(5R,9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione

• ChemBase编号: 133759
• 分子式: C29H37NO5
• 平均质量: 479.60778
• 单一同位素质量: 479.26717329
• SMILES: C[C@@H]1CCC[C@H](/C=C\C(=O)O[C@]23[C@@H](/C=C\C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)Cc1ccccc1)C)O)O
• Canonical SMILES: C[C@@H]1CCC[C@@H](O)/C=C\C(=O)O[C@@]23[C@@H](/C=C\C1)[C@H](O)C(=C)[C@H]([C@H]3[C@@H](NC2=O)Cc1ccccc1)C
• InChI: InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8-,16-15-/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
• InChIKey: GBOGMAARMMDZGR-WIPIJLBNSA-N

名称和登记号

名称

• IUPAC标准名: (5R,9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione
• IUPAC传统名: cytochalasin B
• 别名: 细胞松弛素 B 来源于Drechslera dematioidea; Phomin; Cytochalasin B from Drechslera dematioidea

登记号

• CAS号: 14930-96-2
• EC号: 239-000-2
• MDL号: MFCD00077704
• Beilstein号: 1096207
• PubChem SID: 24892890; 162228036
• PubChem CID: 24870911

理论计算性质

• Acid pKa: 13.110297
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 4.082357
• LogD (pH = 7.4): 4.082356
• Log P: 4.082357
• 摩尔折射率: 136.417 cm^3
• 极化性: 52.98627 Å^3
• 极化表面积: 95.86 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble10 mg/mL
• 外观: white powder

安全信息

• RTECS编号: RO0205000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 1544
• 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: 63-26/27/28
• 安全公开号: 28-36/37-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330-H361
• GHS警示性声明: P260-P264-P280-P284-P301 + P310-P302 + P350
• 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 1544 6.1/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 产品质量级别: PREMIUM

详细说明

Sigma Aldrich - C6762

Biochem/physiol Actions
One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin,1 and in studies on cytokinesis.2 Probe for the two hexose-transport systems in rat L6 myoblasts.3
Cell permeable fungal toxin that disrupts contractile microfilaments by inhibiting actin polymerization. This, in turn, induces DNA fragmentation, inhibits cell division, and disrupts many cell processes. Inhibits glucose transport.