methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(2R,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-carboxylate

• ChemBase编号: 160589
• 分子式: C48H75NO17
• 平均质量: 938.1056
• 单一同位素质量: 937.50349995
• SMILES: C\1=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)O[C@H]([C@@H]([C@@H]([C@H]1C)O)C)C)O)O)O)O)O)(O)O2)O)C(=O)OC)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)C)O)N)O
• Canonical SMILES: COC(=O)[C@H]1[C@@H]2C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@H]([C@H]([C@@H](OC(=O)C[C@@H](C[C@@H](CC[C@H]([C@@H](C[C@@H](C[C@@](O2)(C[C@@H]1O)O)O)O)O)O)O)C)C)O)O[C@@H]1O[C@H](C)[C@H]([C@H]([C@@H]1O)N)O
• InChI: InChI=1S/C48H75NO17/c1-28-18-16-14-12-10-8-6-7-9-11-13-15-17-19-35(65-47-45(59)42(49)44(58)31(4)64-47)25-39-41(46(60)62-5)38(55)27-48(61,66-39)26-34(52)23-37(54)36(53)21-20-32(50)22-33(51)24-40(56)63-30(3)29(2)43(28)57/h6-19,28-39,41-45,47,50-55,57-59,61H,20-27,49H2,1-5H3/b7-6+,10-8+,11-9+,14-12+,15-13+,18-16+,19-17+/t28-,29-,30-,31+,32+,33+,34-,35-,36+,37+,38-,39?,41+,42-,43+,44+,45-,47-,48+/m0/s1
• InChIKey: UAZIZEMIKKIBCA-SROBOZQESA-N

名称和登记号

名称

• IUPAC标准名: methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(2R,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-carboxylate
• IUPAC传统名: amphotericin B methyl ester
• 别名: Amphotericin B Monomethyl Ester; Amphotericin B Methyl Ester 90%

登记号

• CAS号: 36148-89-7
• PubChem SID: 162254724
• PubChem CID: 11968030

理论计算性质

• Acid pKa: 11.823185
• 质子受体: 16
• 质子供体: 11
• LogD (pH = 5.5): -2.8226233
• LogD (pH = 7.4): -1.5940475
• Log P: 0.1097699
• 摩尔折射率: 249.4396 cm^3
• 极化性: 96.73872 Å^3
• 极化表面积: 308.61 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Yellow Solid
• 熔点: >175°C (dec.)

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - A634255

Amphotericin B Methyl Ester is the methyl ester derivative of the polyene antibiotic Amphotericin B (A634250). Amphotericin B Methyl Esterin is a cholesterol binding compound that showed inhibiton of human immunodeficiency virus type 1 (HIV-1).

参考文献

• Waheed, A.A. et al.: J. Biol. Chem., 281, 28699 (2006)
• Waheed, A. et al.: J. Virol., 82, 9776 (2006)