salinomycin   Click here for help

GtoPdb Ligand ID: 11088

Synonyms: Coxistac® | Procoxacin®
Compound class: Synthetic organic
Comment: Salinomycin is an ionophore antibiotic, from which narasin was derived. It is primarily used in veterinary practice. Salinomycin has potent antimicrobial activity against Gram-positive bacteria and is inactive against Gram-negative bacteria [2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 161.21
Molecular weight 750.49
XLogP 5.11
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC[C@H]([C@H]1O[C@]2(C=C[C@H]([C@@]3(O2)CC[C@@](O3)(C)[C@H]2CC[C@]([C@@H](O2)C)(O)CC)O)[C@@H](C[C@@H]1C)C)C(=O)[C@H]([C@H]([C@@H]([C@@H]1O[C@H](CC[C@@H]1C)[C@H](C(=O)O)CC)C)O)C
Isomeric SMILES CC[C@H]([C@H]1O[C@]2(C=C[C@H]([C@@]3(O2)CC[C@@](O3)(C)[C@H]2CC[C@]([C@@H](O2)C)(O)CC)O)[C@@H](C[C@@H]1C)C)C(=O)[C@H]([C@H]([C@@H]([C@@H]1O[C@H](CC[C@@H]1C)[C@H](C(=O)O)CC)C)O)C
InChI InChI=1S/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1
InChI Key KQXDHUJYNAXLNZ-XQSDOZFQSA-N
References
1. Antoszczak M, Huczyński A. (2015)
Anticancer Activity of Polyether Ionophore-Salinomycin.
Anticancer Agents Med Chem, 15 (5): 575-91. [PMID:25553435]
2. Antoszczak M, Maj E, Napiórkowska A, Stefańska J, Augustynowicz-Kopeć E, Wietrzyk J, Janczak J, Brzezinski B, Huczyński A. (2014)
Synthesis, anticancer and antibacterial activity of salinomycin N-benzyl amides.
Molecules, 19 (12): 19435-59. [PMID:25429565]
3. Gupta PB, Onder TT, Jiang G, Tao K, Kuperwasser C, Weinberg RA, Lander ES. (2009)
Identification of selective inhibitors of cancer stem cells by high-throughput screening.
Cell, 138 (4): 645-659. [PMID:19682730]
4. Huczynski A. (2012)
Salinomycin: a new cancer drug candidate.
Chem Biol Drug Des, 79 (3): 235-8. [PMID:22145602]
5. Ianevski A, Yao R, Fenstad MH, Biza S, Zusinaite E, Reisberg T, Lysvand H, Løseth K, Landsem VM, Malmring JF et al.. (2020)
Potential Antiviral Options against SARS-CoV-2 Infection.
Viruses, 12 (6). [PMID:32545799]