N-arachidonoyl serine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-arachidonoyl serine
• 英文别名: N-Arachidonoyl-L-serine；N-ARAS；(2S)-3-hydroxy-2-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]propanoic acid
• 化学式: C₂₃H₃₇NO₄
• 分子量: 391.551
• InChiKey: FQUVPTVNRMUOPO-UPQKDGGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 碳酸氢钠 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 N-arachidonoyl serine
  参考文献：
  名称：

  Anandamide型化合物与脑大麻素受体结合的结构要求。

  摘要：

  为了建立与脑大麻素受体（CB1）结合的结构要求，我们合成了许多脂肪酸酰胺，乙醇酰胺和一些相关的简单衍生物，并确定了它们的Ki值。还检查了一些α-甲基或α，α-二甲基花生四烯酰基烷基酰胺。在20：4，n-6系列中，未取代的酰胺是惰性的；N-单烷基化，至少直至分支的戊基，导致显着的结合。N，N-二烷基化，在一个烷基上具有或不具有羟基化，导致活性的消除。在ω碳原子上的N-单烷基的羟基化保持活性。在20x，n-6序列中，x必须为3或4；否则，x为3。只有两个双键的存在会导致失活。在n-3系列中 报告的有限数据表明，衍生的乙醇酰胺比n-6系列中的同类化合物无活性或活性较低。对于邻氨基苯甲酰胺（化合物48、49），与羰基相邻的α碳的烷基化或二烷基化保持结合水平。但是，N-丙基衍生物（50-53）的α-单甲基化或α，α-二甲基化可增强结合并导致本研究中活性最高的化合物（Ki值为6.9 +/- 0.7至8

  DOI：

  10.1021/jm960752x

文献信息

• FATTY ACID AMIDES AND USES THEREOF
  申请人：Mechoulam Raphael

  公开号：US20110046222A1

  公开（公告）日：2011-02-24

  Provided are fatty acid amides of amino acids, uses thereof and pharmaceutical compositions including them.

  提供了氨基酸脂肪酰胺，以及其用途和包含它们的药物组成物。
• Ligand for G-protein coupled receptor GPR72 and uses thereof
  申请人：Euroscreen S.A.

  公开号：EP1867994A2

  公开（公告）日：2007-12-19

  The present invention relates to methods, reagents and kits for detecting of GPR72 polypeptide activity in a sample and identifying agents which modulate polypeptide activity. It further relates to antibodies raised against GPR72. It further relates to substances for preventing, treating and/or alleviating diseases or disorders characterized by dysregulation of GPR72 polypeptide signalling.

  本发明涉及检测样品中 GPR72 多肽活性和鉴定调节多肽活性的制剂的方法、试剂和试剂盒。本发明还涉及针对 GPR72 的抗体。本发明还涉及用于预防、治疗和/或缓解以 GPR72 多肽信号失调为特征的疾病或紊乱的物质。
• Pharmaceutical emulsion composition and use thereof
  申请人：College of Pharmacy of Taif University

  公开号：EP2653156A1

  公开（公告）日：2013-10-23

  The present invention relates to a pharmaceutical emulsion composition comprising: at least one drug, at least one amino acid, at least one fatty acid and at least one surfactant, wherein the amino acid, the fatty acid and the surfactant form micelles and the drug is encapsulated into the micelles and its use as a medicament, in particular for oral administration in treatment of hyperglycemia and diabetes.

  本发明涉及一种药用乳液组合物，该组合物包含：至少一种药物、至少一种氨基酸、至少一种脂肪酸和至少一种表面活性剂，其中氨基酸、脂肪酸和表面活性剂形成胶束，药物被包裹在胶束中，并用作药物，特别是用于口服治疗高血糖和糖尿病。
• Priller, Josef; Briley, Eileen M.; Mansouri, Jaleh, Molecular Pharmacology, 1995, vol. 48, # 2, p. 288 - 292
  作者：Priller, Josef、Briley, Eileen M.、Mansouri, Jaleh、Devane, William A.、Mackie, Ken、Felder, Christian C.

  DOI：——

  日期：——
• Identification of endogenous acyl amino acids based on a targeted lipidomics approach
  作者：Bo Tan、David K. O’Dell、Y. William Yu、M. Francesca Monn、H. Velocity Hughes、Sumner Burstein、J. Michael Walker

  DOI：10.1194/jlr.m900198-jlr200

  日期：2010.1

  Using a partially purified bovine brain extract, our lab identified three novel endogenous acyl amino acids in mammalian tissues. The presence of numerous amino acids in the body and their ability to form amides with several saturated and unsaturated fatty acids indicated the potential existence of a large number of heretofore unidentified acyl amino acids. Reports of several additional acyl amino acids that activate G-protein coupled receptors (e.g., N-arachidonoyl glycine, N-arachidonoyl serine) and transient receptor potential channels (e.g., N-arachidonoyl dopamine, N-acyl taurines) suggested that some or many novel acyl amino acids could serve as signaling molecules. Here, we used a targeted lipidomics approach including specific enrichment steps, nano-LC/MS/MS, high-throughput screening of the datasets with a potent search algorithm based on fragment ion analysis, and quantification using the multiple reaction monitoring mode in Analyst software to measure the biological levels of acyl amino acids in rat brain. We successfully identified 50 novel endogenous acyl amino acids present at 0.2 to 69 pmol g(-1) wet rat brain.-Tan, B., D. K. O'Dell, Y. W. Yu, M. F. Monn, H. V. Hughes, S. Burstein, and J. M. Walker. Identification of endogenous acyl amino acids based on a targeted lipidomics approach. J. Lipid Res. 2010. 51: 112-119.