VV116   Click here for help

GtoPdb Ligand ID: 11993

Synonyms: deuremidevir | JT001 | Mindavi® | VV-116 | X6 hydrobromide [PMID: 34584244]
Approved drug
VV116 is an approved drug (China NMPA (2023))
Compound class: Synthetic organic
Comment: VV116 is an orally available, deuterated remdesivir analogue [4-5]. It is a tri-isobutyrate ester prodrug (formulated as the hydrobromide salt) that is converted to an active nucleoside triphosphate (116-NTP) that acts as a viral RNA-dependent RNA polymerase (RdRP) inhibitor. VV116 was developed for antiviral activity against SARS-CoV-2. We drew the chemical structure as represented in Xie et al. (2021) [4].
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)c1cc(c2n1ncnc2N)[2H]
Isomeric SMILES c1([2H])c2n(ncnc2N)c(c1)[C@@]1(O[C@H](COC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H]1OC(=O)C(C)C)C#N
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/i7D
InChI Key RVSSLHFYCSUAHY-QXMJNOOVSA-N
References
1. Cao Z, Gao W, Bao H, Feng H, Mei S, Chen P, Gao Y, Cui Z, Zhang Q, Meng X et al.. (2023)
VV116 versus Nirmatrelvir-Ritonavir for Oral Treatment of Covid-19.
N Engl J Med, 388 (5): 406-417. [PMID:36577095]
2. Fna X, Dai X, Ling Y, Wu L, Tang L, Peng C, Huang C, Liu H, Lu H, Shen X et al.. (2023)
Oral VV116 versus placebo in patients with mild-to-moderate COVID-19 in China: a multicentre, double-blind, phase 3, randomised controlled study.
Lancet Infectious Diseases, Epub ahead of print. DOI: 10.1016/S1473-3099(23)00577-7
3. Qian HJ, Wang Y, Zhang MQ, Xie YC, Wu QQ, Liang LY, Cao Y, Duan HQ, Tian GH, Ma J et al.. (2022)
Safety, tolerability, and pharmacokinetics of VV116, an oral nucleoside analog against SARS-CoV-2, in Chinese healthy subjects.
Acta Pharmacol Sin, 43 (12): 3130-3138. [PMID:35296780]
4. Xie Y, Yin W, Zhang Y, Shang W, Wang Z, Luan X, Tian G, Aisa HA, Xu Y, Xiao G et al.. (2021)
Design and development of an oral remdesivir derivative VV116 against SARS-CoV-2.
Cell Res, 31 (11): 1212-1214. [PMID:34584244]
5. Zhu KW. (2023)
Deuremidevir and Simnotrelvir-Ritonavir for the Treatment of COVID-19.
ACS Pharmacol Transl Sci, 6 (9): 1306-1309. [PMID:37705591]