(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid

• ChemBase编号: 72773
• 分子式: C47H73NO17
• 平均质量: 924.07902
• 单一同位素质量: 923.48784988
• SMILES: [C@@H]1([C@H](C)[C@@H]([C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@@](C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O1)O)O)O)O)O)(O2)O)O)C(=O)O)OC1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)O)C)O)C
• Canonical SMILES: O[C@@H]1CC[C@@H](O)[C@H](O)C[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/C=C/C=C/C=C/[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C1)O)C)C)O)C)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=O)O
• InChI: InChI=1S/C47H73NO17/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)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,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: APKFDSVGJQXUKY-QSSPICSASA-N

名称和登记号

名称

• IUPAC标准名: (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
• IUPAC传统名: (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
• 别名: Amphotericin B; Fungilin; Fungizone; AmBisome; Fungisome

登记号

• CAS号: 1397-89-3
• PubChem SID: 162037694
• PubChem CID: 9919339

理论计算性质

• 质子受体: 17
• 质子供体: 12
• LogD (pH = 5.5): -2.3028812
• LogD (pH = 7.4): -2.3064086
• Log P: -2.3001616
• 摩尔折射率: 244.6705 cm^3
• 极化性: 94.662575 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
• Acid pKa: 3.5797393

分子性质

理化性质

• 溶解度: DMSO

安全信息

• 保存条件: -20°C

产品相关信息

• 成盐信息: Free Base

详细说明

Selleck Chemicals - S1636

Research Area: Infection
Biological Activity:
Amphotericin B is a polyene, antifungal antibiotic produced from a strain of Streptomyces nodosus. (IC50=0.028–0.290 μg/ml) [1] It has been the most effective systemic antifungal agent. [2] For Histoplasma and Blastomyces infections the mean effective dose (ED50) of amphotericin B was 0.3 mg/kg, whereas the corresponding values for AME, respectively, were 2.4 and 2.8 mg/kg. For Cryptococcus infection the ED50 for amphotericin B was 0.2 mg/kg compared with 2.0 mg/kg for AME. The ED50 of amphotericin B for Candida infection was lower than 0.05 mg/kg and the value of AME was between 0.5 to 0.05 mg/kg. [3]

参考文献

• Kayser O et al. Acta Trop. 2003 Apr;86(1):105-7.