obeldesivir   Click here for help

GtoPdb Ligand ID: 12901

Synonyms: ATV-006 | ATV006 | compound 5c [PMID: 34450570] | GS-5245 | GS5245
Compound class: Synthetic organic
Comment: Obeldesivir (GS-5245) is an orally bioavailable investigational nucleoside (ATP analogue) antiviral compound [4]. It is an ester prodrug of the predominant remdesivir metabolite GS-441524 [2]. As an inhibitor of viral RNA-dependent RNA polymerase (RdRP) it is likely to have activity against a range of filoviruses, paramyxoviruses, and coronaviruses, including SARS-CoV-2. Postexposure efficacy against SARS-CoV-2 in humans, and Marburg virus and Ebola virus infections (in nonhuman primates) has been reported [1-3,5].

obeldesivir is commercially available from our sponsors

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 10
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 153.76
Molecular weight 361.35
XLogP -1.68
No. Lipinski's rules broken 0

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(=O)OC[C@@H]1[C@H]([C@H]([C@](C#N)(C2=CC=C3C(=NC=NN32)N)O1)O)O
Isomeric SMILES CC(C)C(=O)OC[C@@H]1[C@H]([C@H]([C@](O1)(C#N)C2=CC=C3N2N=CN=C3N)O)O
InChI InChI=1S/C16H19N5O5/c1-8(2)15(24)25-5-10-12(22)13(23)16(6-17,26-10)11-4-3-9-14(18)19-7-20-21(9)11/h3-4,7-8,10,12-13,22-23H,5H2,1-2H3,(H2,18,19,20)/t10-,12-,13-,16+/m1/s1
InChI Key YIHPGVCWGSURHO-VSBTWAGUSA-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/)
Bioactivity Comments
Obeldesivir (5c [4]) inhibits SARS-CoV-2 replication by 99% in vitro (in Vero E6 cells), with an EC50 of 230 nM, and has high oral bioavailability in mice [4].
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CoV RNA-dependent RNA polymerase SARS-CoV-2 Inhibitor Inhibition - - - 4
⤷ [4]