChIKey ZNPOCLHDJCAZAH-UCQKPKSFSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZNPOCLHDJCAZAH-UCQKPKSFSA-N