1-Arachidonoyl-sn-glycerol | 124511-15-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-Arachidonoyl-sn-glycerol
• 英文别名: 1-arachidonoylglycerol；1-AG；(2S)-2,3-dihydroxypropyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate；[(2S)-2,3-dihydroxypropyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 124511-15-5
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: DCPCOKIYJYGMDN-HUDVFFLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Arachidonoyl-sn-glycerol 、 adenosine 5'-triphosphate 生成 1-Arachidonoyl-sn-glycerol 3-phosphate(2-) 、 adenosine 5'-diphosphate 、 氢(+1)阳离子
  参考文献：
  名称：

  MuLK, a Eukaryotic Multi-substrate Lipid Kinase

  摘要：

  We report the identification and characterization of a novel lipid kinase that phosphorylates multiple substrates. This enzyme, which we term MuLK for multisubstrate lipid kinase, does not belong to a previously described lipid kinase family. MuLK has orthologs in many organisms and is broadly expressed in human tissues. Although predicted to be a soluble protein, MuLK co-fractionates with membranes and localizes to an internal membrane compartment. Recombinant MuLK phosphorylates diacylglycerol, ceramide, and 1-acylglycerol but not sphingosine. Although its affinity for diacylglycerol and ceramide are similar, MuLK exhibits a higher V-max toward diacylglycerol in vitro, consistent with it acting primarily as a diacylglycerol kinase. MuLK activity was inhibited by sphingosine and enhanced by cardiolipin. It was stimulated by calcium when magnesium concentrations were low and inhibited by calcium when magnesium concentrations were high. The effects of charged lipids and cations on MuLK activity in vitro suggest that its activity in vivo is tightly regulated by cellular conditions.

  DOI：

  10.1074/jbc.m405932200
• 作为产物：
  描述：

  2-花生酰基甘油 在 大麻素 作用下， 以 乙腈 为溶剂， 生成 1-Arachidonoyl-sn-glycerol
  参考文献：
  名称：

  2-AG与其异构体1-AG的比率是CB1受体激活的固有精细调节机制。

  摘要：

  内源性大麻素是多效性脂质使者，通过激活大麻素受体强烈影响细胞内Ca2 +的浓度，从而在细胞生理学中发挥促稳态作用。最著名的内源性大麻素'2-AG'在水溶液中化学上不稳定，因此其分子重排导致1-AG的形成，可能会影响2-AG介导的信号传导，具体取决于其的相对浓度和效力。两个异构体。为了预测这种分子重排在生理过程和2-AG实验中是否可能相关，在这里我们研究了2-AG的异构化是否对2-AG诱导的CB1介导的Ca2 +信号转导有影响。我们发现有效2-AG浓度的异构化依赖性下降仅导致CB1转染的COS7细胞中Ca2 +信号转导减弱。我们还发现1-AG通过激活CB1诱导Ca2 +瞬变，但其工作浓度是2-AG的三倍。通过快速制备2-AG溶液来降低2-AG的浓度，同时防止1-AG的形成，会导致Ca2 +信号的显着减少。但是，两种异构体在固定总浓度下的各种混合物-模拟随时间的异构化过程-减弱了2-AG效力的下降，从而导致CB1介导的Ca2

  DOI：

  10.3389/fncel.2017.00039

文献信息

• FATTY ACID AMIDE HYDROLASE INHIBITORS
  申请人：Makriyannis Alexandros

  公开号：US20090306016A1

  公开（公告）日：2009-12-10

  Disclosed are compounds of formula R—X—Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CB1i and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.

  公开了一种R-X-Y式化合物，可用于抑制脂肪酸酰胺水解酶（FAAH）的作用。抑制脂肪酸酰胺水解酶（FAAH）将减缓FAAH水解作用引起的内源性大麻素配体的正常降解和失活，并允许更高水平的内源性大麻素配体保持存在。这些更高水平的内源性大麻素配体提供了对大麻素CB1i和CB2受体的增加刺激，并产生与大麻素受体激活相关的生理效应。它们还将增强其他外源性大麻素配体的效果，并允许它们在较低浓度下产生其效果，与不抑制脂肪酸酰胺水解酶（FAAH）作用的系统相比。因此，一种抑制脂肪酸酰胺水解酶（FAAH）对内源性大麻素配体失活的化合物可能会增加内源性大麻素的水平，从而增强大麻素受体的激活。因此，该化合物可能不直接调节大麻素受体，但通过增加内源性大麻素配体的水平间接刺激大麻素受体。它还可以增强其他外源性大麻素配体的效果和作用持续时间，这些配体被用于引发大麻素反应。
• Urea/carbamates FAAH MAGL or dual FAAH/MAGL inhibitors and uses thereof
  申请人：Northeastern University

  公开号：US10570146B2

  公开（公告）日：2020-02-25

  Disclosed are compounds that may be used to inhibit the action of fatty acid amide hydrolase (FAAH), monoacylglycerol lipase (MAGL) or dual FAAH/MAGL. More particularly, compounds of formula II have utility in a variety of therapeutic uses such as treatment of pain, inflammation, neuropathy, or appetite disorder.

  本发明公开了可用于抑制脂肪酸酰胺水解酶（FAAH）、单酰甘油脂肪酶（MAGL）或 FAAH/MAGL 双重作用的化合物。更具体地说，式 II 的化合物 具有多种治疗用途，如治疗疼痛、炎症、神经病变或食欲不振。
• Cannabinoid glycoside prodrugs and methods of synthesis
  申请人：Graphium Biosciences, Inc.

  公开号：US11207414B2

  公开（公告）日：2021-12-28

  The present invention relates to cannabinoid glycoside prodrugs suitable for site- and tissue-specific delivery of cannabinoid molecules. The present invention also relates to methods of forming the cannabinoid glycoside prodrugs through glycosyltransferase mediated glycosylation of cannabinoid molecules.

  本发明涉及适用于大麻素分子部位和组织特异性递送的大麻素苷原药。本发明还涉及通过糖基转移酶介导的大麻素分子糖基化形成大麻素苷原药的方法。
• Compositions and methods for modulating ABHD2 activity
  申请人：The Regents of the University of California

  公开号：US11273167B2

  公开（公告）日：2022-03-15

  The present disclosure provides compositions and methods of modulating abhydrolase domain-containing protein-2 (ABHD2). The present disclosure provides methods of identifying agents that modulate ABHD2 activity.

  本公开提供了调节含abhydrolase结构域蛋白-2（ABHD2）的组合物和方法。 本公开提供了鉴定调节 ABHD2 活性的制剂的方法。
• Congeners of acetaminophen and related compounds as substrates for fatty acid conjugation and their use in treatment of pain, fever and inflammation
  申请人：——

  公开号：US20040209959A1

  公开（公告）日：2004-10-21

  The present invention relates to new analgesic, antipyretic and/or anti-inflammatory compounds represented by the general formula X—Y, in which X is a benzyl group, a saturated or unsaturated cycloalkyl group (I,II) or a non-cyclic, straight or branched alkyl group (III,IV).

  本发明涉及通式 X-Y 所代表的新型镇痛、解热和/或消炎化合物，其中 X 是苄基、饱和或不饱和环烷基（I,II）或非环状、直链或支链烷基（III,IV）。