(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate

• ChemBase编号: 132263
• 分子式: C34H50O12
• 平均质量: 650.7536
• 单一同位素质量: 650.33022704
• SMILES: CCCCCCCC(=O)O[C@H]1[C@H]2C(=C([C@@H]1OC(=O)/C(=C\C)/C)C)[C@H]1[C@]([C@H](C[C@]2(C)OC(=O)C)OC(=O)CCC)([C@](C(=O)O1)(C)O)O
• Canonical SMILES: CCCCCCCC(=O)O[C@@H]1[C@@H](OC(=O)/C(=C\C)/C)C(=C2[C@H]1[C@@](C)(OC(=O)C)C[C@@H]([C@]1([C@H]2OC(=O)[C@@]1(C)O)O)OC(=O)CCC)C
• InChI: InChI=1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1
• InChIKey: IXFPJGBNCFXKPI-FSIHEZPISA-N

名称和登记号

名称

• IUPAC标准名: (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate
• IUPAC传统名: thapsigargin
• 别名: Thapsigargin; Octanoic Acid (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b- decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[[(2Z)-2-methyl-1-oxo-2-butenyl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl Ester; (-)-Thapsigargin; Octanoic Acid [3S-[3α,3aβ,4α,6β,6aβ,7β,8α(Z),9bα]]-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl Ester; Thapsigargin

登记号

• CAS号: 67526-95-8
• MDL号: MFCD00083511
• PubChem SID: 24278762; 162226540
• PubChem CID: 446378

理论计算性质

• Acid pKa: 11.135566
• 质子受体: 7
• 质子供体: 2
• LogD (pH = 5.5): 4.3845243
• LogD (pH = 7.4): 4.3844457
• Log P: 4.3845253
• 摩尔折射率: 163.8158 cm^3
• 极化性: 65.89336 Å^3
• 极化表面积: 171.96 Å^2
• 可自由旋转的化学键: 17
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; DMSO: soluble; ethanol: soluble
• 外观: Off-White Solid; solid film
• 熔点: 84-90°C

安全信息

• 保存条件: -20°C Freezer
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 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: 36/37/38-42
• 安全公开号: 26-36/37/39
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H319-H334-H335
• GHS警示性声明: P261-P305 + P351 + P338-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 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 - T9033

Biochem/physiol Actions
Potent, cell-permeable, IP3-independent intracellular calcium releaser. Blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. Induces apoptosis by disrupting intracellular free Ca2+ levels; incorporated into chemotherapeutic prodrug formulations.

Sigma Aldrich - T124

Biochem/physiol Actions
Potent, cell-permeable, IP3-independent intracellular calcium releaser. Blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. Induces apoptosis by disrupting intracellular free Ca2+ levels; incorporated into chemotherapeutic prodrug formulations.

Toronto Research Chemicals - T339250

A widely used inhibitor of the ubiquitous sarco-endoplasmic reticulum Ca(2+)-ATPases in mammalian cells. It acts as a potent, cell-permeable, IP3-independent intracellular calcium releaser that blocks the transient increase in intracellular Ca2+ induced b

参考文献

• Treiman, M. et al.: Trends Pharmacol. Sci., 19, 131 (1998)
• Korge, P. et al.: Eur. J. Biochem., 265, 273 (1998)
• Tsukamoto, A. Cell Biol. Int., 17, 969 (1998)
• Kutinova C.N. et al.: Cell Biol. Toxicol., 23, 337 (1998)