(3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1,11-dioxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

• ChemBase编号: 126841
• 分子式: C30H37NO6
• 平均质量: 507.61788
• 单一同位素质量: 507.26208791
• SMILES: C[C@@H]1CC=C[C@@H]2[C@@H](C(=C)[C@H]([C@@H]3[C@@]2([C@@H](C=C[C@@](C1=O)(C)O)OC(=O)C)C(=O)N[C@H]3Cc1ccccc1)C)O
• Canonical SMILES: CC(=O)O[C@@H]1C=C[C@@](C)(O)C(=O)[C@@H](CC=C[C@H]2[C@]31C(=O)N[C@H]([C@@H]3[C@H](C)C(=C)[C@H]2O)Cc1ccccc1)C
• InChI: InChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/t17-,18+,22-,23-,24+,25-,26+,29+,30+/m0/s1
• InChIKey: SDZRWUKZFQQKKV-DIPXFXJQSA-N

名称和登记号

名称

• IUPAC标准名: (3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1,11-dioxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate
• IUPAC传统名: cytochalasin D
• 别名: 松胞菌素 D; 细胞松弛素 D; Zygosporin A; Cytohalasin D; Lygosporin A; Cytochalasin D; Cytochalasin D

登记号

• CAS号: 22144-77-0
• EC号: 244-804-1
• MDL号: MFCD00077706
• Beilstein号: 1632828
• PubChem SID: 162221168
• PubChem CID: 5458428; 71308181
• Chemspider ID: 16736231
• 维基百科标题: Cytochalasin_D

理论计算性质

• Acid pKa: 12.848232
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 3.1152396
• LogD (pH = 7.4): 3.1152387
• Log P: 3.1152403
• 摩尔折射率: 141.5228 cm^3
• 极化性: 54.907993 Å^3
• 极化表面积: 112.93 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 闪点: 188.6 °F; 87 °C

安全信息

• RTECS编号: GZ4850000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 1544
• 德国WGK号: 2; 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: 63-25
• 安全公开号: 36/37-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H300-H361
• GHS警示性声明: P264-P281-P301 + 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; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1544 6.1/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ≥99.0% (TLC)
• 浓度: 5 mg/mL in DMSO
• 生物来源: from Zygosporium mansonii
• 无菌消毒: 0.2 μm filtered
• 产品质量级别: PREMIUM
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C30H37NO6

详细说明

Sigma Aldrich - C2618

Biochem/physiol Actions
肌动蛋白聚合化的强效抑制剂；破坏肌动蛋白微丝；活化 p53 依赖性途径；抑制平滑肌收缩；抑制胰岛素刺激的糖转运。
Cell permeable fungal toxin; potent inhibitor of actin polymerization. Disrupts actin microfilaments and activates the p53-dependent pathways causing arrest of the cell cycle at the G1-S transition. Inhibits smooth muscle contraction. Inhibits insulin-stimulated, but not basal, transport of glucose.
Cytochalasin B is a cell permeable fungal toxin and potent inhibitor of actin polymerization. It disrupts actin microfilaments and activates the p53-dependent pathways causing arrest of the cell cycle at the G1-S transition. It inhibits smooth muscle contraction and insulin-stimulated, but not basal, transport of glucose.
Application
Cytochalasin B is used to inhibit sugar transport in fibroblasts 1, decrease cytoskeletal actin and myosin in rabbit neutrophils 2, and to stimulate B lymphocytes 3. It is a potent inhibitor of actin polymerization, disrupts actin microfilaments, activates the p53-dependent pathways, inhibits smooth muscle contraction, and inhibits insulin-stimulated glucose transport.

Sigma Aldrich - 859958

Biochem/physiol Actions
肌动蛋白聚合化的强效抑制剂；破坏肌动蛋白微丝；活化 p53 依赖性途径；抑制平滑肌收缩；抑制胰岛素刺激的糖转运。

Sigma Aldrich - 30385

Biochem/physiol Actions
肌动蛋白聚合化的强效抑制剂；破坏肌动蛋白微丝；活化 p53 依赖性途径；抑制平滑肌收缩；抑制胰岛素刺激的糖转运。