(1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one

• ChemBase编号: 132479
• 分子式: C16H24O4
• 平均质量: 280.35936
• 单一同位素质量: 280.16745925
• SMILES: C[C@H]1CCC/C=C\[C@@H]2C[C@@H](C[C@H]2[C@@H](/C=C\C(=O)O1)O)O
• Canonical SMILES: O[C@@H]1C[C@@H]2[C@@H](C1)/C=C\CCC[C@@H](OC(=O)/C=C\[C@H]2O)C
• InChI: InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4-,8-7-/t11-,12+,13-,14+,15+/m0/s1
• InChIKey: KQNZDYYTLMIZCT-QJNJASIYSA-N

名称和登记号

名称

• IUPAC标准名: (1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one
• IUPAC传统名: brefeldin A
• 别名: γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone; Ascotoxin; BFA; Cyanein; Decumbin; Brefeldin A

登记号

• CAS号: 20350-15-6
• MDL号: MFCD12913297
• Beilstein号: 25191
• PubChem SID: 24278285; 162226756; 24891917
• PubChem CID: 24123450

理论计算性质

• Acid pKa: 14.419293
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 2.007216
• LogD (pH = 7.4): 2.007216
• Log P: 2.007216
• 摩尔折射率: 78.7488 cm^3
• 极化性: 30.270922 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: ethanol: soluble1-5 mg/mL (Store stock solutions at -20 °C.); methanol: soluble10 mg/mL (Store stock solutions at -20 °C.)

安全信息

• RTECS编号: GY8410000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 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): 3
• 危险公开号: 22
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥99% (HPLC and TLC)
• 级别: for molecular biology
• 生物来源: from Penicillium brefeldianum
• 产品质量级别: PREMIUM

详细说明

Sigma Aldrich - B6542

Analysis Note
Tested for inhibition of interleukin export from Jurkat cells.
Biochem/physiol Actions
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.

Sigma Aldrich - B7651

Biochem/physiol Actions
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.