7-hydroxy-3-(sulfooxy)-(3α,5β,7β)-cholan-24-oic acid | 68780-73-4

• 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: 7-hydroxy-3-(sulfooxy)-(3α,5β,7β)-cholan-24-oic acid
• 英文别名: 3-(sulfooxy)ursodeoxycholic acid；ursodeoxycholic acid 3-sulfate；3-sulfoursodeoxycholic acid；ursodeoxycholic acid 3-O-sulfate；UDCA-3S；(3a,5b,7b)-7-hydroxy-3-(sulfooxy)-Cholan-24-oic acid；(4R)-4-[(3R,5R,7S,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-sulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 68780-73-4
• 化学式: C₂₄H₄₀O₇S
• 分子量: 472.643
• InChiKey: WHMOBEGYTDWMIG-UZVSRGJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3-(sulfooxy)-(3α,5β,7β)-cholan-24-oic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三甲胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 S-(3-O-sulfo-ursodeoxycholyl)glutathione
  参考文献：
  名称：

  Synthesis of the 3-sulfates of S-acyl glutathione conjugated bile acids and their biotransformation by a rat liver cytosolic fraction

  摘要：

  The 3-sulfates of the S-acyl glutathione (GSH) conjugates of five natural bile acids (cholic, chenodeoxycholic, deoxycholic, ursodeoxycholic, and lithocholic) were synthesized as reference standards in order to investigate their possible formation by a rat liver cytosolic fraction. Their structures were confirmed by proton nuclear magnetic resonance, as well as by means of electrospray ionization-linear ion-trap mass spectrometry with negative-ion detection. Upon collision-induced dissociation, structurally informative product ions were observed. Using a triple-stage quadrupole instrument, selected reaction monitoring analyses by monitoring characteristic transition ions allowed the achievement of a highly sensitive and specific assay. This method was used to determine whether the 3-sulfates of the bile acid-GSH conjugates (BA-GSH) were formed when BA-GSH were incubated with a rat liver cytosolic fraction to which 3'-phosphoadenosine 5'-phosphosulfate had been added. The S-acyl linkage was rapidly hydrolyzed to form the unconjugated bile acid. A little sulfation of the GSH conjugates occurred, but greater sulfation at C-3 of the liberated bile acid occurred. Sulfation was proportional to the hydrophobicity of the unconjugated bile acid. Thus GSH conjugates of bile acids as well as their C-3 sulfates if formed in vivo are rapidly hydrolyzed by cytosolic enzymes. (C) 2012 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2012.02.001
• 作为产物：
  描述：

  3alpha,7beta-Dihydroxy-5alpha-cholan-24-oic Acid 生成 7-hydroxy-3-(sulfooxy)-(3α,5β,7β)-cholan-24-oic acid
  参考文献：
  名称：

  BANDIERA, T.;ALBINI, F. M.;ALBINI, E., SYNTH. COMMUN., 17,(1987) N 9, 1111-1117

  摘要：

  DOI：

文献信息

• Bandiera, Tiziano; Albini, Franca Marione; Albini, Enrico, Synthetic Communications, 1987, vol. 17, # 9, p. 1111 - 1118
  作者：Bandiera, Tiziano、Albini, Franca Marione、Albini, Enrico

  DOI：——

  日期：——
• Synthesis of the 3-sulfates of S-acyl glutathione conjugated bile acids and their biotransformation by a rat liver cytosolic fraction
  作者：Kuniko Mitamura、Naohiro Hori、Shiori Mino、Takashi Iida、Alan F. Hofmann、Shigeo Ikegawa

  DOI：10.1016/j.chemphyslip.2012.02.001

  日期：2012.4

  The 3-sulfates of the S-acyl glutathione (GSH) conjugates of five natural bile acids (cholic, chenodeoxycholic, deoxycholic, ursodeoxycholic, and lithocholic) were synthesized as reference standards in order to investigate their possible formation by a rat liver cytosolic fraction. Their structures were confirmed by proton nuclear magnetic resonance, as well as by means of electrospray ionization-linear ion-trap mass spectrometry with negative-ion detection. Upon collision-induced dissociation, structurally informative product ions were observed. Using a triple-stage quadrupole instrument, selected reaction monitoring analyses by monitoring characteristic transition ions allowed the achievement of a highly sensitive and specific assay. This method was used to determine whether the 3-sulfates of the bile acid-GSH conjugates (BA-GSH) were formed when BA-GSH were incubated with a rat liver cytosolic fraction to which 3'-phosphoadenosine 5'-phosphosulfate had been added. The S-acyl linkage was rapidly hydrolyzed to form the unconjugated bile acid. A little sulfation of the GSH conjugates occurred, but greater sulfation at C-3 of the liberated bile acid occurred. Sulfation was proportional to the hydrophobicity of the unconjugated bile acid. Thus GSH conjugates of bile acids as well as their C-3 sulfates if formed in vivo are rapidly hydrolyzed by cytosolic enzymes. (C) 2012 Elsevier Ireland Ltd. All rights reserved.
• BANDIERA, T.;ALBINI, F. M.;ALBINI, E., SYNTH. COMMUN., 17,(1987) N 9, 1111-1117
  作者：BANDIERA, T.、ALBINI, F. M.、ALBINI, E.

  DOI：——

  日期：——