salinomycin   Click here for help

GtoPdb Ligand ID: 11088

Synonyms: Coxistac® | Procoxacin®
Compound class: Synthetic organic
Comment: Salinomycin is an ionophore antibacterial, 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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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
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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 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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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 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]