sodium 5-[(3E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-3-ylidene]pentanoate

• ChemBase编号: 133752
• 分子式: C20H31NaO5
• 平均质量: 374.44691
• 单一同位素质量: 374.20691837
• SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1/C(=C\CCCC(=O)[O-])/CO2)O)O.[Na+]
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1/C(=C\CCCC(=O)[O-])/CO2)O.[Na+]
• InChI: InChI=1S/C20H32O5.Na/c1-2-3-4-8-15(21)10-11-16-17(22)12-18-20(16)14(13-25-18)7-5-6-9-19(23)24;/h7,10-11,15-18,20-22H,2-6,8-9,12-13H2,1H3,(H,23,24);/q;+1/p-1/b11-10+,14-7-;/t15-,16-,17+,18-,20+;/m0./s1
• InChIKey: OURCVRVJQMLUNA-QFDVFERUSA-M

名称和登记号

名称

• IUPAC标准名: sodium 5-[(3E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-3-ylidene]pentanoate
• IUPAC传统名: sodium 5-[(3E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydrocyclopenta[b]furan-3-ylidene]pentanoate
• 别名: Epoprostenol 钠; (5Z,9α,11α,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid sodium salt; PGI2-Na; Prostacyclin sodium salt; Prostaglandin I2 sodium salt

登记号

• CAS号: 61849-14-7
• EC号: 263-273-7
• MDL号: MFCD00135629
• Beilstein号: 6472195
• PubChem SID: 162228029; 24898653
• PubChem CID: 23702145

理论计算性质

• Acid pKa: 4.398562
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 1.1578689
• LogD (pH = 7.4): -0.59833145
• Log P: 2.2907794
• 摩尔折射率: 109.2534 cm^3
• 极化性: 37.96977 Å^3
• 极化表面积: 89.82 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: ethanol: soluble50 mg/mL; H2O: soluble1 mg/mL (Hydrolyzes to 6-ketoprostaglandin F1α in aqueous solution.)
• 外观: white to off-white powder

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22
• 安全公开号: 22-26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 纯度: ≥96% (HPLC)
• 生物来源: synthetic

详细说明

Sigma Aldrich - P6188

Biochem/physiol Actions
Prostacyclin is a short-lived product of the cyclooxygenase pathway in vascular endothelial cells. It is a potent inhibitor of platelet aggregation by antagonizing thromboxane A2 and stimulating platelet adenylyl cyclase.1 Nitric oxide is also produced in vascular endothelium where it inhibits platelet aggregation, regulates inducible cyclooxygenase production, and may work synergistically with prostacyclin to attenuate the thrombotic process. Prostacyclin is vasoprotective, protecting arterial walls from injury-induced lesions and cytoprotective in the liver and gastrointestinal tract.
Prostacyclin therapy improves hemodynamics in pulmonary arterial hypertension.