7,12-dihydroxy-3-(sulfooxy)(3α,5β,7α,12α)-cholan-24-oic acid

• 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: 7,12-dihydroxy-3-(sulfooxy)(3α,5β,7α,12α)-cholan-24-oic acid
• 英文别名: cholic acid 3-sulfate；3-sulfocholic acid；cholic Acid 3-O-sulfate；CA-3S；(4R)-4-[(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-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
• 化学式: C₂₄H₄₀O₈S
• 分子量: 488.643
• InChiKey: AUVYDCOKXDDYKR-OELDTZBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 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：
  150
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7,12-dihydroxy-3-(sulfooxy)(3α,5β,7α,12α)-cholan-24-oic acid 在 盐酸 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 胆酸
  参考文献：
  名称：

  Determination of sulfated and nonsulfated bile acids in serum by mass fragmentography

  摘要：

  A Sep-Pak C18 cartridge was used for purification of bile acids from serum. Three kinds of deuterium labeled internal standards were required for accurate measurement of individual sulfated and nonsulfated bile acids. These internal standards were added to the serum before its application to the cartridge. Separation of sulfated and nonsulfated bile acids was performed on piperidinohydroxypropyl Sephadex LH-20 column chromatography. The nonsulfate fraction was submitted to alkaline hydrolysis, and the sulfate fraction to solvolysis followed by alkaline hydrolysis. Each fraction was converted to the hexafluoroisopropyl-trifluoroacetyl derivatives and quantitated by mass fragmentography. The recovery of each bile acid sulfate was quite satisfactory. In fasting healthy subjects the mean of total nonsulfated bile acids in serum was 1.324 micrograms/ml, and that of total sulfated bile acids was 0.450 micrograms/ml. Sulfated lithocholic acid comprised a large part of sulfated bile acids in healthy subjects.

  DOI：

  10.1016/0039-128x(83)90121-6
• 作为产物：
  描述：

  胆酸甲酯 在 吡啶 、 4-二甲氨基吡啶 、 三氧化硫吡啶 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 26.0h， 生成 7,12-dihydroxy-3-(sulfooxy)(3α,5β,7α,12α)-cholan-24-oic acid
  参考文献：
  名称：

  利用利福平给药的食蟹猕猴鉴定胆汁酸3-O-硫酸盐结合物，作为有机阴离子转运多肽的潜在新型生物标志物。

  摘要：

  在寻找肝脏有机阴离子转运多肽（OATP）的新型胆汁酸（BA）生物标志物时，食蟹猕猴接受了四种剂量水平（1、3、10和30 mg / kg）的口服利福平（RIF），产生血浆无Cmax值（分别为0.06、0.66、2.57和7.79 µM），跨越了报告的OATP1B1和OATP1B3的体外IC50值（≤1.7μM）。如预期的那样，OATP探针药物（静脉注射2H4-匹伐他汀，0.2 mg / kg）的血浆浓度-时间曲线（AUC）下面积分别增加了1.2倍，2.4倍，3.8倍和4.5倍。对RIF食蟹猴的血浆进行液相色谱-串联质谱分析，该方法可支持30种不同BA的分析。对猴尿进行了分析，我们还确定了RIF对BA肾清除率的影响微乎其微。尽管硫酸化的BA仅占血浆BA池的1％，但观察到五个BA的硫酸盐具有强健的RIF剂量响应（血浆AUC的最大≥50倍增加）[糖去氧胆酸（GDCA-S），糖去氧胆酸（GCDCA-S

  DOI：

  10.1124/dmd.117.075275

文献信息

• [EN] HEME OXYGENASE-1 INDUCER AND APPLICATION THEREOF<br/>[FR] INDUCTEUR DE L'HÈME OXYGÉNASE-1 ET SON APPLICATION<br/>[ZH] 血红素氧合酶-1诱导剂及其应用
  申请人：NAT INSTITUTE OF BIOLOGICAL SCIENCES BEIJING

  公开号：WO2020238832A1

  公开（公告）日：2020-12-03

  本发明涉及血红素氧合酶-1诱导剂，所述诱导剂为如通式I所示的化合物或其盐。本发明提供的新型血红素氧合酶-1诱导剂可以高效诱导血红素氧合酶-1的表达，安全性高、副作用小，且在炎症相关疾病的预防和治疗领域具有广泛的应用价值。
• 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.
• SYNTHETIC DERIVATIVES OF CHOLIC ACID 7-SULFATE AND USES THEREOF
  申请人：President and Fellows of Harvard College

  公开号：EP3890745A1

  公开（公告）日：2021-10-13
• COMPOSITIONS AND METHODS RELATED TO CHOLIC ACID 7-SULFATE AS A TREATMENT FOR DIABETES
  申请人：President and Fellows of Harvard College

  公开号：US20210315908A1

  公开（公告）日：2021-10-14

  Provided are methods of treating diabetes and/or obesity in a subject in need thereof, and methods of increasing the amount of cholic acid-7-sulfate (CA7S) in a subject. Further provided herein are methods of administering CA7S to a subject. Also provided are compositions and kits comprising cholic acid-7-sulfate, or a salt thereof for use in the treatment of diabetes and/or obesity.
• US5585255A
  申请人：——

  公开号：US5585255A

  公开（公告）日：1996-12-17