arachidonamide of γ-amino-n-butyric acid

• 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: arachidonamide of γ-amino-n-butyric acid
• 英文别名: N-arachidonoyl GABA；N-arachidonoyl-gama-butyric acid；N-arachidonoyl γ-aminobutyric acid；N-arachidonoyl-gamma-aminobutyric acid；N-arachidonyl 4-aminobutyric acid；Nagaba；4-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]butanoic acid
• 化学式: C₂₄H₃₉NO₃
• 分子量: 389.579
• InChiKey: JKUDIEXTAYKJNX-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 水 为溶剂， 反应 2.5h， 生成 arachidonamide of γ-amino-n-butyric acid
  参考文献：
  名称：

  Priller, Josef; Briley, Eileen M.; Mansouri, Jaleh, Molecular Pharmacology, 1995, vol. 48, # 2, p. 288 - 292

  摘要：

  DOI：

文献信息

• Arachidonoyl amino acids and arachidonoyl peptides: Synthesis and properties
  作者：V. V. Bezuglov、N. M. Gretskaya、A. V. Blazhenova、E. L. Andrianova、M. G. Akimov、M. Yu. Bobrov、I. V. Nazimov、M. A. Kisel’、O. L. Sharko、A. V. Novikov、N. V. Krasnov、V. P. Shevchenko、K. V. Shevchenko、T. V. V’yunova、N. F. Myasoedov

  DOI：10.1134/s1068162006030046

  日期：2006.5

  N-Arachidonoyl (AA) derivatives of amino acids (glycine, phenylalanine, proline, valine, gamma-amino butyric acid (GABA), dihydroxyphenylalanine, tyrosine, tryptophan, and alanine) and peptides (Semax, MEHFPGP, and PGP) were synthesized in order to study the biological properties of acylamino acids. The mass spectra of all the compounds at atmospheric pressure electrospray ionization display the most

  氨基酸（甘氨酸，苯丙氨酸，脯氨酸，缬氨酸，γ-氨基丁酸（GABA），二羟基苯丙氨酸，酪氨酸，色氨酸和丙氨酸）和肽（Semax，MEHFPGP和PGP）的N-花生四烯酸（AA）衍生物被合成。为了研究酰基氨基酸的生物学特性。大气压下电喷雾电离时所有化合物的质谱图显示质子化分子离子的最强峰。这些化合物的检出限为每个样品10 fmol。在所有研究的酰基氨基酸中，AA-Gly对大鼠脑中的脂肪酸酰胺水解酶表现出最高的抑制活性（IC50 6.5 microM）。AA-Phe，AA-Tyr和AA-GABA表现出微弱但可检测的抑制作用（分别为IC50 55、60和50 microM）。酰化氨基酸本身（AA-Gly除外）对这种酶的水解稳定。所有的花生四烯酸氨基酸都能不同程度地抑制白菜磷脂酶D。事实证明，AA-GABA和AA-Phe活性最高（分别为IC50 20和27 microM）。试图检测大鼠肝脏和神经组织
• 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。
• 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.
• METHODS FOR IDENTIFICATION, ASSESSMENT, PREVENTION, AND TREATMENT OF METABOLIC DISORDERS USING PM20D1 AND N-LIPIDATED AMINO ACIDS
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：EP3368157B1

  公开（公告）日：2022-06-29