3-Β,5-Α,6-Β-三羟基胆酸 | 16030-92-5

• 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
• 中文名称: 3-Β,5-Α,6-Β-三羟基胆酸
• 英文名称: 3β,5α,6β-trihydroxy-cholest-24-oic-acid
• 英文别名: 3β,5α,6β-trihydroxycholanoic acid；3β,5,6β-trihydroxy-5α-cholanoic acid-(24)；3β,5,6β-Trihydroxy-5α-cholansaeure-(24)；3beta,5alpha,6beta-Trihydroxycholan-24-oic Acid；(4R)-4-[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-3,5,6-trihydroxy-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 16030-92-5
• 化学式: C₂₄H₄₀O₅
• 分子量: 408.579
• InChiKey: NMKAZCXSXYNCFW-DWQVTILUSA-N

物化性质

• 沸点：
  560.2±40.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Β,5-Α,6-Β-三羟基胆酸 以 甲醇 为溶剂， 以0.98 g的产率得到3β,5α,6β,19-tetrahydroxyl-cholest-24-oic-acid
  参考文献：
  名称：

  Design and synthesis of polyhydroxy steroids as selective inhibitors against AKR1B10 and molecular docking

  摘要：

  AKR1B10 is a member of the human aldo-keto reductase superfamily which is highly expressed in several types of cancers, and has been regarded as a promising cancer therapeutic target. In this paper, a series of polyhydroxy steroids were designed and synthesized to selectively inhibit AKR1B10 activity. The most selective compound, novel compound 6, has an IC50 of 0.83 +/- 0.07 mu M and a selectivity of more than 120-fold for AKR1B10/AKR1B1. Structure-activity relation analyses indicate that hydroxyl at C-19 can significantly improve the selective inhibition of AKR1B10. The binding mode of AKR1B10 and its inhibitors were studied. (C) 2016 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2016.03.004
• 作为产物：
  描述：

  3B-羟基-D5-胆烯酸 在 甲酸 作用下， 以 甲醇 为溶剂， 反应 3.08h， 生成 3-Β,5-Α,6-Β-三羟基胆酸
  参考文献：
  名称：

  Design and synthesis of polyhydroxy steroids as selective inhibitors against AKR1B10 and molecular docking

  摘要：

  AKR1B10 is a member of the human aldo-keto reductase superfamily which is highly expressed in several types of cancers, and has been regarded as a promising cancer therapeutic target. In this paper, a series of polyhydroxy steroids were designed and synthesized to selectively inhibit AKR1B10 activity. The most selective compound, novel compound 6, has an IC50 of 0.83 +/- 0.07 mu M and a selectivity of more than 120-fold for AKR1B10/AKR1B1. Structure-activity relation analyses indicate that hydroxyl at C-19 can significantly improve the selective inhibition of AKR1B10. The binding mode of AKR1B10 and its inhibitors were studied. (C) 2016 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2016.03.004

文献信息

• Bile acid biomarkers for Niemann-Pick diseases, methods and uses therefor
  申请人：Ory Daniel

  公开号：US10983112B2

  公开（公告）日：2021-04-20

  Methods for identification and quantification of bile acids are disclosed. Bile acids in plasma, serum and/or blood such as a dried blood spot are used to identify subjects with a Niemann-Pick disease. The methods include measuring levels of a bile acid, such as 3β,5α,6β-trihydroxycholanic acid, N-(3β,5α,6β-trihydroxy-cholan-24-oyl)glycine, N-(3β,5α,6β-trihydroxy-cholan-24-oyl)taurine, or a combination thereof. Detection of bile acids involve mass spectroscopy and/or a combination of mass spectroscopy and liquid chromatography such as a LC-MS/MS assay. The methods can be used with sphingomyelinase assays to detect, diagnose and differentiate between Niemann-Pick A/B and Niemann-Pick C (NPC) disease.

  本研究公开了胆汁酸的鉴定和定量方法。血浆、血清和/或血液（如干血斑）中的胆汁酸可用于鉴定患有尼曼-皮克病的受试者。这些方法包括测量胆汁酸的水平，如 3β,5α,6β-三羟基胆烷酸、N-(3β,5α,6β-三羟基-胆烷-24-酰基)甘氨酸、N-(3β,5α,6β-三羟基-胆烷-24-酰基)牛磺酸或它们的组合。胆汁酸的检测涉及质谱法和/或质谱法与液相色谱法（如 LC-MS/MS 分析法）的结合。这些方法可与鞘磷脂酶测定法一起用于检测、诊断和区分尼曼-皮克病 A/B 和尼曼-皮克病 C (NPC)。
• Hattori, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 32,40, 41; dtsch. Ref. S. 12
  作者：Hattori

  DOI：——

  日期：——
• BILE ACID BIOMARKERS FOR NIEMANN-PICK DISEASES, METHODS AND USES THEREFOR
  申请人：Washington University

  公开号：EP3387433A1

  公开（公告）日：2018-10-17
• [EN] BILE ACID BIOMARKERS FOR NIEMANN-PICK DISEASES, METHODS AND USES THEREFOR<br/>[FR] BIOMARQUEURS D'ACIDE BILIAIRE POUR LES MALADIES DE NIEMANN-PICK, LEURS PROCÉDÉS ET LEURS UTILISATIONS
  申请人：UNIV WASHINGTON

  公开号：WO2016069759A1

  公开（公告）日：2016-05-06

  Methods for identification and quantification of bile acids are disclosed. Bile acids in plasma, serum and/or blood such as a dried blood spot are used to identify subjects with a Niemann-Pick disease. The methods include measuring levels of a bile acid, such as 3β,5α,6β-trihydroxycholanic acid, N-(3β,5α,6β-trihydroxy-cholan-24-oyl)glycine, N-(3β,5α,6β-trihydroxy-cholan-24-oyl)taurine, or a combination thereof. Detection of bile acids involve mass spectroscopy and/or a combination of mass spectroscopy and liquid chromatography such as a LC-MS/MS assay. The methods can be used with sphingomyelinase assays to detect, diagnose and differentiate between Niemann-Pick A/B and Niemann-Pick C (NPC) disease.
• Design and synthesis of polyhydroxy steroids as selective inhibitors against AKR1B10 and molecular docking
  作者：Wenli Chen、Xinying Chen、Shujia Zhou、Hong Zhang、Ling Wang、Jun Xu、Xiaopeng Hu、Wei Yin、Guangmei Yan、Jingxia Zhang

  DOI：10.1016/j.steroids.2016.03.004

  日期：2016.6

  AKR1B10 is a member of the human aldo-keto reductase superfamily which is highly expressed in several types of cancers, and has been regarded as a promising cancer therapeutic target. In this paper, a series of polyhydroxy steroids were designed and synthesized to selectively inhibit AKR1B10 activity. The most selective compound, novel compound 6, has an IC50 of 0.83 +/- 0.07 mu M and a selectivity of more than 120-fold for AKR1B10/AKR1B1. Structure-activity relation analyses indicate that hydroxyl at C-19 can significantly improve the selective inhibition of AKR1B10. The binding mode of AKR1B10 and its inhibitors were studied. (C) 2016 Published by Elsevier Inc.