withaferin A   Click here for help

GtoPdb Ligand ID: 13097

Compound class: Natural product
Comment: Withaferin A was the first withanolide class phytochemical to be isolated (from Withania somnifera, a.k.a. winter cherry or ashwagandha) [3]. More than 300 withanolides have subsequently been isolated from other plant species, and many pharmacological actions have been associated with them.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 96.36
Molecular weight 470.6
XLogP 3.99
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC1=C(CO)C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@@H]5[C@@]6([C@H](C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)O)O5
Isomeric SMILES CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)CO
InChI InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
InChI Key DBRXOUCRJQVYJQ-CKNDUULBSA-N
Bioactivity Comments
Potent (nanomolar) antiproliferative effects against human cancer cell lines have been reported [4], as has inhibition of NF-κB transcriptional activity (IC50 47 nM) [2]. The SARS-CoV-2 main protease (Mpro) is inhibited by withaferin A [1].
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CoV 3C-like (main) protease SARS-CoV-2 Inhibitor Inhibition 6.3 pIC50 - 1
pIC50 6.3 (IC50 5.4x10-7 M) [1]