methyl 3β-hydroxy-7,12-dioxo-5β-cholanate | 81847-12-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl 3β-hydroxy-7,12-dioxo-5β-cholanate
• 英文别名: 3β-hydroxy-7,12-dioxo-5β-cholanoic acid-(24)-methyl ester；3β-Hydroxy-7,12-dioxo-5β-cholansaeure-(24)-methylester；methyl (4R)-4-[(3S,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7,12-dioxo-2,3,4,5,6,8,9,11,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 81847-12-3
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: PMCNWQOSYVVSNW-SQBICPLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3β-hydroxy-7,12-dioxo-5β-cholanate 在 硼烷 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以0.75 g的产率得到methyl 3β,7α,12β-trihydroxy-5β-cholanate
  参考文献：
  名称：

  Potential bile acid metabolites. 7. 3,7,12-Trihydroxy-5.beta.-cholanic acids and related compounds

  摘要：

  DOI：

  10.1021/jo00136a031
• 作为产物：
  描述：

  sodium dehydrocholate 在 malt extract 、 甲烷磺酸 、 葡萄糖 、 Collybia velutipes 、 sodium sulfate 作用下， 以 水 为溶剂， 反应 168.03h， 生成 methyl 3β-hydroxy-7,12-dioxo-5β-cholanate
  参考文献：
  名称：

  脱氢胆酸的区域和立体选择性还原

  摘要：

  脱氢胆酸 (DHCA) 是一种非天然胆汁酸，由胆酸氧化制成。据报道，它通过两种担子菌（Trametes hirsuta 和 Collybia velutipes）进行生物转化。这些菌丝体对底物和攻击选择性表现出不同的亲和力：T. hirsuta 特别是区域选择性和立体选择性还原 3-keto 基团以产生 3 alpha-hydroxy-7,12-diketo-5 beta-cholan-24-oic acid (7,12-diketolithocolic acid) 为主要产品。对 DHCA 进行了许多不同的化学还原；其中，在高强度超声下与雷尼镍在水中的氢化证明具有高度的区域和立体选择性，仅产生 7,12-二酮基乙醇酸。由于一系列 1D 和 2D NMR 运行，包括 DEPT、NOESY、HH COSY、gHSQC 和 gHMBC，详细指定了 (1)H 和 (13)C 共振。

  DOI：

  10.1016/j.steroids.2006.01.004

文献信息

• Kyogoku, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1937, vol. 250, p. 253,255
  作者：Kyogoku

  DOI：——

  日期：——
• Yamasaki; Kyogoku, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1935, vol. 235, p. 43,45
  作者：Yamasaki、Kyogoku

  DOI：——

  日期：——
• Cloning, tissue expression pattern characterization and chromosome localization of human peptide methionine sulfoxide reductase cDNA
  作者：Peirong Hu、Long Yu、Min Zhang、Lihua Zheng、Fei Lan、Qiang Fu、Shouyuan Zhao

  DOI：10.1007/bf02886363

  日期：2000.12

  Oxidation and reduction of some amino acids are one of the molecular mechanisms for regulating the function of proteins. The oxidation of methionine (Met) to methionine sulfoxide (Met(O)) results in decreasing or loss of the biological activity of related proteins. It was found that peptide methionine sulfoxide reductase (msrA) can reduce Met(O) to Met and therefore restored the biological function of the oxidized proteins. To reveal the methionine oxidation-reduction mechanism in human body, in this study the cDNA sequence of bovine msrA was used as an information-probe to screen the human EST database. Based on a contig assembled from homologous ESTs, a 1 256-bp human MSRA cDNA was cloned from several human cDNA libraries. The cDNA contains an open reading frame (ORF) of 705 bp in length, which encodes 235 amino acid residues. Homology comparison revealed that human MSRA shares 88% and 61% identities with bovine and Escherichia coli msrA protein respectively. Expression pattern analysis revealed a single 1.6-kb transcript of human MSRA in most human tissues and with highest expression in kidney. By radiation hybrid panel mapping, the gene was localized to human chromosome 8p22-23 between markers D8S518 and D8S550. There are 2 human inherited diseases Keratolytic Winter Erythema and Microcephaly related genes in this region, it is inferred that human MSRA might be the candidate of the two diseases.