(2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxooctadec-16-en-3-yl]-4-methyl-2-(methylamino)pentanamide

• ChemBase编号: 165297
• 分子式: C29H55N3O4
• 平均质量: 509.7647
• 单一同位素质量: 509.41925726
• SMILES: C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)[C@@H]([C@@H](C/C=C/C)C)O
• Canonical SMILES: C/C=C/C[C@H]([C@H](C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)O)C
• InChI: InChI=1S/C29H55N3O4/c1-10-11-16-22(6)28(35)27(32(8)9)25(34)18-15-13-12-14-17-24(33)26(21(4)5)31-29(36)23(30-7)19-20(2)3/h10-11,20-23,26-28,30,35H,12-19H2,1-9H3,(H,31,36)/b11-10+/t22-,23+,26+,27?,28-/m1/s1
• InChIKey: OVRSPEVBEPEKGL-BGAWTGSHSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxooctadec-16-en-3-yl]-4-methyl-2-(methylamino)pentanamide
• IUPAC传统名: (2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxooctadec-16-en-3-yl]-4-methyl-2-(methylamino)pentanamide
• 别名: Cyclosporine; Ciclosporin; Atopica; Sandimmun(e); Neoral; Optimmune; Restasis; Cyclosporin A

登记号

• CAS号: 59865-13-3
• PubChem SID: 162259430
• PubChem CID: 71315116

理论计算性质

• Acid pKa: 13.089189
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): 0.9756581
• LogD (pH = 7.4): 3.7048545
• Log P: 5.410551
• 摩尔折射率: 149.4386 cm^3
• 极化性: 58.9265 Å^3
• 极化表面积: 98.74 Å^2
• 可自由旋转的化学键: 20
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Acetone; Chloroform; Ethanol
• 外观: White Solid
• 熔点: 148-151°C

安全信息

• 保存条件: Refrigerator

详细说明

Toronto Research Chemicals - C988900

An immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection.A group of nonpolar cyclic oligopeptides with immunosupppressant activity.

参考文献

• van Wartburg, A., et al.: Prog. Med. Chem., 25, 1 (1988)
• Jorgensen, K.A., et al.: Scand. J. Imunol., 57, 93 (1988)
• Vollenbroeker, et al.: Transplant. Proc., 37, 1741 (1988)