(3S,6S,15aR)-9-(butan-2-yl)-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)-tetradecahydro-1H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

• ChemBase编号: 154207
• 分子式: C34H49N5O6
• 平均质量: 623.78276
• 单一同位素质量: 623.36828431
• SMILES: CCC(C)C1C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)Cc1cn(c2c1cccc2)OC)CCCCCC(=O)CC
• Canonical SMILES: CCC(=O)CCCCC[C@@H]1NC(=O)[C@H]2CCCCN2C(=O)C(NC(=O)[C@@H](NC1=O)Cc1cn(c2c1cccc2)OC)C(CC)C
• InChI: InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22?,26-,27-,29+,30?/m0/s1
• InChIKey: JWOGUUIOCYMBPV-PYAAAQPJSA-N

名称和登记号

名称

• IUPAC标准名: (3S,6S,15aR)-9-(butan-2-yl)-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)-tetradecahydro-1H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• IUPAC传统名: (3S,6S,15aR)-6-[(1-methoxyindol-3-yl)methyl]-3-(6-oxooctyl)-9-(sec-butyl)-decahydro-2H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• 别名: Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]; Apicidin

登记号

• CAS号: 183506-66-3
• MDL号: MFCD03452661
• PubChem SID: 162248346
• PubChem CID: 57568978

理论计算性质

• Acid pKa: 10.834099
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): 3.374681
• LogD (pH = 7.4): 3.3745413
• Log P: 3.374683
• 摩尔折射率: 171.2108 cm^3
• 极化性: 67.55282 Å^3
• 极化表面积: 138.84 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: acetonitrile: ~1 mg/mL; DMSO: ~1 mg/mL
• 外观: solid

安全信息

• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 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): 2
• 危险公开号: 26/27/28
• 安全公开号: 22-26-36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330
• GHS警示性声明: P260-P264-P280-P284-P302 + P350-P310
• 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
• RID/ADR: UN 2811 6.1/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 生物来源: from microbial
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C34H49N5O6

详细说明

Sigma Aldrich - A8851

Biochem/physiol Actions
Potent (nM) cell permeable inhibitor of histone deacetylase. Also, exhibits antiprotozoal and potential antimalarial properties. Apicidin has antiproliferative activity on HeLa cells accompanied by cell arrest at the G1 phase. In addition, it induces selective changes in the expression of p21 and gelsolin.