EIDD-2801   

GtoPdb Ligand ID: 10737

Compound class: Synthetic organic
Comment: EIDD-2801 is the isopropylester prodrug of the ribonucleoside analogue β-D-N4-hydroxycytidine (EIDD-1931, or N-hydroxycytidine) [1]. It was originally designed by Emory University chemists 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 [2]. The active form of EIDD-2801 exists in two tautomeric forms, one which is a uridine mimic (pairs with adenosine), and the second which mimics cytidine (pairs with guanosine). During RNA replication switching between these tautomers causes mismatches and leads to catastrophic mutation within the new viral RNA transcripts which render it non-functional. Remdesivir is another nucleoside analogue that is being evaluated in human trials for efficacy against SARS-CoV-2 infection. The active forms of both compounds block viral RNA-dependent RNA polymerase to prevent virus replication, but in slightly different ways, suggesting that their effects may be complementary. Another difference between remdesivir and EIDD-2801 is that while remdesivir needs to be administered intravenously within a medical setting, EIDD-2801 is orally bioavailable, so could be taken at home. This offers the potential for treatment to be initiated earlier in the course of the disease, before more severe symptoms develop.
2D Structure

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

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

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
Compound class Synthetic organic
Database Links
CAS Registry No. 2349386-89-4 (source: PubChem)
DrugCentral Ligand 5377
GtoPdb PubChem SID 405067330
PubChem CID 145996610
Search Google for chemical match using the InChIKey HTNPEHXGEKVIHG-QCNRFFRDSA-N
Search Google for chemicals with the same backbone HTNPEHXGEKVIHG
Search UniChem for chemical match using the InChIKey HTNPEHXGEKVIHG-QCNRFFRDSA-N
Search UniChem for chemicals with the same backbone HTNPEHXGEKVIHG