diosmetin-7-O-glucuronide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: diosmetin-7-O-glucuronide
• 英文别名: (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid
• 化学式: C₂₂H₂₀O₁₂
• 分子量: 476.394
• InChiKey: XCKMDTYMOHXUHG-QAKXDBDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

ADMET

代谢

(2S,3S,4S,5R)-3,4,5-三羟基-6-[5-羟基-2-(3-羟基-4-甲氧基苯基)-4-氧代色酮-7-基]氧杂环己烷-2-羧酸是柚皮素的已知人体代谢物。

(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid is a known human metabolite of Diosmetin.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  香叶木素 、 UDP-glucuronic acid 在 human UDP-glucuronosyltransferase 1A₉ 、 magnesium chloride 、 alamethicin 、 糖质酸-1,4-内酯 作用下， 生成 diosmetin-7-O-glucuronide
  参考文献：
  名称：

  Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches

  摘要：

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。

  DOI：

  10.1007/s11095-012-0666-z

文献信息

• Compositions comprising small molecular inhibitors suitable to inhibit and stimulate signaling pathways in a manner leading to prevention of muscle atrophy
  申请人：Biosens Croatia

  公开号：EP3132692A1

  公开（公告）日：2017-02-22

  The present invention relates to the field of prevention and treatment of muscle atrophy. More particular, the present invention relates to a composition comprising hesperetin, (-) epicatechin and myricetin. The present invention further relates to the use of said composition as inhibitor and stimulator for signaling pathways.

  本发明涉及肌肉萎缩的预防和治疗领域。更具体地说，本发明涉及一种由橙皮素、（-）表儿茶素和杨梅素组成的组合物。本发明进一步涉及所述组合物作为信号通路抑制剂和刺激剂的用途。
• USE OF A COMBINATION OF HESPERIDIN AND OF A MICROORGANISM FOR INFLUENCING THE BARRIER FUNCTION OF THE SKIN
  申请人：GUENICHE Audrey

  公开号：US20090068161A1

  公开（公告）日：2009-03-12

  The cosmetic use of at least an effective amount of hesperidin or of one of its derivatives in combination with at least an effective amount of at least one microorganism, in particular probiotic microorganism, or one of its fractions as agent for preventing a reduction in and/or for reinforcing the barrier function of the skin.
• [EN] USE OF A COMBINATION OF HESPERIDIN AND OF A MICROORGANISM FOR INFLUENCING THE BARRIER FUNCTION OF THE SKIN<br/>[FR] UTILISATION D'UNE COMBINAISON D'HESPÉRIDINE ET D'UN MICRO-ORGANISME POUR INFLUER SUR LA FONCTION DE BARRIÈRE DE LA PEAU
  申请人：OREAL

  公开号：WO2009031106A2

  公开（公告）日：2009-03-12

  The present invention relates to the cosmetic use of at least an effective amount of hesperidin or of one of its derivatives in combination with at least an effective amount of at least one microorganism, in particular probiotic microorganism, or one of its fractions as agent for preventing a reduction in and/or for reinforcing the barrier function of the skin.
• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。