O-去甲基霉酚酸 | 31858-65-8

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: O-去甲基霉酚酸
• 中文别名: 霉酚酸二羟基类似物；霉酚酸O-去甲基杂质
• 英文名称: nor-O-methylmycophenolic acid
• 英文别名: O-desmethylmycophenolic acid；demethylmycophenolic acid；DMMPA；6-(4,6-Dihydroxy-7-methyl-3-oxo-phthalan-5-yl)-4-methyl-hex-4t-ensaeure；Nor-O-methylmycophenolsaeure；O-Desmethyl Mycophenolic Acid；(E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
• CAS: 31858-65-8
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: MHSRNZSBNXFMLF-FPYGCLRLSA-N

物化性质

• 熔点：
  137-140°C
• 沸点：
  635.5±55.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

ADMET

代谢

6-O-去甲基霉酚酸（DM-MPA）是霉酚酸已知的人体代谢物。

6-O-desmethyl-MPA (DM-MPA) is a known human metabolite of mycophenolic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  O-去甲基霉酚酸 在 吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 [7-(2-methoxyethoxymethoxy)-6-[(E)-6-methoxy-3-methyl-6-oxohex-2-enyl]-4-methyl-1-oxo-3H-2-benzofuran-5-yl] pyridine-3-carboxylate
  参考文献：
  名称：

  Mycophenolic acid as a latent agonist of PPARγ

  摘要：

  Mycophenolic acid (MPA), known as an inhibitor of inosine monophosphate dehydrogenase (IMPDH), was found to inhibit the differentiation of 3T3-L1 pre-adipocytes into mature adipocytes. Although the effect of MPA was attributed to inhibition of IMPDH, we uncovered a hidden biological property of MPA as an agonist of peroxisome proliferator activated receptor gamma (PPAR gamma). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.059
• 作为产物：
  描述：

  霉酚酸 在 lithium iodide 作用下， 以88.5%的产率得到O-去甲基霉酚酸
  参考文献：
  名称：

  参与霉酚酸生物合成的O-甲基转移酶MpaG'的功能表征

  摘要：

  青霉菌 基因组采矿：A基因支持群集MPA' -负责对霉酚酸（MPA）的生物合成已经从识别P.短密NRRL 864，和由编码的O-甲基MPAG'已经被表征。它不仅催化脱甲基麦考酚酸（DMMPA）的甲基化形成MPA，而且还使DMMPA的两种衍生物甲基化。

  DOI：

  10.1002/cbic.201402600

文献信息

• PROCESS FOR PREPARING MYCOPHENOLATE MOFETIL
  申请人：Choi Byoung Taek

  公开号：US20100298560A1

  公开（公告）日：2010-11-25

  The present invention relates to an improved method of manufacturing mycophenolate mofetil. More particularly, the present invention relates to a method of manufacturing mycophenolate mofetil with high purity comprising : a) converting mycophenolate to an amine salt by reacting with an amine base; and b) reacting the resultant with a halogenating agent and 2-morpholinoethanol continuously.
• Mycophenolic acid as a latent agonist of PPARγ
  作者：Makoto Ubukata、Hitomi Takamori、Misaki Ohashi、Shinya Mitsuhashi、Kaoru Yamashita、Tomohisa Asada、Noriyuki Nakajima、Nobuyasu Matsuura、Mie Tsuruga、Keiko Taki、Junji Magae

  DOI：10.1016/j.bmcl.2007.06.059

  日期：2007.9

  Mycophenolic acid (MPA), known as an inhibitor of inosine monophosphate dehydrogenase (IMPDH), was found to inhibit the differentiation of 3T3-L1 pre-adipocytes into mature adipocytes. Although the effect of MPA was attributed to inhibition of IMPDH, we uncovered a hidden biological property of MPA as an agonist of peroxisome proliferator activated receptor gamma (PPAR gamma). (c) 2007 Elsevier Ltd. All rights reserved.
• Functional Characterization of MpaG′, the O-Methyltransferase Involved in the Biosynthesis of Mycophenolic Acid
  作者：Wei Zhang、Shaona Cao、Li Qiu、Fengxia Qi、Zhong Li、Ying Yang、Shaohua Huang、Fali Bai、Changning Liu、Xiaobo Wan、Shengying Li

  DOI：10.1002/cbic.201402600

  日期：2015.3.2

  Penicillium­ genome mining: A gene cluster—mpa′—responsible for the biosynthesis of mycophenolic acid (MPA) has been identified from P. brevicompactum NRRL 864, and the O‐methyltransferase encoded by mpaG′ has been characterized. It not only catalyzed the methylation of demethylmycophenolic acid (DMMPA) to form MPA, but also methylated two derivatives of DMMPA.

  青霉菌 基因组采矿：A基因支持群集MPA' -负责对霉酚酸（MPA）的生物合成已经从识别P.短密NRRL 864，和由编码的O-甲基MPAG'已经被表征。它不仅催化脱甲基麦考酚酸（DMMPA）的甲基化形成MPA，而且还使DMMPA的两种衍生物甲基化。