sutezolid   Click here for help

GtoPdb Ligand ID: 12772

Synonyms: MMV688756 | PF-02341272 | PNU-100480 | U-100480
PDB Ligand
Compound class: Synthetic organic
Comment: Originally developed by Upjohn (later incorporated into Pfizer), sutezolid is an oxazolidinone class antibacterial with potent antimycobacterial activity [1]. It is being clinically evaluated as a treatment for tuberculosis (TB).
Sutezolid is included in the Medicines for Malaria (MMV) and Drugs for Neglected Diseases Initiative (DNDi) Pandemic Response Box.

sutezolid is commercially available from our sponsors

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 5
Topological polar surface area 87.18
Molecular weight 353.41
XLogP 1.57
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 CC(=O)NC[C@H]1CN(C2=CC=C(C(=C2)F)N3CCSCC3)C(=O)O1
Isomeric SMILES CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCSCC3)F
InChI InChI=1S/C16H20FN3O3S/c1-11(21)18-9-13-10-20(16(22)23-13)12-2-3-15(14(17)8-12)19-4-6-24-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
InChI Key FNDDDNOJWPQCBZ-ZDUSSCGKSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[[(5S)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
International Nonproprietary Names Click here for help
INN number INN
9444 sutezolid
Synonyms Click here for help
MMV688756 | PF-02341272 | PNU-100480 | U-100480
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sutezolid
Other databases
BindingDB Ligand 50560041
CAS Registry No. 168828-58-8 (source: Scifinder)
ChEMBL Ligand CHEMBL288149
DrugBank Ligand DB11905
GtoPdb PubChem SID 483123320
PubChem CID 465951
RCSB PDB Ligand 9EN
Search Google for chemical match using the InChIKey FNDDDNOJWPQCBZ-ZDUSSCGKSA-N
Search Google for chemicals with the same backbone FNDDDNOJWPQCBZ
Search PubMed clinical trials sutezolid
Search PubMed titles sutezolid
Search PubMed titles/abstracts sutezolid
UniChem Compound Search for chemical match using the InChIKey FNDDDNOJWPQCBZ-ZDUSSCGKSA-N
UniChem Connectivity Search for chemical match using the InChIKey FNDDDNOJWPQCBZ-ZDUSSCGKSA-N

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MedChemExpress
Sutezolid (links to external site)
Cat. No. HY-10392