{5-[(1S,2S)-2-[(3S,6S,9S,11R,18S,20R,21R,24S,25S,26S)-3-[(1R)-2-carbamoyl-1-hydroxyethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-(4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzamido)-1,4,7,13,16,22-hexaazatricyclo[22.3.0.09,13]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid

• ChemBase编号: 174615
• 分子式: C56H71N9O23S
• 平均质量: 1270.27444
• 单一同位素质量: 1269.43835058
• SMILES: O[C@@H]([C@H]1C(=O)N[C@H](C(=O)N2C[C@@H]([C@@H]([C@H]2C(=O)N[C@@H]([C@@H](C[C@H](C(=O)NC(C(=O)N2[C@H](C(=O)N1)C[C@H](C2)O)[C@H](O)C)NC(=O)c1ccc(cc1)c1noc(c1)c1ccc(cc1)OCCCCC)O)O)O)C)[C@@H](CC(=O)N)O)[C@@H](O)c1cc(c(cc1)O)OS(=O)(=O)O
• Canonical SMILES: CCCCCOc1ccc(cc1)c1onc(c1)c1ccc(cc1)C(=O)N[C@@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@H](CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)C(NC1=O)[C@H](O)C)C[C@@H](C2)O)[C@@H]([C@H](c1ccc(c(c1)OS(=O)(=O)O)O)O)O)[C@@H](CC(=O)N)O)C
• InChI: InChI=1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26+,31+,34-,35-,37+,38+,42?,43-,44-,45-,46-,47-,48-,52+/m0/s1
• InChIKey: PIEUQSKUWLMALL-SICPAZHLSA-N

名称和登记号

名称

• IUPAC标准名: {5-[(1S,2S)-2-[(3S,6S,9S,11R,18S,20R,21R,24S,25S,26S)-3-[(1R)-2-carbamoyl-1-hydroxyethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-(4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzamido)-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^9,^1^3]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid
• IUPAC传统名: {5-[(1S,2S)-2-[(3S,6S,9S,11R,18S,20R,21R,24S,25S,26S)-3-[(1R)-2-carbamoyl-1-hydroxyethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-(4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzamido)-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^9,^1^3]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid
• 别名: 1-[(4R,5R)-4,5-Dihydroxy-N2-[4-[5-[4-(pentyloxy)phenyl]-3-isoxazolyl]benzoyl]-L-ornithine]-4-[(4S)-4-hydroxy-4-[4-hydroxy-3-(sulfooxy)phenyl]-L-threonine]pneumocandin A0 Monosodium Salt; Funguard; FK 463; Micafungin Sodium

登记号

• CAS号: 208538-73-2
• PubChem SID: 164230525
• PubChem CID: 44449748

理论计算性质

• Acid pKa: -2.1882572
• 质子受体: 22
• 质子供体: 16
• LogD (pH = 5.5): -6.740862
• LogD (pH = 7.4): -6.7417994
• Log P: -6.3384485
• 摩尔折射率: 303.071 cm^3
• 极化性: 121.588326 Å^3
• 极化表面积: 510.14 Å^2
• 可自由旋转的化学键: 18
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Water
• 外观: Off-White Solid
• 熔点: >211°C (dec.)

详细说明

Toronto Research Chemicals - M342350

An echinocandin antifungal drug which inhibits the synthesis of 1,3-β-D-glucan, an essential component of the fungal cell wall, and represent a valuable treatment option for fungal infections.

参考文献

• Chen, S.C. et al.: Drugs, 71, 11 (2011)
• Groll, A.H. et al.: Opin. Anti-Infect. Invest. Drugs, 2, 405 (2011)
• Tomishima, M. et al.: J. Antibiot., 52, 674 (2011)