N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]heptadecanamide

• ChemBase编号: 169878
• 分子式: C35H69NO3
• 平均质量: 551.92726
• 单一同位素质量: 551.52774507
• SMILES: OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(=O)CCCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C35H69NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-35(39)36-33(32-37)34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h28,30,33-34,37-38H,3-27,29,31-32H2,1-2H3,(H,36,39)/b30-28+/t33-,34+/m0/s1
• InChIKey: ICWGMOFDULMCFL-QKSCFGQVSA-N

名称和登记号

名称

• IUPAC标准名: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]heptadecanamide
• IUPAC传统名: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]heptadecanamide
• 别名: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]heptadecanamide; N-Heptadecanoyl-D-erythro-sphingosine

登记号

• CAS号: 67492-16-4
• PubChem SID: 162264010
• PubChem CID: 44584335

理论计算性质

• Acid pKa: 13.619749
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 11.309922
• LogD (pH = 7.4): 11.309923
• Log P: 11.309924
• 摩尔折射率: 170.3767 cm^3
• 极化性: 67.437706 Å^3
• 极化表面积: 69.56 Å^2
• 可自由旋转的化学键: 31
• 里宾斯基五规则: false

详细说明

Toronto Research Chemicals - H281225

Sphingosine derivative from red algae of the Ceramiales. Sphingolipids, such as ceramides and cerebrosides, are important molecules in the formation and maintenance of the epidermal barrier to water vapor diffusion.

参考文献

• Vadas, P., et al.: J. Lipid Mediator, 8, 1 (1993)
• Balboa, M., et al.: J. Biol. Chem., 271, 32381 (1993)
• Koumanov, K., et al.: Biochem. J., 363, 45 (1993)
• Tietge, U., et al.: J. Lipid Res., 46, 1604 (1993)