N-[(3alpha,5beta,7beta,8Xi,9Xi,14Xi)-3,7-二羟基-24-氧代胆烷-24-基]-N-甲基甘氨酸 | 88446-87-1

• 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: N-[(3alpha,5beta,7beta,8Xi,9Xi,14Xi)-3,7-二羟基-24-氧代胆烷-24-基]-N-甲基甘氨酸
• 中文别名: α-氰基-α-羟基-3-苯氧基苯甲基乙酸酯
• 英文名称: sarcoursodeoxycholic acid
• 英文别名: ursodeoxycholylsarcosine；2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]-methylamino]acetic acid
• CAS: 88446-87-1
• 化学式: C₂₇H₄₅NO₅
• 分子量: 463.658
• InChiKey: YZYBIGOLMMAZFK-IMLYGNJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  肌氨酸 、 熊去氧胆酸 在 sodium hydroxide 、 三正丁胺 、 氯甲酸乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以15.1 g的产率得到N-[(3alpha,5beta,7beta,8Xi,9Xi,14Xi)-3,7-二羟基-24-氧代胆烷-24-基]-N-甲基甘氨酸
  参考文献：
  名称：

  Synthesis, intestinal absorption and metabolism of sarcosine conjugated ursodeoxycholic acid

  摘要：

  Sarcosine conjugated ursodeoxycholic acid (SUDC) was synthesized and its intestinal absorption and metabolism were studied in rat and hamster. Intestinal absorption study using bile fistula rat shows that more than 90% of SUDC administered intraduodenally was excreted in the bile within 24 hr. No change of the administered bile acid was seen during the absorption from the intestine, the passage of the liver, and the excretion into the bile. When [24-14C]SUDC and [11,12-3H2]-ursodeoxycholic acid were administered orally to a hamster, more than 95% of both the administered 14C and 3H were recovered from the feces within 6 days. Most (77%) of the fecal 14C-labeled compound was SUDC, whereas 95% of the fecal 3H-labeled compound was unconjugated lithocholic acid. These results indicate that SUDC, unlike taurine or glycine conjugated bile acid, resists bacterial deconjugation and 7-dehydroxylation.

  DOI：

  10.1016/0039-128x(84)90030-8