DuP-721   Click here for help

GtoPdb Ligand ID: 10960

Synonyms: DuP 721
Compound class: Synthetic organic
Comment: DuP-721 is an oxazolidinone antibacterial with Gram-positive and Gram-negative activity [1,3]. It was developed for activity against Staphylococcus aureus, and has equal activity against methicillin-sensitive and methicillin-resistant strains [2].
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 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 75.71
Molecular weight 276.11
XLogP 0.79
No. Lipinski's rules broken 0
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 CC(=O)NCC1CN(C(=O)O1)c1ccc(cc1)C(=O)C
Isomeric SMILES CC(=O)NCC1CN(C(=O)O1)c1ccc(cc1)C(=O)C
InChI InChI=1S/C14H16N2O4/c1-9(17)11-3-5-12(6-4-11)16-8-13(20-14(16)19)7-15-10(2)18/h3-6,13H,7-8H2,1-2H3,(H,15,18)
InChI Key POXUJOYUVLWPQN-UHFFFAOYSA-N
References
1. Ashtekar DR, Costa-Periera R, Shrinivasan T, Iyyer R, Vishvanathan N, Rittel W. (1991)
Oxazolidinones, a new class of synthetic antituberculosis agent. In vitro and in vivo activities of DuP-721 against Mycobacterium tuberculosis.
Diagn Microbiol Infect Dis, 14 (6): 465-71. [PMID:1802533]
2. Maple PA, Hamilton-Miller JM, Brumfitt W. (1989)
Comparative in-vitro activity of vancomycin, teicoplanin, ramoplanin (formerly A16686), paldimycin, DuP 721 and DuP 105 against methicillin and gentamicin resistant Staphylococcus aureus.
J Antimicrob Chemother, 23 (4): 517-25. [PMID:2526111]
3. Mini E, Novelli A, Mazzei T, Periti P. (1989)
Comparative in vitro activity of the new oxazolidinones DuP 721 and DuP 105 against staphylococci and streptococci.
Eur J Clin Microbiol Infect Dis, 8 (3): 256-60. [PMID:2523807]