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olgotrelvir   Click here for help

GtoPdb Ligand ID: 13926

Synonyms: STI-1558 | STI1558
Compound class: Synthetic organic
Comment: Olgotrelvir (STI-1558) is a novel antiviral prodrug compound that is active as a dual inhibitor of viral and host proteases [2]. The active form is called AC1115. Mechanistically olgotrelvir inhibits SARS-CoV-2 3CL protease (Mpro) and human cathepsin L. It disrupts both viral entry (host protease dependent) and replication (Mpro dependent) and was developed as a potential treatment for COVID-19.
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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Click here for structure editor
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 11
Hydrogen bond donors 6
Rotatable bonds 12
Topological polar surface area 182.31
Molecular weight 494.56
XLogP -0.42
No. Lipinski's rules broken 2

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)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(O)S(=O)(=O)O)NC(=O)C2=CC3=C(C=CC=C3)N2
Isomeric SMILES CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(O)S(=O)(=O)O)NC(=O)C2=CC3=CC=CC=C3N2
InChI InChI=1S/C22H30N4O7S/c1-12(2)9-16(25-21(29)17-10-13-5-3-4-6-15(13)24-17)20(28)26-18(22(30)34(31,32)33)11-14-7-8-23-19(14)27/h3-6,10,12,14,16,18,22,24,30H,7-9,11H2,1-2H3,(H,23,27)(H,25,29)(H,26,28)(H,31,32,33)/t14-,16-,18-,22?/m0/s1
InChI Key IICZZAVAIPTWCL-HBIMBUPRSA-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. Jiang R, Han B, Xu W, Zhang X, Peng C, Dang Q, Sun W, Lin L, Lin Y, Fan L et al.. (2024)
Olgotrelvir as a Single-Agent Treatment of Nonhospitalized Patients with Covid-19.
NEJM Evid, 3 (6): EVIDoa2400026. [PMID:38804790]
2. Mao L, Shaabani N, Zhang X, Jin C, Xu W, Argent C, Kushnareva Y, Powers C, Stegman K, Liu J et al.. (2024)
Olgotrelvir, a dual inhibitor of SARS-CoV-2 Mpro and cathepsin L, as a standalone antiviral oral intervention candidate for COVID-19.
Med, 5 (1): 42-61.e23. [PMID:38181791]