N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide

• ChemBase编号: 154314
• 分子式: C35H28N4O5
• 平均质量: 584.62062
• 单一同位素质量: 584.20597002
• SMILES: C[C@@]12[C@@H]([C@@H](C[C@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3c(=O)[nH]c1=O)N(C)C(=O)c1ccccc1)OC
• Canonical SMILES: CO[C@@H]1[C@@H](C[C@@H]2O[C@]1(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3c(=O)[nH]c1=O)N(C(=O)c1ccccc1)C
• InChI: InChI=1S/C35H28N4O5/c1-35-31(43-3)23(37(2)34(42)18-11-5-4-6-12-18)17-24(44-35)38-21-15-9-7-13-19(21)25-27-28(33(41)36-32(27)40)26-20-14-8-10-16-22(20)39(35)30(26)29(25)38/h4-16,23-24,31H,17H2,1-3H3,(H,36,40,41)/t23-,24+,31-,35+/m1/s1
• InChIKey: MQCCJEYZKWZQHU-JTPSWESPSA-N

名称和登记号

名称

• IUPAC标准名: N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^2,^6.0^7,^2^8.0^8,^1^3.0^1^5,^1^9.0^2^0,^2^7.0^2^1,^2^6]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide
• IUPAC传统名: N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^2,^6.0^7,^2^8.0^8,^1^3.0^1^5,^1^9.0^2^0,^2^7.0^2^1,^2^6]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide
• 别名: Stauprimide

登记号

• CAS号: 154589-96-5
• PubChem SID: 162248453
• PubChem CID: 71311840

理论计算性质

• Acid pKa: 8.031408
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 5.3271093
• LogD (pH = 7.4): 5.238331
• Log P: 5.3284235
• 摩尔折射率: 163.3356 cm^3
• 极化性: 66.67411 Å^3
• 极化表面积: 94.8 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

分子性质

理化性质

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

安全信息

• 德国WGK号: 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C35H28N4O5

详细说明

Sigma Aldrich - S2951

Biochem/physiol Actions
Stauprimide is an enhancer stem cell differentiation into endoderm. In vitro differentiation of embryonic stem cells is of great interest to regenerative medicine, and current protocols are labor-intensive and expensive. Small molecules that induce or enhance differentiation are highly desired. High-content screening identified compounds that enhance endodermal differentiation in the presence of low levels of Activin A. Stauprimide increased definitive endodermal markers but not markers for visceral/parietal endoderm or mesoderm. Stauprimide-differentiated cells could be further differentiated into hepatocytes. Stauprimide treatment during differentiation decreased the concentration of Activin A required for definitive endoderm formation, and it eliminated the need for serum. The mechanism of action of stauprimide is to sensitize cells for differentiation. Stauprimide enabled differentiation into other cell lineages under varying differentiation conditions, including neurons, hematopoietic mesoderm, beating cardiac myocytes, and skeletal muscle. The cellular target of stauprimide was determined to be inhibition of NME2 transcription factor translocation to the nucleus, leading to down-regulation of c-Myc expression.