eperezolid   Click here for help

GtoPdb Ligand ID: 10803

Synonyms: comound 2 [PMID: 23584544] | PNU-100592 | PNU100592 | U-100592 | U100592
Compound class: Synthetic organic
Comment: Eperezolid is a oxazolidinone antibacterial. It inhibits protein synthesis by blocking function of the bacterial 50S ribosomal subunit. Eperezolid is not as potent as linezolid, which was the first oxazolidinone to be approved for clinical use.
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 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.

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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 102.42
Molecular weight 394.17
XLogP -0.2
No. Lipinski's rules broken 0
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.

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Canonical SMILES OCC(=O)N1CCN(CC1)c1ccc(cc1F)N1C[C@@H](OC1=O)CNC(=O)C
Isomeric SMILES OCC(=O)N1CCN(CC1)c1ccc(cc1F)N1C[C@@H](OC1=O)CNC(=O)C
InChI InChI=1S/C18H23FN4O5/c1-12(25)20-9-14-10-23(18(27)28-14)13-2-3-16(15(19)8-13)21-4-6-22(7-5-21)17(26)11-24/h2-3,8,14,24H,4-7,9-11H2,1H3,(H,20,25)/t14-/m0/s1
InChI Key SIMWTRCFFSTNMG-AWEZNQCLSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[[(5S)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
International Nonproprietary Names Click here for help
INN number INN
7585 eperezolid
Synonyms Click here for help
comound 2 [PMID: 23584544] | PNU-100592 | PNU100592 | U-100592 | U100592
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Eperezolid, PNU 100592, U 100592 | |
Other databases
CAS Registry No. 165800-04-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL47955
GtoPdb PubChem SID 405560244
PubChem CID 73214
Search Google for chemical match using the InChIKey SIMWTRCFFSTNMG-AWEZNQCLSA-N
Search Google for chemicals with the same backbone SIMWTRCFFSTNMG
Search PubMed clinical trials eperezolid
Search PubMed titles eperezolid
Search PubMed titles/abstracts eperezolid
UniChem Compound Search for chemical match using the InChIKey SIMWTRCFFSTNMG-AWEZNQCLSA-N
UniChem Connectivity Search for chemical match using the InChIKey SIMWTRCFFSTNMG-AWEZNQCLSA-N