(1S,3R,4R,7R,9R,11R,15S,16S,17R,18S,19Z,21Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid

• ChemBase编号: 131813
• 分子式: C47H75NO17
• 平均质量: 926.0949
• 单一同位素质量: 925.50349995
• SMILES: C[C@H]1/C=C\C=C/CC/C=C\C=C/C=C\C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H]([C@@H](CC[C@H](C[C@H](C[C@H](CC(=O)O[C@H]([C@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)O
• Canonical SMILES: O[C@@H]1CC[C@@H](O)[C@H](O)C[C@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](/C=C\C=C/C=C\C=C/CC/C=C\C=C/[C@@H]([C@H]([C@@H]([C@@H](OC(=O)C[C@@H](C[C@@H](C1)O)O)C)C)O)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=O)O
• InChI: InChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5-,10-8-,13-11-,14-12-,17-15-,18-16-/t27-,28+,29-,30+,31+,32+,33+,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
• InChIKey: VQOXZBDYSJBXMA-HBQQHZFTSA-N

名称和登记号

名称

• IUPAC标准名: (1S,3R,4R,7R,9R,11R,15S,16S,17R,18S,19Z,21Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
• IUPAC传统名: (1S,3R,4R,7R,9R,11R,15S,16S,17R,18S,19Z,21Z,25Z,27Z,29Z,31Z,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
• 别名: Fungicidin; Mycostatin; Nystatin; Nystatin Suspension

登记号

• CAS号: 1400-61-9
• EC号: 215-749-0
• PubChem SID: 162226090; 24897511; 24897647
• PubChem CID: 71308475

理论计算性质

• Acid pKa: 3.611593
• 质子受体: 17
• 质子供体: 12
• LogD (pH = 5.5): -1.9412671
• LogD (pH = 7.4): -1.9444739
• Log P: -1.9383262
• 摩尔折射率: 243.5539 cm^3
• 极化性: 94.91027 Å^3
• 极化表面积: 319.61 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: yellow suspension

安全信息

• RTECS编号: RF5950000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 浓度: 10,000 unit/mL in DPBS
• 适用性: suitable for cell culture
• 杂质: endotoxin, tested
• 无菌消毒: aseptically processed
• 产品质量级别: PREMIUM
• 运输包装: dry ice

详细说明

Sigma Aldrich - N3503

Biochem/physiol Actions
Mode of Action: Increases the permeability of the cell membrane of sensitive fungi by binding to sterols.Antimicrobial spectrum: Yeasts and molds.
Nystatin binds to ergosterol in fungal cell membranes which causes the formation of pores in the membrane. Potassium and other cellular constituents leak from the pores causing cell death. Antimicrobial spectrum: Yeasts and molds.
Application
Product N3503 is ≥4,400 USP units/mg. Nystatin is a polyene, antifungal antibiotic with potent proinflammatory properties. It has many applications such as preventing cell culture contamination and inducing interleukin (IL)-, IL-8, and tumor necrosis factor α s secretion in TLR2-expressing THP1 cells 1. It is used as a fungal membrane (ergosterol binding) pore forming agent and to create nystatin/ergosterol based ion channels in lipid bilayers.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - N1638

Application
Recommended for use in cell culture applications at 24 ml/L. Used as a fungal membrane (ergosterol binding) pore forming agent and to create nystatin/ergosterol based ion channels in lipid bilayers and as a lipid raft-inhibiting reagent and membrane associated cholesterol aggregator.
Biochem/physiol Actions
Mode of Action: Increases the permeability of the cell membrane of sensitive fungi by binding to sterols.Antimicrobial spectrum: Yeasts and molds.
Caution
Stable at 37 °C for 3 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information