molnupiravir   Click here for help

GtoPdb Ligand ID: 10737

Synonyms: EIDD-2801 | EIDD2801 | MK-4482 | MK4482
Compound class: Synthetic organic
Comment: Molnupiravir (EIDD-2801, MK-4482) is a clinical stage, oral, broad-spectrum antiviral drug [1,3]. The proposed INN molnupiravir was released by the WHO in a special release to cover COVID-related therapeutics in October 2020 (Proposed INN: List 124- COVID-19). Chemically molnupiravir is the isopropylester prodrug of the ribonucleoside analogue β-D-N4-hydroxycytidine (EIDD-1931, or N-hydroxycytidine) [4-5]. EIDD-2801 was originally designed by Emory University scientists to inhibit replication of influenza virus. It has subsequently been tested for activity against other RNA viruses, including pandemic SARS-CoV-2, SARS-CoV and MERS-CoV [7]. EIDD-2801 is being progressed for COVID-19 in a collaboration between Ridgeback Biotherapeutics and Merck. In vivo therapeutic and prophylactic potential was reported in a peer reviewed manuscript in February 2021 [6].
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 6
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 143.14
Molecular weight 329.12
XLogP 0
No. Lipinski's rules broken 0
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 ONc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COC(=O)C(C)C
Isomeric SMILES ONc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COC(=O)C(C)C
InChI InChI=1S/C13H19N3O7/c1-6(2)12(19)22-5-7-9(17)10(18)11(23-7)16-4-3-8(15-21)14-13(16)20/h3-4,6-7,9-11,17-18,21H,5H2,1-2H3,(H,14,15,20)/t7-,9-,10-,11-/m1/s1
InChI Key HTNPEHXGEKVIHG-QCNRFFRDSA-N
Classification Click here for help
Compound class Synthetic organic
Synonyms Click here for help
EIDD-2801 | EIDD2801 | MK-4482 | MK4482
Database Links Click here for help
CAS Registry No. 2349386-89-4 (source: WHO INN record)
DrugCentral Ligand 5377
GtoPdb PubChem SID 405067330
PubChem CID 145996610
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Search UniChem for chemical match using the InChIKey HTNPEHXGEKVIHG-QCNRFFRDSA-N
Search UniChem for chemicals with the same backbone HTNPEHXGEKVIHG