(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

• ChemBase编号: 45
• 分子式: C20H30O2
• 平均质量: 302.451
• 单一同位素质量: 302.2245802
• SMILES: OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC
• Canonical SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
• InChI: InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
• InChIKey: JAZBEHYOTPTENJ-JLNKQSITSA-N

名称和登记号

名称

• IUPAC标准名: (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
• IUPAC传统名: eicosapentaenoic acid; icosapent
• 别名: 二十碳五烯酸; 顺式-5,8,11,14,17-二十碳五烯酸; (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic Acid; (all-Z)-5,8,11,14,17-Eicosapentaenoic Acid; EPA 45G; Icosapent; Incromega E 7010SR; Ropufa 70; Eicosapentaenoic Acid; cis-5,8,11,14,17-Eicosapentaenoic acid; Eicosapentaenoic acid; EPA; Icosapentaenoic acid; Timnodonic acid; Icosapent

登记号

• CAS号: 10417-94-4
• MDL号: MFCD00065716
• Beilstein号: 1714433
• PubChem SID: 24894450; 46506267; 24868422; 160963508; 24894640
• PubChem CID: 446284

理论计算性质

JChem

• Acid pKa: 4.819772
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 5.4632735
• LogD (pH = 7.4): 3.6901412
• Log P: 6.2252493
• 摩尔折射率: 101.0706 cm^3
• 极化性: 36.914207 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 6.53
• LOG S: -6.02
• 溶解度: 2.89e-04 g/l

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: Colorless Oil; liquid
• 熔点: -54--53 °C(lit.)
• 闪点: 199.4 °F; 93 °C
• 密度: 0.943 g/mL at 25 °C(lit.)
• 折射率: n20/D 1.4977(lit.)
• 疏水性(logP): 6.1

安全信息

• 保存条件: -20°C Freezer
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3265
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 34
• 安全公开号: 26-36/37/39-45
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314
• GHS警示性声明: P280-P305 + P351 + P338-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 3
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... ALOX5(240)mouse ... ALOX5(11689), Pparg(19016)rat ... ALOX5(25290); mouse ... Pparg(19016)

产品相关信息

• 纯度: ≥85%; ≥97.0% (GC); ≥98.5% (GC); ≥99%
• 级别: analytical standard; purum
• 有效期: (limited shelf life, expiry date on the label)
• 线性分子式: CH3(CH2CH=CH)5(CH2)3CO2H

详细说明

DrugBank - DB00159

• Drug Groups: approved; nutraceutical
• Description: Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. [PubChem]
• Indication: EPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.
• Pharmacology: Eicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.
• Affected Organisms: Humans and other mammals
• External Links: PDRhealth

Sigma Aldrich - E7006

Biochem/physiol Actions
5-脂氧合酶抑制剂；减少凝血噁烷 A2 生成。
包装
5, 10, 25, 50 mg in ampule
Sealed ampule.

Sigma Aldrich - E2011

Biochem/physiol Actions
5-脂氧合酶抑制剂；减少凝血噁烷 A2 生成。

Sigma Aldrich - 44864

Biochem/physiol Actions
5-脂氧合酶抑制剂；减少凝血噁烷 A2 生成。

Sigma Aldrich - 44865

Biochem/physiol Actions
5-脂氧合酶抑制剂；减少凝血噁烷 A2 生成。

Toronto Research Chemicals - E477800

Important polyunsaturated fatty acid of the marine food chain that serves as a precursor for the prostaglandin-3 and thromboxane-3 families. It differs from arachidonic acid (the eicosatetraenoic acid that is a precursor for the prostaglandin and thrombox

参考文献

• Bergstrom, S., et al.: J. Biol. Chem., 239, PC 4006 (1964)
• Srivastava, K.C., et al.: Biochem. Exp. Biol., 16, 317 (1964)
• Kremer, J.M., et al.: Ann. Intern. Med., 106, 497 (1964)
• DiGiacomo, R.A., et al.: Am. J. Med., 86, 158 (1964)