7-[(1R,2R,3R)-3-hydroxy-2-(4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl]heptanoic acid

• ChemBase编号: 155178
• 分子式: C21H36O5
• 平均质量: 368.50754
• 单一同位素质量: 368.25627425
• SMILES: CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
• Canonical SMILES: CCCCC(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)(O)C
• InChI: InChI=1S/C21H36O5/c1-3-4-13-21(2,26)14-9-11-17-16(18(22)15-19(17)23)10-7-5-6-8-12-20(24)25/h9,11,16-17,19,23,26H,3-8,10,12-15H2,1-2H3,(H,24,25)/t16-,17-,19-,21?/m1/s1
• InChIKey: CNWGPXZGIIOYDL-AOJMRFDNSA-N

名称和登记号

名称

• IUPAC标准名: 7-[(1R,2R,3R)-3-hydroxy-2-(4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl]heptanoic acid; 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
• IUPAC传统名: 7-[(1R,2R,3R)-3-hydroxy-2-(4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl]heptanoic acid; 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
• 别名: (±)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1; Misoprostol free acid; (11α,13E)-(+/-)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic Acid Methyl Ester; Cytotec; Misogon; Misoprostil; SC 29333; Misoprostol Acid, Technical Grade 65%DISCONTINUED. See M368760; (11α,13E)-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oic Acid; Misoprostol Free Acid; (+/-)-15-Deoxy-(16RS)-16-hydroxy-16-methylprogestaglandin E1; Misoprostol Acid (10 mg in 1 mL Methyl Acetate)

登记号

• CAS号: 112137-89-0
• MDL号: MFCD00869984
• PubChem SID: 24897131; 162249316
• PubChem CID: 6436406

理论计算性质

• Acid pKa: 4.353234
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 2.5369675
• LogD (pH = 7.4): 0.7882538
• Log P: 3.711861
• 摩尔折射率: 103.1107 cm^3
• 极化性: 40.270283 Å^3
• 极化表面积: 94.83 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol; Methyl Acetate
• 外观: Clear Colorless solution; Pale Yellow Gel

安全信息

• 保存条件: -20°C Freezer; -86?C Freezer
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2810
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 60-61-25-36/37/38
• 安全公开号: 53-26-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335-H361
• GHS警示性声明: P261-P281-P301 + P310-P305 + P351 + P338
• RID/ADR: UN 2810 6.1/PG 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥90%
• Empirical Formula (Hill Notation): C21H36O5

详细说明

Sigma Aldrich - M6932

Biochem/physiol Actions
Cytoprotective PGE1 analog that prevents NSAID-induced gastric ulceration.

Toronto Research Chemicals - M368760

A metabolite of Misoprostol. Cytoprotective PGE1 analog that prevents NSAID-induced gastric ulceration.

Toronto Research Chemicals - M368761

A cytoprotective prostaglandin PGE1 analogue.

参考文献

• Graham, Y., et al.: Lancet, 2, 1277 (1988)
• 11) Garris, R., et al.: Clin. Pharmacol., 8, 627 (1988)
• Karim, A., et al.: J. Clin. Pharmacol., 29, 439 (1988)
• Graham, Y., et al.: Lancet, 2, 1277 (1988)
• Graham, D.Y., et al.: Ann. Int. Med., 119, 257 (1988)
• Fletcher, H., et al.: Obstet. Gynecol., 83, 244 (1994)