riamilovir   Click here for help

GtoPdb Ligand ID: 11996

Synonyms: Triazavirin® | TZV
Compound class: Synthetic organic
Comment: Riamilovir is a synthetic guanine derivative that acts as a broad-spectrum antiviral agent. It disrupts viral transcription and replication, with antiviral activity against a range of RNA viruses. The exact molecular target has not been reported, although molecular docking studies suggest an interaction of riamilovir with SARS-CoV-2 Mpro (3CL protease) [3]. Consequently, riamilovir has been advanced into clinical evaluation for potential anti-SARS-CoV-2 activity.
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 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 144.38
Molecular weight 228.01
XLogP 1.24
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 CSc1[nH]n2c(n1)nnc(c2=O)[N+](=O)[O-]
Isomeric SMILES CSc1nc2nnc(c(=O)n2[nH]1)[N+](=O)[O-]
InChI InChI=1S/C5H4N6O3S/c1-15-5-6-4-8-7-2(11(13)14)3(12)10(4)9-5/h1H3,(H,6,8,9)
InChI Key IDVQGNMSSHPZSJ-UHFFFAOYSA-N
References
1. Hudecová IMJČGKMPL. (2021)
Triazavirin might be the new hope to fight Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2).
Ceska Slov Farm, 70 (1): 18-25. [PMID:34237949]
2. Karpenko I, Deev S, Kiselev O, Charushin V, Rusinov V, Ulomsky E, Deeva E, Yanvarev D, Ivanov A, Smirnova O et al.. (2010)
Antiviral properties, metabolism, and pharmacokinetics of a novel azolo-1,2,4-triazine-derived inhibitor of influenza A and B virus replication.
Antimicrob Agents Chemother, 54 (5): 2017-22. [PMID:20194696]
3. Shahab S, Sheikhi M. (2021)
Triazavirin - Potential Inhibitor for 2019-nCoV Coronavirus M Protease: A DFT Study.
Curr Mol Med, 21 (8): 645-654. [PMID:32436829]