(1S,2R,8R)-octahydroindolizine-1,2,8-triol

• ChemBase编号: 131045
• 分子式: C8H15NO3
• 平均质量: 173.2096
• 单一同位素质量: 173.10519335
• SMILES: C1C[C@H](C2[C@@H]([C@@H](CN2C1)O)O)O
• Canonical SMILES: O[C@@H]1CN2C([C@@H]1O)[C@H](O)CCC2
• InChI: InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7?,8-/m1/s1
• InChIKey: FXUAIOOAOAVCGD-DCDLSZRSSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,8R)-octahydroindolizine-1,2,8-triol
• IUPAC传统名: (1S,2R,8R)-octahydroindolizine-1,2,8-triol
• 别名: (1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol; Swainsonine

登记号

• CAS号: 72741-87-8
• MDL号: MFCD00017554
• Beilstein号: 4175740
• PubChem SID: 162225323; 24899832; 24899779
• PubChem CID: 16219982

理论计算性质

• Acid pKa: 13.284674
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -4.78174
• LogD (pH = 7.4): -3.4669168
• Log P: -1.4067957
• 摩尔折射率: 43.1178 cm^3
• 极化性: 17.444298 Å^3
• 极化表面积: 63.93 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: lyophilized powder

安全信息

• RTECS编号: NM2408666
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: ≥98% (TLC)
• 生物来源: from locoweed; from Metarrhizium anisopliae; from Rhizoctonia leguminicola; from synthetic
• Empirical Formula (Hill Notation): C8H15NO3

详细说明

Sigma Aldrich - S6640

Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.1 It inhibits glycoprotein processing2 and also acts as immune modulator.1,3

Sigma Aldrich - S8195

Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.3 It inhibits glycoprotein processing4 and also acts as immune modulator.3,5
Swainsonine is an indolizidine alkaloid from the plant Metarrhizium anisopliae that is used as a potent α-mannosidase inhibitor1. Product S8195 has been used in chemical inhibition assays of CHO Lec2 cells to inhibit glycosylation 2.
Biochem/physiol Actions
Swainsonine is a potent α-mannosidase inhibitor. It also has antimetastatic, antiproliferative, and immunomodulatory activity 1. It also inhibits glycoprotein processing.
Physical properties
Soluble in water, methanol, DMSO

Sigma Aldrich - S9263

Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.1 It inhibits glycoprotein processing2 and also acts as immune modulator.1,3

Sigma Aldrich - 86204

Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.1 It inhibits glycoprotein processing2 and also acts as immune modulator.1,3
Other Notes
Inhibitor of Golgi mannosidase II and hence glycoprotein biosynthesis4,5