sphingomyelin | 60322-02-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: sphingomyelin
• 英文别名: SM (d18:0/16:0)；N-Palmitoyl-D-erythro-dihydro-sphingosin-1-phosphorsaeure-cholinester；D-erythro-N-palmityl-dihydrosphingomyelin；N-Palmitoyldihydrosphingomyelin；[(2S,3R)-2-(hexadecanoylamino)-3-hydroxyoctadecyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 60322-02-3
• 化学式: C₃₉H₈₁N₂O₆P
• 分子量: 705.056
• InChiKey: QHZIGNLCLJPLCU-QPPIDDCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  48
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-棕榈酰-D-鞘磷脂 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 sphingomyelin
  参考文献：
  名称：

  METHOD OF ISOLATING SPHINGOLIPIDS FROM CORDYCEPS AND THEIR USE

  摘要：

  一种从冬虫夏草中分离至少一种鞘脂成分的方法，所选的鞘脂成分包括鞘氨醇基部分、鞘烷酸酰胺部分、糖鞘脂部分或磷鞘脂部分，特别是从野生型冬虫夏草中分离，可获得含有鞘氨醇基、鞘烷酸酰胺、糖鞘脂或磷鞘脂中一种成分增加的鞘脂成分。分离的鞘脂成分中含有迄今未报告过的显着鞘脂成分，并具有特殊的免疫抑制活性。一种治疗患有自身免疫疾病或过敏疾病等炎症性疾病的受试者的方法，包括给受试者投与从冬虫夏草中分离的鞘脂。一种治疗患有炎症性疾病的受试者的方法，包括给受试者投与某些鞘脂。此外，根据本发明，还提供了一种组合物，特别是一种包含至少一种鞘脂成分的药物组合物。

  公开号：

  US20170128507A1

文献信息

• METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS
  申请人：CERENIS THERAPEUTICS HOLDING SA

  公开号：US20160075634A1

  公开（公告）日：2016-03-17

  The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.

  本发明涉及合成鞘磷脂和二氢鞘磷脂的方法。本发明还涉及合成鞘氨醇和二氢鞘氨醇的方法。本发明还涉及合成鞘醇和二氢鞘醇的方法。
• <b>Studies on Sphingolipids. VII. Synthesis and Configuration of Natural Sphingomyelins</b>
  作者：David. Shapiro、H. M. Flowers

  DOI：10.1021/ja00865a036

  日期：1962.3
• Sphingomyelin synthase SMS2 displays dual activity as ceramide phosphoethanolamine synthase
  作者：Philipp Ternes、Jos F.H.M. Brouwers、Joep van den Dikkenberg、Joost C.M. Holthuis

  DOI：10.1194/jlr.m900230-jlr200

  日期：2009.11

  Sphingolipids are vital components of eukaryotic membranes involved in the regulation of cell growth, death, intracellular trafficking, and the barrier function of the plasma membrane (PM). While sphingomyelin (SM) is the major sphingolipid in mammals, previous studies indicate that mammalian cells also produce the SM analog ceramide phosphoethanolamine (CPE). Little is known about the biological role of CPE or the enzyme(s) responsible for CPE biosynthesis. SM production is mediated by the SM synthases SMS1 in the Golgi and SMS2 at the PM, while a closely related enzyme, SMSr, has an unknown biochemical function. We now demonstrate that SMS family members display striking differences in substrate specificity, with SMS1 and SMSr being monofunctional enzymes with SM and CPE synthase activity, respectively, and SMS2 acting as a bifunctional enzyme with both SM and CPE synthase activity. In agreement with the PM residency of SMS2, we show that both SM and CPE synthase activities are enhanced at the surface of SMS2-overexpressing HeLa cells. Our findings reveal an unexpected diversity in substrate specificity among SMS family members that should enable the design of specific inhibitors to target the biological role of each enzyme individually.-Ternes, P., J. F. H. M. Brouwers, J. van den Dikkenberg, and J. C. M. Holthuis. Sphingomyelin synthase SMS2 displays dual activity as ceramide phosphoethanolamine synthase. J. Lipid Res. 2009. 50: 2270-2277.
• [EN] LIPOSOMAL FORMULATIONS COMPRISING DIHYDROSPHINGOMYELIN AND METHODS OF USE THEREOF<br/>[FR] FORMULATIONS LIPOSOMALES RENFERMANT DE LA DIHYDROSPHINGOMYELINE, ET PROCEDES D'UTILISATION CORRESPONDANTS
  申请人：INEX PHARMACEUTICALS CORP

  公开号：WO2005120461A3

  公开（公告）日：2006-03-16
• US20140275590A1
  申请人：——

  公开号：US20140275590A1

  公开（公告）日：2014-09-18