(R)-3-(4-hydroxyphenyl)-2-palmitamidopropanoic 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: (R)-3-(4-hydroxyphenyl)-2-palmitamidopropanoic acid
• 英文别名: N-palmitoyl-D-tyrosine；(2R)-2-(hexadecanoylamino)-3-(4-hydroxyphenyl)propanoic acid
• 化学式: C₂₅H₄₁NO₄
• 分子量: 419.605
• InChiKey: IPAZGTSTZYXZAT-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  在 sodium hydroxide 作用下， 生成 (R)-3-(4-hydroxyphenyl)-2-palmitamidopropanoic acid
  参考文献：
  名称：

  Evaluation of Inhibitory Actions of Flavonols and Related Substances on Lysophospholipase D Activity of Serum Autotaxin by a Convenient Assay Using a Chromogenic Substrate

  摘要：

  Overproduction of lysophosphatidic acid (LPA) by lysophospholipase D/autotaxin (lysoPLD/ATX) is postulated to be involved in the promotion of cancer and atherosclerosis. A lysoPLD inhibitor may be utilized to ameliorate the LPA-related pathological conditions. In this study, a new assay was devised to quantify p-nitrophenol from hydrolysis of chromogenic substrate by serum lysoPLD without tedious lipid extraction procedures. Flavonols, phenolic acids, free fatty acids, and N-acyltyrosines inhibited lysoPLD activity in a micromolar range. They were classified into competitive, noncompetitive, or mixed type inhibitors. The results show that the low hydrophobicity of an inhibitor is a critical factor in its preference for the binding to a noncatalytic binding site over a catalytic binding site. Considering its reported bioavailability and the low dependency of its inhibitory activity on serum dilution, flavonol is likely to be a more effective lysoPLD inhibitor in human blood circulation in vivo than the other inhibitors including LPA.

  DOI：

  10.1021/jf904155a

文献信息

• [EN] N-ACYL-TYROSINE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE N-ACYLE-TYROSINE ET LEURS UTILISATIONS
  申请人：UNIV OF PRINCE EDWARD ISLAND

  公开号：WO2021046651A1

  公开（公告）日：2021-03-18

  Provided herein are compounds of Formula A, methods for the preparation thereof, and uses thereof for treating or preventing bacterial infections.

  本文提供了A式化合物，其制备方法以及用于治疗或预防细菌感染的用途。
• PHOSPHONATE DERIVATIVES AS AUTOTAXIN INHIBITORS
  申请人：Lynch Kevin R.

  公开号：US20100016258A1

  公开（公告）日：2010-01-21

  The present invention provides β-hydroxy phosphonate compounds that are autotaxin inhibitors.

  本发明提供了一种β-羟基膦酸酯化合物，它们是自动税感受器抑制剂。
• Phosphonate derivatives as autotaxin inhibitors
  申请人：Lynch Kevin R.

  公开号：US08378100B2

  公开（公告）日：2013-02-19

  The present invention provides β-hydroxy phosphonate compounds that are autotaxin inhibitors.

  本发明提供了一种自体税脂酰酰胺酶抑制剂β-羟基膦酸酯化合物。
• Shinitzky, Meir; Haimovitz, Rachel, Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12545 - 12549
  作者：Shinitzky, Meir、Haimovitz, Rachel

  DOI：——

  日期：——
• US8378100B2
  申请人：——

  公开号：US8378100B2

  公开（公告）日：2013-02-19