{[(4E)-3-hydroxy-2-octanamidooctadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase编号: 163990
• 分子式: C26H52NO6P
• 平均质量: 505.667941
• 单一同位素质量: 505.35322502
• SMILES: CCCCCCCCCCCCC/C=C/C(C(COP(=O)(O)O)NC(=O)CCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/C(C(NC(=O)CCCCCCC)COP(=O)(O)O)O
• InChI: InChI=1S/C26H52NO6P/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(28)24(23-33-34(30,31)32)27-26(29)22-20-17-8-6-4-2/h19,21,24-25,28H,3-18,20,22-23H2,1-2H3,(H,27,29)(H2,30,31,32)/b21-19+
• InChIKey: VSSNYUXSRXINIP-XUTLUUPISA-N

名称和登记号

名称

• IUPAC标准名: {[(4E)-3-hydroxy-2-octanamidooctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC传统名: [(4E)-3-hydroxy-2-octanamidooctadec-4-en-1-yl]oxyphosphonic acid
• 别名: N-[2-Hydroxy-1-[(phosphonooxy)methyl]-3-heptadecen-1-yl]octanamide; N-Octanoylsphingosine-1-phosphate; C8 Ceramide-1-phosphate

登记号

• CAS号: 887353-95-9
• PubChem SID: 162258125
• PubChem CID: 6384103

理论计算性质

• Acid pKa: 1.528374
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): 4.781171
• LogD (pH = 7.4): 3.902242
• Log P: 7.0234156
• 摩尔折射率: 139.8406 cm^3
• 极化性: 55.07053 Å^3
• 极化表面积: 116.09 Å^2
• 可自由旋转的化学键: 24
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Dichloromethane; Methanol
• 外观: White Crystalline Solid
• 熔点: 138-140°C

详细说明

Toronto Research Chemicals - C262720

Stimulates DNA synthesis when added exogenously to cultured fibroblasts at 5μM. Mitogenic activity is antagonized by cell permeable ceramides.

参考文献

• Gomez-Munoz, A., et al.: Mol. Pharmacol., 47, 883 (1995)