(2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(2S,5S,7R,9S,10S,12R,15R)-2-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid

• ChemBase ID: 72978
• Molecular Formular: C42H70O11
• Molecular Mass: 750.9986
• Monoisotopic Mass: 750.49181306
• SMILES: C1[C@H]([C@@]2(O[C@@H]([C@H]1C)[C@H](C(=O)[C@H]([C@@H](O)[C@@H]([C@@H]1O[C@H](CC[C@@H]1C)[C@H](C(=O)O)CC)C)C)CC)O[C@]1([C@@H](C=C2)O)CC[C@](O1)([C@@H]1O[C@H]([C@](CC1)(CC)O)C)C)C
• 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
• 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
• InChIKey: KQXDHUJYNAXLNZ-XQSDOZFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(2S,5S,7R,9S,10S,12R,15R)-2-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5^7.3^5]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid; (2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(2S,5S,7R,9S,10S,12R,15R)-2-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5^{7}.3^{5}]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid
• IUPAC Traditional name: salinomycin
• Synonyms: Antibiotic 61477, Coxxistac; Salinomycin, Ready Made Solution; Procoxacin; Salinomycin; Salinomycin; (2R)-2-((5S)-6-{5-[(10S,12R)-2-((6S,5R)-5-Ethyl-5-hydroxy-6-methylperhydro-2H-pyran-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-9-yl](1S,2S,3S,5R)-2-hydroxy-1,3-dimethyl-4-oxoheptyl}-5-methylperhydro-2H-pyran-2-yl)butanoic Acid Sodium; Bio-Cox; Sacox; Salocin; Salinomycin Sodium Salt (12% min.); 盐霉素

Database IDs

• CAS Number: 53003-10-4; 55721-31-8
• EC Number: 258-290-1
• PubChem SID: 162037898
• PubChem CID: 72370; 3085092
• ATC CODE: QP51AH01
• CHEMBL: 1208572
• Wikipedia Title: Salinomycin

CALCULATED PROPERTIES

• Acid pKa: 4.4524813
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 6.428476
• LogD (pH = 7.4): 4.664844
• Log P: 7.5118465
• Molar Refractivity: 200.0663 cm^3
• Polarizability: 80.1629 Å^3
• Polar Surface Area: 161.21 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: alcohols: soluble; carbon tetrachloride: soluble; chloroform: soluble; DMSO: soluble; ethers and esters: soluble; H2O: insoluble; hexane: soluble
• Apperance: Brown Solid
• Melting Point: 112.5-113.5 °C(lit.)
• Flash Point: 188.6 °F; 87 °C

Safety Information

• Storage Condition: -20°C; Hygroscopic, Refrigerator, Under Inert Atmosphere
• RTECS: VO8620000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 2; 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Biological Source: from Streptomyces albus
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C42H70O11

DETAILS

Selleck Chemicals - S2352

Related research area: Infection

Sigma Aldrich - S6201

Physical form
The product is supplied as a 2 mg/mL (2.66 mM) solution in DMSO, 0.2 μm-filtered.
Biochem/physiol Actions
Salinomycin is a monocarboxylic polyether antibiotic with unique tricyclic spiroketal ring systems and an unsaturated six-membered ring in the molecule.1 Salinomycin has antimicrobial and anticoccidial activities. It is an alkali ion carrier with affinity for cations and preference for K+ over other monovalent and divalent cations.1 Polyether antibiotics (also called carboxylic ionophores) facilitate bidirectional ion flux through the lipid barrier of membranes causing interference with natural ion transport systems both in prokaryotic and eukaryotic cells. Tumor cells express elevated levels of various types of K+ channels, which enhances cell proliferation.2,3 Thus, drugs acting as channel blockers inhibit cell proliferation. Being a highly selective potassium ionophore, salinomycin may interfere with potassium channels function in cancer stem cells (CSCs). Established cancer therapies may fail because they kill the bulk tumor cells, but do not eliminate CSCs. Studies indicate that Salinomycin selectively eradicates breast CSCs.3 Salinomycin may eliminate CSCs by inducing their differentiation. salinomycin suppresses the metastatic migration of 4T1 cells to the lungs.3

Sigma Aldrich - S4526

Biochem/physiol Actions
Polyether potassium ionophore

Toronto Research Chemicals - S088800

Salinomycin is an ionophore antibiotic used in farming for the prevention of coccidiodomycosis in poultry and to alter gut flora in order to improve nutrient absorption in ruminants. An anticoccidial agent.

REFERENCES

• http://en.wikipedia.org/wiki/Salinomycin
• Porter, C., et al.: Poult Sci., 34, 995 (1955)
• Hancock, R., et al.: Lancet, 349, 418 (1955)
• Ogita, A., et al.: Toxicology, 215, 205 (1955)
• Usuki, Y., et al.: Bioorg. Med. Chem. Lett., 16, 1553 (1955)
• Ogita, A., et al.: J. Antibiot., 60, 511 (1955)