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
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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
1. Chakraborty S, Mallick D, Goswami M, Guengerich FP, Chakrabarty A, Chowdhury G. (2022)
The Natural Products Withaferin A and Withanone from the Medicinal Herb Withania somnifera Are Covalent Inhibitors of the SARS-CoV-2 Main Protease.
J Nat Prod, 85 (10): 2340-2350. [PMID:36098617]
2. Freitas Misakyan MF, Wijeratne EMK, Issa ME, Xu YM, Monteillier A, Gunatilaka AAL, Cuendet M. (2021)
Structure-Activity Relationships of Withanolides as Antiproliferative Agents for Multiple Myeloma: Comparison of Activity in 2D Models and a 3D Coculture Model.
J Nat Prod, 84 (8): 2321-2335. [PMID:34445874]
3. Glotter E. (1991)
Withanolides and related ergostane-type steroids.
Nat Prod Rep, 8 (4): 415-40. [PMID:1787922]
4. Perestelo NR, Llanos GG, Reyes CP, Amesty A, Sooda K, Afshinjavid S, Jiménez IA, Javid F, Bazzocchi IL. (2019)
Expanding the Chemical Space of Withaferin A by Incorporating Silicon To Improve Its Clinical Potential on Human Ovarian Carcinoma Cells.
J Med Chem, 62 (9): 4571-4585. [PMID:31008605]