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

• ChemBase编号: 158418
• 分子式: C20H32O5
• 平均质量: 352.46508
• 单一同位素质量: 352.22497412
• SMILES: CCCCC[C@@H](C=C[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C/CCCC(=O)O)O)O
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C/CCCC(=O)O)O
• InChI: InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1
• InChIKey: XEYBRNLFEZDVAW-DODZYUBVSA-N

名称和登记号

名称

• IUPAC标准名: 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
• IUPAC传统名: 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
• 别名: (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid; Dinoprostone; PGE2; Prostaglandin E2

登记号

• CAS号: 363-24-6
• EC号: 206-656-6
• MDL号: MFCD00077861
• Beilstein号: 4709356
• PubChem SID: 162252554
• PubChem CID: 49822699

理论计算性质

• Acid pKa: 4.3033595
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 2.0038702
• LogD (pH = 7.4): 0.2647247
• Log P: 3.22527
• 摩尔折射率: 99.4351 cm^3
• 极化性: 38.188305 Å^3
• 极化表面积: 94.83 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: acetone: soluble10 mg/mL, clear, colorless to faintly yellow

安全信息

• RTECS编号: UK8000000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 60-61-22
• 安全公开号: 53-22-26-36/37/39-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H360
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 保存温度: -20°C

产品相关信息

• 纯度: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C20H32O5

详细说明

Sigma Aldrich - 82475

Other Notes
Differential effect of PGE2 on transforming growth factor-β, and insulin-induced collagen formation in lung fibroblasts2
Biochem/physiol Actions
Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.1