C16-鞘氨醇 | 6982-09-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: C16-鞘氨醇
• 英文名称: hexadecasphingosine
• 英文别名: (E,2S,3R)-2-aminohexadec-4-ene-1,3-diol
• CAS: 6982-09-8
• 化学式: C₁₆H₃₃NO₂
• 分子量: 271.444
• InChiKey: BTUSGZZCQZACPT-YYZTVXDQSA-N

物化性质

• 沸点：
  419.6±45.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：10mg/mL； DMSO：2mg/mL；乙醇：可混溶

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C16-鞘氨醇 在 吡啶 、 sodium hydroxide 、 四溴化碳 作用下， 以 1,4-二氧六环 为溶剂， 生成 dimethyl (2S,3R,4E)-2-(tert-butoxycarbonylamino)-3-hydroxyoctadec-4-en-1-ylphosphate
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001
• 作为产物：
  描述：

  十二醛 在 盐酸 、 zinc(II) tetrahydroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 C16-鞘氨醇
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001

文献信息

• An efficient, stereoselective synthesis of 4-E- and 4-Z-d-erythro-sphingenine and related compounds from 2-amino-2-deoxy-d-glucose
  作者：Tamio Sugawara、Masayuki Narisada

  DOI：10.1016/0008-6215(89)85012-8

  日期：1989.12

  Efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenines having C16, C18, and C20 carbon-chains was achieved in 13 steps, starting from allyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. 2-Amino-1,6-di-O-tert- butyldiphenylsilyl-2-N,3-O-carbonyl-2-deoxy-D -allitol was used as the key intermediate.

  从烯丙基2-苄氧基羰基氨基-2-脱氧-α-D-吡喃葡萄糖苷开始，由13个步骤完成了具有C16，C18和C20碳链的4-E-和4-ZD-赤型-鞘氨醇的高效，立体选择性合成。使用2-氨基-1,6-二-O-叔丁基二苯基甲硅烷基-2-N，3-O-羰基-2-脱氧-D-烯丙醇作为关键中间体。
• New Cytotoxic Cerebrosides from the Red Sea Cucumber Holothuria spinifera Supported by In-Silico Studies
  作者：Reda F. A. Abdelhameed、Enas E. Eltamany、Dina M. Hal、Amany K. Ibrahim、Asmaa M. AboulMagd、Tarfah Al-Warhi、Khayrya A. Youssif、Adel M. Abd El-kader、Hashim A. Hassanean、Shaimaa Fayez、Gerhard Bringmann、Safwat A. Ahmed、Usama Ramadan Abdelmohsen

  DOI：10.3390/md18080405

  日期：——

  fractionation of a methanolic extract of the Red Sea cucumber Holothuria spinifera and LC-HRESIMS-assisted dereplication resulted in the isolation of four compounds, three new cerebrosides, spiniferosides A (1), B (2), and C (3), and cholesterol sulfate (4). The chemical structures of the isolated compounds were established on the basis of their 1D NMR and HRMS spectral data. Metabolic profiling of the H. spinifera

  生物活性指导的红海参Holholuria spinifera甲醇提取物的分馏和LC-HRESIMS辅助去复制导致了四种化合物，三种新的脑苷，Spiniferosides A（1），B（2）和C（3）的分离。和硫酸胆固醇（4）。分离出的化合物的化学结构是根据其1D NMR和HRMS光谱数据确定的。棘轮虫的代谢谱提取物表明存在多种次生代谢产物，主要是羟基脂肪酸，二萜，三萜和脑苷。测试分离的化合物对乳腺癌MCF-7细胞系的体外细胞毒性。化合物1，2，3，和4显示的有前途的细胞毒性活性对MCF-7细胞，用IC 50个的13.83值，8.13，8.27，和35.56微米，分别相比于标准药物多柔比星的（IC 50 8.64μM） 。另外，对于化合物进行对接研究1，2，3，和4阐明它们与SET蛋白活性位点的结合相互作用，SET蛋白是蛋白磷酸酶2A（PP2A）的抑制剂，这可以解释其细胞毒性活性。这项研究强
• METABOLOMIC REVISION OF MAMMALIAN INFANTS
  申请人：Evolve Biosystems Inc.

  公开号：EP3681521A1

  公开（公告）日：2020-07-22
• [EN] METABOLOMIC REVISION OF MAMMALIAN INFANTS<br/>[FR] RÉVISION MÉTABOLOMIQUE DE NOURRISSONS MAMMIFÈRES
  申请人：EVOLVE BIOSYSTEMS INC

  公开号：WO2019055718A1

  公开（公告）日：2019-03-21

  The inventions described herein relate generally to the use of compositions to increase output of particular metabolites in the gut of a nursing infant mammal including humans. These compositions generally comprise one or more bacterial strains selected for their growth on mammalian milk oligosaccharides, a source of mammalian milk oligosaccharides, and, optionally, nutritive components required for the growth of that infant mammal.
• Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors
  作者：Hyun-Suk Lim、Jeong-Ju Park、Kwangseok Ko、Mee-Hyun Lee、Sung-Kee Chung

  DOI：10.1016/j.bmcl.2004.03.001

  日期：2004.5

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.