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 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 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
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 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
References
1. Alsultan A, Furin JJ, Du Bois J, van Brakel E, Chheng P, Venter A, Thiel B, Debanne SA, Boom WH, Diacon AH et al.. (2017)
Population Pharmacokinetics of AZD-5847 in Adults with Pulmonary Tuberculosis.
Antimicrob Agents Chemother, 61 (10). [PMID:28739794]
2. Balasubramanian V, Solapure S, Iyer H, Ghosh A, Sharma S, Kaur P, Deepthi R, Subbulakshmi V, Ramya V, Ramachandran V et al.. (2014)
Bactericidal activity and mechanism of action of AZD5847, a novel oxazolidinone for treatment of tuberculosis.
Antimicrob Agents Chemother, 58 (1): 495-502. [PMID:24189255]
3. Furin JJ, Du Bois J, van Brakel E, Chheng P, Venter A, Peloquin CA, Alsultan A, Thiel BA, Debanne SM, Boom WH et al.. (2016)
Early Bactericidal Activity of AZD5847 in Patients with Pulmonary Tuberculosis.
Antimicrob Agents Chemother, 60 (11): 6591-6599. [PMID:27550361]
4. Leach KL, Swaney SM, Colca JR, McDonald WG, Blinn JR, Thomasco LM, Gadwood RC, Shinabarger D, Xiong L, Mankin AS. (2007)
The site of action of oxazolidinone antibiotics in living bacteria and in human mitochondria.
Mol Cell, 26 (3): 393-402. [PMID:17499045]
5. Wookey A, Turner PJ, Greenhalgh JM, Eastwood M, Clarke J, Sefton C. (2004)
AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro.
Clin Microbiol Infect, 10 (3): 247-54. [PMID:15008947]