zosurabalpin   Click here for help

GtoPdb Ligand ID: 12950

Synonyms: Abx MCP | RG6006 | RO7223280
PDB Ligand
Compound class: Synthetic organic
Comment: Zosurabalpin is a macrolide antibacterial that is being developed by Hoffmann-La Roche [3]. It is one of the compounds that are claimed in Hoffmann-La Roche's patent WO2019206853A1 [1].
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 13
Hydrogen bond donors 7
Rotatable bonds 11
Topological polar surface area 229.57
Molecular weight 790.98
XLogP 1.57
No. Lipinski's rules broken 4
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 CN1[C@@H](CC2=CNC3=C2C=CC=C3)C(=O)NCC4=C(C=CC=C4SC5=NC=CC=C5CN[C@@H](CCCN)C(=O)N[C@@H](CCCCN)C1=O)C6=CC=C(C=C6)C(=O)O
Isomeric SMILES CN1[C@H](C(=O)NCC2=C(C=CC=C2SC3=C(CN[C@H](C(=O)N[C@H](C1=O)CCCCN)CCCN)C=CC=N3)C4=CC=C(C=C4)C(=O)O)CC5=CNC6=CC=CC=C65
InChI InChI=1S/C43H50N8O5S/c1-51-37(23-30-25-47-34-12-3-2-10-32(30)34)40(53)49-26-33-31(27-16-18-28(19-17-27)43(55)56)11-6-15-38(33)57-41-29(9-8-22-46-41)24-48-35(14-7-21-45)39(52)50-36(42(51)54)13-4-5-20-44/h2-3,6,8-12,15-19,22,25,35-37,47-48H,4-5,7,13-14,20-21,23-24,26,44-45H2,1H3,(H,49,53)(H,50,52)(H,55,56)/t35-,36-,37-/m0/s1
InChI Key NJFUXFYUHIHHOJ-FSEITFBQSA-N
References
1. Bleicher K, Cheang D, Di Giorgio P, Hu T, Jenny C, Mattei P, Schmitz P, Stoll T. (2019)
Peptide macrocycles against acinetobacter baumannii.
Patent number: WO2019206853A1. Assignee: F. Hoffmann-La Roche Ag. Priority date: 23/04/2019. Publication date: 31/10/2019.
2. 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]
3. Zampaloni C, Mattei P, Bleicher K, Winther L, Thäte C, Bucher C, Adam JM, Alanine A, Amrein KE, Baidin V et al.. (2024)
A novel antibiotic class targeting the lipopolysaccharide transporter.
Nature, 625 (7995): 566-571. [PMID:38172634]