3,7-二羟基-3',4',5'-三甲氧基黄酮 | 132594-09-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3,7-二羟基-3',4',5'-三甲氧基黄酮
• 英文名称: 3',4',5'-O-trimethylrobinetin
• 英文别名: Robinetin trimethyl ether；3,7-dihydroxy-3',4',5'-trimethoxyflavone；3,7-DH-3',4',5'-TMOF；3,7-dihydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one；3,7-Dihydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-on；3,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• CAS: 132594-09-3
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: NJNGYVOYOVPWBB-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211°C
• 溶解度：
  可溶于DMSO（轻微超声处理）、甲醇（轻微超声处理）
• LogP：
  2.710 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

ADMET

代谢

3,7-二羟基-3'，4'，5'-三甲氧基黄酮已知的人类代谢物包括(2S,3S,4S,5R)-3,4,5-三羟基-6-[7-羟基-4-氧代-2-(3,4,5-三甲氧基苯基)色酮-3-基]氧杂环己烷-2-羧酸和(2S,3S,4S,5R)-3,4,5-三羟基-6-[3-羟基-4-氧代-2-(3,4,5-三甲氧基苯基)色酮-7-基]氧杂环己烷-2-羧酸。

3,7-Dihydroxy-3p,4p,5p-trimethoxyflavone has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[7-hydroxy-4-oxo-2-(3,4,5-trimethoxyphenyl)chromen-3-yl]oxyoxane-2-carboxylic acid and (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[3-hydroxy-4-oxo-2-(3,4,5-trimethoxyphenyl)chromen-7-yl]oxyoxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  3,7-二羟基-3',4',5'-三甲氧基黄酮 在 氢碘酸 、 乙酸酐 作用下， 生成 洋槐黄素
  参考文献：
  名称：

  Bellino; Venturella, Annali di Chimica, 1958, vol. 48, p. 111,118

  摘要：

  DOI：
• 作为产物：
  描述：

  3-hydroxy-7-methoxymethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 在 硫酸 、 溶剂黄146 作用下， 生成 3,7-二羟基-3',4',5'-三甲氧基黄酮
  参考文献：
  名称：

  Bellino; Venturella, Annali di Chimica, 1958, vol. 48, p. 111,118

  摘要：

  DOI：

文献信息

• 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。
• Tire with rubber containing flavone
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP1391327A1

  公开（公告）日：2004-02-25

  The invention relates to a rubber composition and a pneumatic tire having a component comprising a rubber containing the reaction product of a flavone and a methylene donor.

  本发明涉及一种橡胶组合物和充气轮胎，其成分包括含有黄酮和亚甲基供体反应产物的橡胶。
• Rubber composition and tire with rubber containing flavone
  申请人：The Goodyear Tire & Rubber Company

  公开号：EP2730431A1

  公开（公告）日：2014-05-14

  A rubber composition comprising a diene based elastomer and an adhesion promoter derived from a flavone, a methylene donor and a methylene acceptor is disclosed. The rubber composition is essentially free of cobalt. Also, a pneumatic tire comprising such a rubber composition is disclosed.

  本发明公开了一种橡胶组合物，该组合物包含一种二烯基弹性体和一种由黄酮、亚甲基供体和亚甲基受体衍生的附着力促进剂。该橡胶组合物基本上不含钴。此外，还公开了一种包含这种橡胶组合物的充气轮胎。
• COMPOSITIONS COMPRISING BLOCKERS OF L-DOPA RENAL CELL TRANSFER FOR THE TREATMENT OF PARKINSON'S DISEASE
  申请人：Portela & Ca., S.A.

  公开号：EP1267853B1

  公开（公告）日：2004-09-08
• Compositions comprising blockers of l-dopa renal cell transfer for the treatment of parkinson's disease
  申请人：——

  公开号：US20040242503A1

  公开（公告）日：2004-12-02

  A pharmaceutical composition for the treatment of Parkinson's disease comprises L -DOPA and at least one compound capable of blocking the L -DOPA renal cell outward transfer pathway; said blocking compound being chose from (a) a flavonoid phenyl benzopyran derivative; (b) a trans-stilbene derivative; or (c) phloretin [3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone]. The composition may also comprise an inhibitor of the enzyme amino acid decarboxylase (AADC), such a carbidopa or benserazide, and/or an inhibitor of the enzyme catechol- O -methyl transferase (COMT), such as entacapone or tolcapone. The composition is preferably administered in soli form and the L -DOPA may be administered simultaneously or sequentially with the L -DOPA renal cell outward transfer blocking compound.