ethyl 2-(3,5-dihydroxy-2-octanoylphenyl)acetate

• ChemBase编号: 154144
• 分子式: C18H26O5
• 平均质量: 322.39604
• 单一同位素质量: 322.17802393
• SMILES: CCCCCCCC(=O)c1c(cc(cc1O)O)CC(=O)OCC
• Canonical SMILES: CCCCCCCC(=O)c1c(O)cc(cc1CC(=O)OCC)O
• InChI: InChI=1S/C18H26O5/c1-3-5-6-7-8-9-15(20)18-13(11-17(22)23-4-2)10-14(19)12-16(18)21/h10,12,19,21H,3-9,11H2,1-2H3
• InChIKey: UVVWQQKSNZLUQA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl 2-(3,5-dihydroxy-2-octanoylphenyl)acetate
• IUPAC传统名: ethyl 2-(3,5-dihydroxy-2-octanoylphenyl)acetate
• 别名: 3,5-Dihydroxy-2-(1-oxooctyl)benzeneacetic acid ethyl ester; Csn-B; 3,5-Dihydroxy-2-(1-oxooctyl)-benzeneacetic acid, ethyl ester; Csn-B; Cytosporone B

登记号

• CAS号: 321661-62-5
• MDL号: MFCD12912406
• PubChem SID: 162248283
• PubChem CID: 10687292

理论计算性质

• Acid pKa: 7.80963
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 4.6354833
• LogD (pH = 7.4): 4.4958935
• Log P: 4.6375923
• 摩尔折射率: 88.8798 cm^3
• 极化性: 34.463524 Å^3
• 极化表面积: 83.83 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL
• 外观: white to off-white

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: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H26O5

详细说明

Sigma Aldrich - C2997

Biochem/physiol Actions
Cytosporone B (Csn-B) is the first naturally occurring agonist for nuclear orphan receptor Nur77. It binds with high affinity (IC50=0.278 nM) to the ligand-binding domain of Nur77 and stimulates Nur77-dependent activities. Nur77 is a nuclear receptor/transcription factor. A physiological ligand for Nur77 is as yet unknown, but there is increasing interest in Nur77 because of its known activities. Translocation of Nur77 from the nucleus to mitochondria initiates cell apoptosis, making it a potential target for cancer treatment. Nur77 is also involved in glucose homeostasis; it induces genes involved in gluconeogenesis. Csn-B physically binds to Nur77 and activates its transactivational activity and translocation to mitochondria to induce apoptosis. It inhibits cancer cell proliferation and tumor growth.
Cytosporone B is a fungal metabolite closely related to phomposin C. It is the first known agonist for the nuclear orphan receptor Nur77. It binds with high affinity (IC50 = 0.278 nM) to the ligand-binding domain of Nur77 and stimulates Nur77-dependent activities.Nur77 is a nuclear receptor/transcription factor with no known physiological ligand, but there is increasing interest in Nur77 because of its known activities. Translocation of Nur77 from the nucleus to mitochondria initiates apoptosis, making it a potential target for cancer chemotherapy. Nur77 also induces genes involved in gluconeogenesis. Csn-B activates the Nur77 translocation to mitochondria to induce apoptosis, inhibiting cancer cell proliferation and tumor growth.