GS-621763   Click here for help

GtoPdb Ligand ID: 11840

Synonyms: GS621763
Compound class: Synthetic organic
Comment: GS-621763 is an orally bioavailable triester prodrug of remdesivir (GS-5734) [1]. It is metabolised into the same active nucleoside triphosphate as remdesivir. Like its parent, this prodrug results in inhibition of viral RNA-dependent RNA polymerase (RdRP), and it has been evaluated against SARS-CoV-2 RdRP. GS-621763 has antiviral activity in vitro (in human primary cell systems) and has demonstrated in vivo therapeutic efficacy in mice infected with SARS-CoV-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 11
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 168.13
Molecular weight 501.22
XLogP 1.38
No. Lipinski's rules broken 2
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 N#C[C@]1(O[C@@H]([C@H]([C@H]1OC(=O)C(C)C)OC(=O)C(C)C)COC(=O)C(C)C)c1ccc2n1ncnc2N
Isomeric SMILES CC(C)C(=O)OC[C@H]1O[C@](C#N)([C@H](OC(=O)C(C)C)[C@@H]1OC(=O)C(C)C)c1ccc2n1ncnc2N
InChI InChI=1S/C24H31N5O7/c1-12(2)21(30)33-9-16-18(34-22(31)13(3)4)19(35-23(32)14(5)6)24(10-25,36-16)17-8-7-15-20(26)27-11-28-29(15)17/h7-8,11-14,16,18-19H,9H2,1-6H3,(H2,26,27,28)/t16-,18-,19-,24+/m1/s1
InChI Key RVSSLHFYCSUAHY-JQGROFRJSA-N
References
1. Schäfer A, Martinez DR, Won JJ, Moreira FR, Brown AJ, Gully KL, Kalla R, Chun K, Du Pont V, Babusis D et al.. (2021)
Therapeutic efficacy of an oral nucleoside analog of remdesivir against SARS-CoV-2 pathogenesis in mice.
bioRxiv, Preprint. DOI: 10.1101/2021.09.13.460111 [PMID:34545367]