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lanopepden   Click here for help

GtoPdb Ligand ID: 14318

Synonyms: GSK1322322
Compound class: Synthetic organic
Comment: Lanopepden is a first-in-class antibacterial that targets peptide deformylase (PDF), a bacterial enzyme essential for protein maturation [3-4].
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 9
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 122.1
Molecular weight 479.55
XLogP 1.1
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 CC1=NC(=C(C(=N1)NNC(=O)[C@H](CC2CCCC2)CN(C=O)O)F)N3CCN4CCOC[C@@H]4C3
Isomeric SMILES CC1=NC(=C(C(=N1)N2CCN3CCOC[C@@H]3C2)F)NNC(=O)[C@H](CC4CCCC4)CN(C=O)O
InChI InChI=1S/C22H34FN7O4/c1-15-24-20(19(23)21(25-15)29-7-6-28-8-9-34-13-18(28)12-29)26-27-22(32)17(11-30(33)14-31)10-16-4-2-3-5-16/h14,16-18,33H,2-13H2,1H3,(H,27,32)(H,24,25,26)/t17-,18+/m1/s1
InChI Key SWHNZGMQMGFQGW-MSOLQXFVSA-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/)
References
1. Corey R, Naderer OJ, O'Riordan WD, Dumont E, Jones LS, Kurtinecz M, Zhu JZ. (2014)
Safety, tolerability, and efficacy of GSK1322322 in the treatment of acute bacterial skin and skin structure infections.
Antimicrob Agents Chemother, 58 (11): 6518-27. [PMID:25136015]
2. Hoover JL, Singley CM, Elefante P, DeMarsh P, Zalacain M, Rittenhouse S. (2017)
Reducing Antibacterial Development Risk for GSK1322322 by Exploring Potential Human Dose Regimens in Nonclinical Efficacy Studies Using Immunocompetent Rats.
Antimicrob Agents Chemother, 61 (11). [PMID:28807913]
3. Min S, Ingraham K, Huang J, McCloskey L, Rilling S, Windau A, Pizzollo J, Butler D, Aubart K, Miller LA et al.. (2015)
Frequency of Spontaneous Resistance to Peptide Deformylase Inhibitor GSK1322322 in Haemophilus influenzae, Staphylococcus aureus, Streptococcus pyogenes, and Streptococcus pneumoniae.
Antimicrob Agents Chemother, 59 (8): 4644-52. [PMID:26014938]
4. O'Dwyer K, Hackel M, Hightower S, Hoban D, Bouchillon S, Qin D, Aubart K, Zalacain M, Butler D. (2013)
Comparative analysis of the antibacterial activity of a novel peptide deformylase inhibitor, GSK1322322.
Antimicrob Agents Chemother, 57 (5): 2333-42. [PMID:23478958]