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

• ChemBase编号: 90887
• 分子式: C26H51NO3
• 平均质量: 425.68804
• 单一同位素质量: 425.3868945
• SMILES: O=C(N[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)CO)CCCCCCC
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCCCC)CO)O
• InChI: InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1
• InChIKey: APDLCSPGWPLYEQ-WRBRXSDHSA-N

名称和登记号

名称

• IUPAC标准名: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide; N-[(2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
• IUPAC传统名: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide; N-[(2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
• 别名: C8 Ceramide; C8 ceramide; N-Octanoyl-D-sphingosine; N-Octanoylsphingosine; N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]octanamide; [R-[R*,S*-(E)]]-N-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]octanamide; D-erythro-N-Octanoylsphingosine; N-Octanoyl-C18-sphingosine; N-Octanoyl-D-erythro-sphingosine

登记号

• CAS号: 74713-59-0
• MDL号: MFCD00236496
• PubChem SID: 162077596; 24897955
• PubChem CID: 5702614

理论计算性质

• Acid pKa: 13.677088
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 7.3088045
• LogD (pH = 7.4): 7.3088055
• Log P: 7.308806
• 摩尔折射率: 128.9677 cm^3
• 极化性: 50.832943 Å^3
• 极化表面积: 69.56 Å^2
• 可自由旋转的化学键: 22
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Dichloromethane; DMSO or ethanol: soluble; Ethyl Acetate; Methanol
• 外观: Off White Solid; waxy solid
• 熔点: 68-70°C

安全信息

• 保存条件: -20°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 运输包装: wet ice
• Empirical Formula (Hill Notation): C26H51NO3

详细说明

Apollo Scientific Ltd - OR6270T

A biologically active, cell permeable, nonphysiologic ceramide analog. It induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase.

Sigma Aldrich - O1882

Biochem/physiol Actions
Synthetic anaolgue of natural ceramide, activates protein kinase C, stimulates IL-2 production and induces apoptosis.

Toronto Research Chemicals - C262700

A biologically active, cell permeable, but nonphysiologic ceramide analog. It induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase. It stimulates IL-2 secretion and induces apoptosis.

参考文献

• Mathias, S., et al.: Proc. Natl. Sci. USA, 88, 10009 (1991)
• Mathias, S., et al.: Science, 259, 519 (1991)
• Jarvis, W.D., et al.: Proc. Natl. Acad. Sci. USA, 91, 73 (1994)