5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoic acid

• ChemBase编号: 171527
• 分子式: C22H32O4
• 平均质量: 360.48708
• 单一同位素质量: 360.2300595
• SMILES: [C@@H]1([C@@H]([C@@H]2[C@H](C1)C/C(=C\CCCC(=O)O)/C2)/C=C/[C@H](C(CC#CC)C)O)O
• Canonical SMILES: CC#CCC([C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)C
• InChI: InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1
• InChIKey: HIFJCPQKFCZDDL-ACWOEMLNSA-N

名称和登记号

名称

• IUPAC标准名: 5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoic acid
• IUPAC传统名: iloprostum
• 别名: (5E)-5-[(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-yn-1-yl]-2(1H)-pentalenylidene]pentanoic Acid; (1S,2R,3R,5S)-7-[(E)-4-Carboxybutylidene]-2-[(3S,1E)-3-hydroxy-4-methyl-6-octyn-1-enyl]-bicyclo[3.3.0]octane; Ciloprost; Endoprost; Ilomedin; ZK 36374; Iloprost

登记号

• CAS号: 78919-13-8
• PubChem SID: 164227437
• PubChem CID: 5311181

理论计算性质

• Acid pKa: 4.664816
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 2.6708264
• LogD (pH = 7.4): 0.8930734
• Log P: 3.5643785
• 摩尔折射率: 105.1822 cm^3
• 极化性: 39.96046 Å^3
• 极化表面积: 77.76 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - I267300

A synthetic analogue of Prostacyclin (PGI2) used to treat pulmonary arterial hypertension (PAH), scleroderma, Raynaud's phenomenon and ischemia. It acts through elevation of cAMP by binding to the prostacyclin receptor (IP receptor). Iloprost inhibits the

参考文献

• Zamudio, T.P.: Arch. Cardiol. Mex., 77, 198 (2007)
• Lai, Y. et al.: Am. J. Resp. Crit. Care Med., 178, 188 (2007)
• Scorza, R. et al.: J. Rheutamol., 24, 1944 (2007)
• Melillo, E. et al.: Int. J. Microcircul. Clin. Exp., 15, 60 (2007)