ONO-5334   Click here for help

GtoPdb Ligand ID: 10747

Synonyms: ONO 5334 | ONO5334
Compound class: Synthetic organic
Comment: ONO-5334 is a cysteine protease inhibitor with activity against cathepsin K. It was an oral drug lead that was considered as a bone resorption inhibitor for the treatment of postmenopausal osteoporosis. ONO-5334 has some antiviral activity against SARS-CoV-2, and antagonises viral replication in human iPSC-derived pneumocyte-like cells [2].
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 125.4
Molecular weight 438.23
XLogP 3.87
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 O=C(C1CCCCCC1)N[C@H](C(=O)C(=O)N/N=C/1\SC[C@H](N1C)C)C1CCOCC1
Isomeric SMILES O=C(C1CCCCCC1)N[C@H](C(=O)C(=O)N/N=C/1\SC[C@H](N1C)C)C1CCOCC1
InChI InChI=1S/C21H34N4O4S/c1-14-13-30-21(25(14)2)24-23-20(28)18(26)17(15-9-11-29-12-10-15)22-19(27)16-7-5-3-4-6-8-16/h14-17H,3-13H2,1-2H3,(H,22,27)(H,23,28)/b24-21-/t14-,17+/m1/s1
InChI Key BTZCSXIUAFVRTE-CHGLIHOBSA-N
References
1. Eastell R, Nagase S, Small M, Boonen S, Spector T, Ohyama M, Kuwayama T, Deacon S. (2014)
Effect of ONO-5334 on bone mineral density and biochemical markers of bone turnover in postmenopausal osteoporosis: 2-year results from the OCEAN study.
J Bone Miner Res, 29 (2): 458-66. [PMID:23873670]
2. Riva L, Yuan S, Yin X, Martin-Sancho L, Matsunaga N, Pache L, Burgstaller-Muehlbacher S, De Jesus PD, Teriete P, Hull MV et al.. (2020)
Discovery of SARS-CoV-2 antiviral drugs through large-scale compound repurposing.
Nature, [Epub ahead of print]. DOI: 10.1038/s41586-020-2577-1