(2E)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid

• ChemBase编号: 155599
• 分子式: C22H36O5
• 平均质量: 380.51824
• 单一同位素质量: 380.25627425
• SMILES: CCCC[C@H](C)C[C@@H](C=C[C@H]1[C@@H](CC(=O)[C@@H]1CCCC/C=C/C(=O)O)O)O
• Canonical SMILES: CCCC[C@@H](C[C@@H](C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCC/C=C/C(=O)O)O)C
• InChI: InChI=1S/C22H36O5/c1-3-4-9-16(2)14-17(23)12-13-19-18(20(24)15-21(19)25)10-7-5-6-8-11-22(26)27/h8,11-13,16-19,21,23,25H,3-7,9-10,14-15H2,1-2H3,(H,26,27)/t16-,17+,18+,19+,21+/m0/s1
• InChIKey: OJZYRQPMEIEQFC-HMPZBHLVSA-N

名称和登记号

名称

• IUPAC标准名: (2E)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid; 7-[(1R,2R,3R)-3-hydroxy-2-[(3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid
• IUPAC传统名: limaprost; 7-[(1R,2R,3R)-3-hydroxy-2-[(3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid
• 别名: (2E)-7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl]-2-heptenoic Acid; (2E,11α,13E,15S,17S)-11,15-Dihydroxy-17,20-dimethyl-9-oxo-prosta-2,13-dien-1-oic Acid; 17S,20-Dimethyl-trans-Δ2-PGE1; ONO 1206; OP 1206; Limaprost; 11α,15S-Dihydroxy-17S,20-dimethyl-9-oxo-prosta-2E,13E-dien-1-oic acid; 17α,20-dimethyl-δ2-PGE1; Limaprost

登记号

• CAS号: 74397-12-9
• MDL号: MFCD00868275
• PubChem SID: 162249737
• PubChem CID: 71312166

理论计算性质

• Acid pKa: 4.4431877
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 3.2247262
• LogD (pH = 7.4): 1.4622635
• Log P: 4.316603
• 摩尔折射率: 108.5614 cm^3
• 极化性: 41.864788 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: DMF: soluble; DMSO: soluble; ethanol: soluble
• 外观: crystalline

安全信息

• RTECS编号: UK8362500
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 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): 2
• 危险公开号: 25
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ≥99%
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C22H36O5

详细说明

Sigma Aldrich - L6538

Other Notes
Potent analog of PGE1 with prolonged half-life.

Toronto Research Chemicals - L461500

Limaprost is an analog of Prostaglandin E1 with structural modifications intended to give it a prolonged half-life and greater potency. Limaprost is used as an antianginal.

参考文献

• Tsuboi, T., et al.: Arch. Int. Pharmacodyn., 247, 89 (1980)
• Adaikan, P.G., et al.: Prostaglandins Med., 6, 449 (1980)
• Kottegoda, S.R., et al.: Prostaglandins Leukotrienes Med., 8, 343 (1980)
• Ishizaki, T., et al.: Chest, 85, 382 (1980)