galidesivir   Click here for help

GtoPdb Ligand ID: 11920

Synonyms: BCX-4430 | BCX4430 | Immucillin-A
PDB Ligand
Compound class: Synthetic organic
Comment: Galidesivir (BCX4430) is an adenosine analogue and broad-spectrum antiviral agent [3]. It was originally developed as a treatment for hepatitis C infection, but has subsequently demonstrated activity against Ebola, Marburg and Zika [1] viruses, and was most recently evaluated for potential to treat SARS-CoV-2 infection (COVID-19). Mechanistically it inhibits the virus' RNA-dependent RNA-polymerase (RdRp), that acts as a nonobligate RNA chain terminator.
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 7
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 140.31
Molecular weight 265.12
XLogP -1.06
No. Lipinski's rules broken 1
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 OC[C@H]1N[C@H]([C@@H]([C@@H]1O)O)c1c[nH]c2c1ncnc2N
Isomeric SMILES c1c(c2c([nH]1)c(ncn2)N)[C@H]1[C@@H]([C@@H]([C@H](N1)CO)O)O
InChI InChI=1S/C11H15N5O3/c12-11-8-6(14-3-15-11)4(1-13-8)7-10(19)9(18)5(2-17)16-7/h1,3,5,7,9-10,13,16-19H,2H2,(H2,12,14,15)/t5-,7+,9-,10+/m1/s1
InChI Key AMFDITJFBUXZQN-KUBHLMPHSA-N
References
1. Bernatchez JA, Tran LT, Li J, Luan Y, Siqueira-Neto JL, Li R. (2020)
Drugs for the Treatment of Zika Virus Infection.
J Med Chem, 63 (2): 470-489. [PMID:31549836]
2. Choy KT, Wong AY, Kaewpreedee P, Sia SF, Chen D, Hui KPY, Chu DKW, Chan MCW, Cheung PP, Huang X et al.. (2020)
Remdesivir, lopinavir, emetine, and homoharringtonine inhibit SARS-CoV-2 replication in vitro.
Antiviral Res, 178: 104786. [PMID:32251767]
3. Warren TK, Wells J, Panchal RG, Stuthman KS, Garza NL, Van Tongeren SA, Dong L, Retterer CJ, Eaton BP, Pegoraro G et al.. (2014)
Protection against filovirus diseases by a novel broad-spectrum nucleoside analogue BCX4430.
Nature, 508 (7496): 402-5. [PMID:24590073]