danofloxacin   Click here for help

GtoPdb Ligand ID: 13667

Synonyms: Advocid® (veterinary) | Advocin® (veterinary) | CP-76,136
Compound class: Synthetic organic
Comment: Danofloxacin is a fluoroquinolone antibacterial compound, with broad-spectrum activity against both Gram-positive and Gram-negative bacteria [1-2]. It was developed for use in veterinary medicine.

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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 6
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 64.09
Molecular weight 357.38
XLogP 2.27
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 CN1C[C@@H]2C[C@H]1CN2C3=CC4=C(C=C3F)C(=O)C(=CN4C5CC5)C(=O)O
Isomeric SMILES CN1C[C@@H]2C[C@H]1CN2C3=C(C=C4C(=C3)N(C=C(C4=O)C(=O)O)C5CC5)F
InChI InChI=1S/C19H20FN3O3/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26)/t11-,12-/m0/s1
InChI Key QMLVECGLEOSESV-RYUDHWBXSA-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/)
References
1. Giles CJ, Magonigle RA, Grimshaw WT, Tanner AC, Risk JE, Lynch MJ, Rice JR. (1991)
Clinical pharmacokinetics of parenterally administered danofloxacin in cattle.
J Vet Pharmacol Ther, 14 (4): 400-10. [PMID:1663562]
2. McGuirk PR, Jefson MR, Mann DD, Elliott NC, Chang P, Cisek EP, Cornell CP, Gootz TD, Haskell SL, Hindahl MS et al.. (1992)
Synthesis and structure-activity relationships of 7-diazabicycloalkylquinolones, including danofloxacin, a new quinolone antibacterial agent for veterinary medicine.
J Med Chem, 35 (4): 611-20. [PMID:1311762]