umifenovir   Click here for help

GtoPdb Ligand ID: 11089

Synonyms: AR-1I9514 | Arbidol®
PDB Ligand
Compound class: Synthetic organic
Comment: Umifenovir is an indole-based antiviral drug. It is a viral entry inhibitor [3] and also acts to modulate the host immune response (induces interferon-production, stimulates macrophages phagocytosis).
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 8
Topological polar surface area 80
Molecular weight 476.08
XLogP 5.1
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 CCOC(=O)c1c(CSc2ccccc2)n(c2c1c(CN(C)C)c(O)c(c2)Br)C
Isomeric SMILES CCOC(=O)c1c(CSc2ccccc2)n(c2c1c(CN(C)C)c(O)c(c2)Br)C
InChI InChI=1S/C22H25BrN2O3S/c1-5-28-22(27)20-18(13-29-14-9-7-6-8-10-14)25(4)17-11-16(23)21(26)15(19(17)20)12-24(2)3/h6-11,26H,5,12-13H2,1-4H3
InChI Key KCFYEAOKVJSACF-UHFFFAOYSA-N
References
1. Hulseberg CE, Fénéant L, Szymańska-de Wijs KM, Kessler NP, Nelson EA, Shoemaker CJ, Schmaljohn CS, Polyak SJ, White JM. (2019)
Arbidol and Other Low-Molecular-Weight Drugs That Inhibit Lassa and Ebola Viruses.
J Virol, 93 (8). [PMID:30700611]
2. Ianevski A, Yao R, Fenstad MH, Biza S, Zusinaite E, Reisberg T, Lysvand H, Løseth K, Landsem VM, Malmring JF et al.. (2020)
Potential Antiviral Options against SARS-CoV-2 Infection.
Viruses, 12 (6). [PMID:32545799]
3. Leneva IA, Russell RJ, Boriskin YS, Hay AJ. (2009)
Characteristics of arbidol-resistant mutants of influenza virus: implications for the mechanism of anti-influenza action of arbidol.
Antiviral Res, 81 (2): 132-40. [PMID:19028526]
4. Pécheur EI, Borisevich V, Halfmann P, Morrey JD, Smee DF, Prichard M, Mire CE, Kawaoka Y, Geisbert TW, Polyak SJ. (2016)
The Synthetic Antiviral Drug Arbidol Inhibits Globally Prevalent Pathogenic Viruses.
J Virol, 90 (6): 3086-92. [PMID:26739045]