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posizolid   Click here for help

GtoPdb Ligand ID: 12762

Synonyms: AZD2563 | AZD5847
Compound class: Synthetic organic
Comment: Posizolid (AZD2563 or AZD5847) is an oxazolidinone class antibacterial with activity against Gram-positive bacteria [5]. It has antimycobacterial activity [2] and was being developed by AstraZeneca as a potential therapeutic for tuberculosis (TB).
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 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 121.13
Molecular weight 465.4
XLogP -0.24
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 C1=C(CCN(C1)C(=O)[C@H](CO)O)C2=C(C=C(C=C2F)N3C[C@H](COC4=NOC=C4)OC3=O)F
Isomeric SMILES C1CN(CC=C1C2=C(C=C(C=C2F)N3C[C@@H](OC3=O)COC4=NOC=C4)F)C(=O)[C@H](CO)O
InChI InChI=1S/C21H21F2N3O7/c22-15-7-13(26-9-14(33-21(26)30)11-31-18-3-6-32-24-18)8-16(23)19(15)12-1-4-25(5-2-12)20(29)17(28)10-27/h1,3,6-8,14,17,27-28H,2,4-5,9-11H2/t14-,17+/m1/s1
InChI Key HBUJYEUPIIJJOS-PBHICJAKSA-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
(5R)-3-[4-[1-[(2S)-2,3-dihydroxypropanoyl]-3,6-dihydro-2H-pyridin-4-yl]-3,5-difluorophenyl]-5-(1,2-oxazol-3-yloxymethyl)-1,3-oxazolidin-2-one
International Nonproprietary Names Click here for help
INN number INN
8312 posizolid
Synonyms Click here for help
AZD2563 | AZD5847
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Posizolid
Other databases
CAS Registry No. 252260-02-9 (source: Scifinder)
ChEMBL Ligand CHEMBL131854
DrugBank Ligand DB04850
GtoPdb PubChem SID 483123310
PubChem CID 213049
Search Google for chemical match using the InChIKey HBUJYEUPIIJJOS-PBHICJAKSA-N
Search Google for chemicals with the same backbone HBUJYEUPIIJJOS
Search PubMed clinical trials posizolid
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Search PubMed titles/abstracts posizolid
UniChem Compound Search for chemical match using the InChIKey HBUJYEUPIIJJOS-PBHICJAKSA-N
UniChem Connectivity Search for chemical match using the InChIKey HBUJYEUPIIJJOS-PBHICJAKSA-N