cetefloxacin   Click here for help

GtoPdb Ligand ID: 10790

Synonyms: compound 43f [PMID: 7990118] | E-4868 | E4868
Compound class: Synthetic organic
Comment: Cetefloxacin is a fluoroquinolone class antibacterial [2-4].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 88.04
Molecular weight 403.11
XLogP 5.29
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES Fc1ccc(c(c1)F)n1cc(C(=O)O)c(=O)c2c1cc(c(c2)F)N1C[C@H]([C@@H]1C)N
Isomeric SMILES Fc1ccc(c(c1)F)n1cc(C(=O)O)c(=O)c2c1cc(c(c2)F)N1C[C@H]([C@@H]1C)N
InChI InChI=1S/C20H16F3N3O3/c1-9-15(24)8-25(9)18-6-17-11(5-14(18)23)19(27)12(20(28)29)7-26(17)16-3-2-10(21)4-13(16)22/h2-7,9,15H,8,24H2,1H3,(H,28,29)/t9-,15+/m0/s1
InChI Key LTDOHCZUKCZDEQ-BJOHPYRUSA-N
References
1. Frigola J, Torrens A, Castrillo JA, Mas J, Vañó D, Berrocal JM, Calvet C, Salgado L, Redondo J, García-Granda S et al.. (1994)
7-azetidinylquinolones as antibacterial agents. 2. Synthesis and biological activity of 7-(2,3-disubstituted-1-azetidinyl)-4-oxoquinoline- and -1,8-naphthyridine-3-carboxylic acids. Properties and structure-activity relationships of quinolones with an azetidine moiety.
J Med Chem, 37 (24): 4195-210. [PMID:7990118]
2. Guinea J, Robert M, Gargallo-Viola D, Xicota MA, Garcia J, Tudela E, Esteve M, Coll R, Pares M, Roser R. (1993)
In vitro and in vivo antibacterial activities of E-4868, a new fluoroquinolone with a 7-azetidin ring substituent.
Antimicrob Agents Chemother, 37 (4): 868-74. [PMID:8388202]
3. Mirelis B, Navarro F, Miró E, Coll R, Xicota MA, Prats G. (1995)
In vitro activity of E-4868, a new fluoroquinolone with a 7-azetidin ring, compared with ciprofloxacin, ofloxacin and fleroxacin.
Drugs Exp Clin Res, 21 (4): 129-38. [PMID:8529525]
4. Murray PR, Jones RN, Washington JA, Gerlach EH, Allen SD. (1993)
In vitro comparison of E4868, a new trifluoroquinolone, with ciprofloxacin and temafloxacin tested against 5192 recent clinical isolates from five medical centers.
Diagn Microbiol Infect Dis, 17 (4): 307-11. [PMID:8112046]