(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编号: 72978
• 分子式: C42H70O11
• 平均质量: 750.9986
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: salinomycin
• 别名: 盐霉素; 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.)

登记号

• CAS号: 53003-10-4; 55721-31-8
• EC号: 258-290-1
• PubChem SID: 162037898
• PubChem CID: 3085092; 72370
• ATC码: QP51AH01
• CHEMBL: 1208572
• 维基百科标题: Salinomycin

理论计算性质

• Acid pKa: 4.4524813
• 质子受体: 11
• 质子供体: 4
• LogD (pH = 5.5): 6.428476
• LogD (pH = 7.4): 4.664844
• Log P: 7.5118465
• 摩尔折射率: 200.0663 cm^3
• 极化性: 80.1629 Å^3
• 极化表面积: 161.21 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: alcohols: soluble; carbon tetrachloride: soluble; chloroform: soluble; DMSO: soluble; ethers and esters: soluble; H2O: insoluble; hexane: soluble
• 外观: Brown Solid
• 熔点: 112.5-113.5 °C(lit.)
• 闪点: 188.6 °F; 87 °C

安全信息

• 保存条件: -20°C; Hygroscopic, Refrigerator, Under Inert Atmosphere
• RTECS编号: VO8620000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 3462
• 德国WGK号: 2; 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• 生物来源: from Streptomyces albus
• 运输包装: dry ice
• Empirical Formula (Hill Notation): C42H70O11

详细说明

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.

参考文献

• 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)