nafithromycin   Click here for help

GtoPdb Ligand ID: 10834

Synonyms: WCK 4873 | WCK-4873 | WCK4873
Compound class: Synthetic organic
Comment: Nafithromycin (WCK-4873) is a ketolide antibacterial with Gram-positive activity [2-3].
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 15
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 252.42
Molecular weight 858.42
XLogP 3.44
No. Lipinski's rules broken 1

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[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)[C@H]2/C(=N/O[C@H](c1nnc(s1)c1ccccn1)C)/N)C)C)(C)OC
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)[C@H]2/C(=N/O[C@H](c1nnc(s1)c1ccccn1)C)/N)C)C)(C)OC
InChI InChI=1S/C42H62N6O11S/c1-13-28-42(9)30(29(39(53)58-42)35(43)47-59-25(7)36-45-46-37(60-36)26-16-14-15-17-44-26)22(4)31(49)20(2)19-41(8,54-12)34(23(5)32(50)24(6)38(52)56-28)57-40-33(51)27(48(10)11)18-21(3)55-40/h14-17,20-25,27-30,33-34,40,51H,13,18-19H2,1-12H3,(H2,43,47)/t20-,21-,22-,23+,24-,25+,27+,28-,29-,30+,33-,34-,40+,41-,42-/m1/s1
InChI Key RLFCSBSRGRJFRO-QAOQTAGDSA-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. Butler MS, Henderson IR, Capon RJ, Blaskovich MAT. (2023)
Antibiotics in the clinical pipeline as of December 2022.
J Antibiot (Tokyo), 76 (8): 431-473. [PMID:37291465]
2. Flamm RK, Rhomberg PR, Sader HS. (2017)
In Vitro Activity of the Novel Lactone Ketolide Nafithromycin (WCK 4873) against Contemporary Clinical Bacteria from a Global Surveillance Program.
Antimicrob Agents Chemother, 61 (12). [PMID:28971877]
3. Hackel MA, Karlowsky JA, Dressel D, Sahm DF. (2017)
Determination of Disk Diffusion and MIC Quality Control Ranges for Nafithromycin (WCK 4873), a New Lactone-Ketolide.
J Clin Microbiol, 55 (10): 3021-3027. [PMID:28747372]
4. Iwanowski P, Bhatia A, Gupta M, Patel A, Chavan R, Yeole R, Friedland D. (2019)
Safety, tolerability and pharmacokinetics of oral nafithromycin (WCK4873) after single or multiple doses and effects of food on single-dose bioavailability in healthy adult subjects.
Antimicrob Agents Chemother, 63 (12). [PMID:31591119]