hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase编号: 154497
• 分子式: C21H46NO4P
• 平均质量: 407.568001
• 单一同位素质量: 407.31644559
• SMILES: CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C
• Canonical SMILES: CCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4/h5-21H2,1-4H3
• InChIKey: PQLXHQMOHUQAKB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC传统名: miltex
• 别名: Choline hexadecyl phosphate; HePC; Hexadecyl phosphocholine; Miltefosine; Miltefosine (Hexadecylphosphocholine); 2-[[(Hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium; Hexadecylphosphocholine; Hexadecylphosphorylcholine; Miltefosine; Miltex; n-Hexadecylphosphocholine; n-Hexadecylphosphorylcholine; Miltefosine

登记号

• CAS号: 58066-85-6
• MDL号: MFCD00133396
• PubChem SID: 162248636
• PubChem CID: 3599

理论计算性质

• Acid pKa: 1.8803148
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 4.2743464
• LogD (pH = 7.4): 4.2744484
• Log P: 2.2508485
• 摩尔折射率: 125.5131 cm^3
• 极化性: 45.86225 Å^3
• 极化表面积: 58.59 Å^2
• 可自由旋转的化学键: 20
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: soluble10 mg/mL, clear, colorless

安全信息

• RTECS编号: KH2890000
• 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): 3
• 危险公开号: 22-43
• 安全公开号: 36/37
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H334
• GHS警示性声明: P261-P301 + P310-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: room temp

药理学性质

• 作用靶点: Akt

产品相关信息

• 纯度: ≥98% (perchloric acid titration)
• 成盐信息: Free Base
• 简要说明: zwitterionic
• Empirical Formula (Hill Notation): C21H46NO4P

详细说明

Sigma Aldrich - M5571

Biochem/physiol Actions
Inhibitor of protein kinase C and of phosphatidylcholine synthesis. Used for the treatment of visceral and cutaneous leishmaniasis. Active against metronidazole-resistant and -susceptible strains of Trichomonas vaginalis1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M5571.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M344460

A phospholipid drug with antineoplastic and antiprotozoal/antifungal properties, also acts as an Akt inhibitor, and under investigation as a potential therapy against HIV infection.

参考文献

• Chugh, P., et al al.: Retrovirology, 5, 11 (2008)
• Dorio, T., et al.: Antimicrob. Agents Chemother., 52, 2855 (2008)