cefquinome   Click here for help

GtoPdb Ligand ID: 13622

Synonyms: Cobactan® (veterinary) | HR 111V
Compound class: Synthetic organic
Comment: Cefquinome is a fourth generation cephalosporin belonging to the β-lactam class of antibacterial compounds [1].
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 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.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 203.12
Molecular weight 528.61
XLogP -1.76
No. Lipinski's rules broken 1

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
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.

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/)

✖
Canonical SMILES CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@@H]2C(=O)N3C(=C(C[N+]4=C5CCCCC5=CC=C4)CS[C@H]23)C(=O)[O-]
Isomeric SMILES CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCCC5)C(=O)[O-]
InChI InChI=1S/C23H24N6O5S2/c1-34-27-16(14-11-36-23(24)25-14)19(30)26-17-20(31)29-18(22(32)33)13(10-35-21(17)29)9-28-8-4-6-12-5-2-3-7-15(12)28/h4,6,8,11,17,21H,2-3,5,7,9-10H2,1H3,(H3-,24,25,26,30,32,33)/b27-16-/t17-,21-/m1/s1
InChI Key YWKJNRNSJKEFMK-PQFQYKRASA-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/)
Bioactivity Comments
Cefquinome demonstrates broad-spectrum antibacterial activity against Gram-positive and Gram-negative bacteria. The MIC for activity in vitro against methicillin-susceptible and -resistant Staphylococcus aureus is in the range of 0.195-0.25 and 1.563-50 μg/ml respectively, against Streptococcus spp. it is ≤0.006-0.781 μg/ml, against Escherichia coli it is ≤0.006-0.781 μg/ml, and against Salmonella spp. it is 0.049-0.391 μg/ml (further in vitro data are reported in [1]). Cefquinome is resistant to inactivation by common β-lactamases with the exception of OXA-1 [1].