decanoyl-RVKR-chloromethylketone   Click here for help

GtoPdb Ligand ID: 11258

Synonyms: decanoyl-Arg-Val-Lys-Arg-CMK | Decanoyl-RVKR-CMK
Compound class: Synthetic organic
Comment: Decanoyl-RVKR-CMK is a cell‐permeable and irreversible inhibitor of proprotein convertase (PC) enzymes [2]. The PC family of serine proteases includes furin. Furin-mediated cleavage of HIV-1 envelope glycoprotein 160 (gp160) is essential for fusion of the viral envelope with the host cell membrane [2].

SARS-CoV-2: Decanoyl-RVKR-CMK inhibits cleavage of SARS-CoV-2 spike protein by furin, at the furin cleavage site, and this translates to an antiviral effect in vitro [1].
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 16
Hydrogen bond donors 11
Rotatable bonds 36
Topological polar surface area 283.29
Molecular weight 743.49
XLogP 3.78
No. Lipinski's rules broken 3
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 NCCCC[C@@H](C(=O)N[C@H](C(=O)CCl)CCCNC(=N)N)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CCCCCCCCC)CCCNC(=N)N
Isomeric SMILES NCCCC[C@@H](C(=O)N[C@H](C(=O)CCl)CCCNC(=N)N)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CCCCCCCCC)CCCNC(=N)N
InChI InChI=1S/C34H66ClN11O5/c1-4-5-6-7-8-9-10-18-28(48)43-25(17-14-21-42-34(39)40)31(50)46-29(23(2)3)32(51)45-26(15-11-12-19-36)30(49)44-24(27(47)22-35)16-13-20-41-33(37)38/h23-26,29H,4-22,36H2,1-3H3,(H,43,48)(H,44,49)(H,45,51)(H,46,50)(H4,37,38,41)(H4,39,40,42)/t24-,25-,26-,29-/m0/s1
InChI Key NHBJTTGFHCHQHS-VZTVMPNDSA-N
Bioactivity Comments
In a VeroE6 cell plaque reduction assay in which the cells were expressing the wild-type spike protein, decanoyl-RVKR-CMK inhibited SARS-CoV-2 plaque formation with an IC50 of 57 nM [1]. In the same assay the TMPRSS2 inhibitor camostat gave an IC50 of 25 nM.