azvudine   Click here for help

GtoPdb Ligand ID: 13479

Synonyms: RO-0622
Compound class: Synthetic organic
Comment: Azvudine is a nucleoside analogue that was first identified as an inhibitor of the HIV-1 RNA-dependent RNA polymerase (RdRp) [4]. It has more recently been reported to inhibit RdRp from the SARS-CoV-2 betacoronavirus [5]. The active triphosphate metabolite concentrates in the thymus and peripheral blood mononuclear cells, and oral treatment induces curative mechanisms in preclinical models.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 120.74
Molecular weight 286.22
XLogP -1.43
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES C1=CN([C@H]2[C@H]([C@@H]([C@](CO)(N=[N+]=[N-])O2)O)F)C(=O)N=C1N
Isomeric SMILES C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@](O2)(CO)N=[N+]=[N-])O)F
InChI InChI=1S/C9H11FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,17-18H,3H2,(H2,11,13,19)/t5-,6-,7+,9+/m0/s1
InChI Key KTOLOIKYVCHRJW-XZMZPDFPSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-amino-1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Synonyms Click here for help
RO-0622
Database Links Click here for help
CAS Registry No. 1011529-10-4 (source: PubChem)
ChEMBL Ligand CHEMBL519846
GtoPdb PubChem SID 500839889
PubChem CID 24769759
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