Ursocholic acid (BioDeep_00000415916)

Main id: BioDeep_00000014386

 

PANOMIX_OTCML-2023 Bile acids


代谢物信息卡片


3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-oic Acid

化学式: C24H40O5 (408.28755900000004)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(urine) 0.27%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])C[C@H](O)[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])[C@@H](O)C[C@]2([H])C[C@H](O)C1
InChI: InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1

描述信息

A bile acid that is 5beta-cholan-24-oic acid bearing three hydroxy substituents at positions 3alpha, 7beta and 12alpha.
D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts
D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
Ursocholic acid, a bile acid found predominantly in bile of mammals, is transformed into deoxycholic acid by the intestinal microflora in mice. Ursodeoxycholic acid is an inhibitor of 7α-hydroxysteroid dehydrogenase and hepatocyte nuclear factor 1α[1].

同义名列表

3 个代谢物同义名

Ursocholic acid; 3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-oic Acid; ST 24:1;O5



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

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INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

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文献列表

  • Maria Luisa Balmer, Kathrin Siegrist, Arthur Zimmermann, Jean-François Dufour. Effects of ursodeoxycholic acid in combination with vitamin E on adipokines and apoptosis in patients with nonalcoholic steatohepatitis. Liver international : official journal of the International Association for the Study of the Liver. 2009 Sep; 29(8):1184-8. doi: 10.1111/j.1478-3231.2009.02037.x. [PMID: 19422479]
  • Susana Cuesta de Juan, Maria J Monte, Rocio I R Macias, Valérie Wauthier, Pedro Buc Calderon, Jose J G Marin. Ontogenic development-associated changes in the expression of genes involved in rat bile acid homeostasis. Journal of lipid research. 2007 Jun; 48(6):1362-70. doi: 10.1194/jlr.m700034-jlr200. [PMID: 17332599]
  • Ashok K Batta, Gerald Salen, G Stephen Tint. Hydrophilic 7 beta-hydroxy bile acids, lovastatin, and cholestyramine are ineffective in the treatment of cerebrotendinous xanthomatosis. Metabolism: clinical and experimental. 2004 May; 53(5):556-62. doi: 10.1016/j.metabol.2003.12.003. [PMID: 15131757]
  • T Nakashima, T Yoh, Y Sumida, Y Kakisaka, H Mitsuyoshi. Differences in the efficacy of ursodeoxycholic acid and bile acid metabolism between viral liver diseases and primary biliary cirrhosis. Journal of gastroenterology and hepatology. 2001 May; 16(5):541-7. doi: 10.1046/j.1440-1746.2001.02485.x. [PMID: 11350551]
  • T Nakashima, Y Sakamoto, K Inaba, H Mitsuyoshi, H Ishikawa, Y Nakajima, M Sakai, T Shima, K Kashima. A paucity of unusual trihydroxy bile acids in the urine of patients with severe liver diseases. Hepatology (Baltimore, Md.). 1999 May; 29(5):1518-22. doi: 10.1002/hep.510290502. [PMID: 10216137]
  • A K Batta, G Salen, J Abroon. Ursocholic acid, a hydrophilic bile acid, fails to improve liver function parameters in primary biliary cirrhosis: comparison with ursodeoxycholic acid. The American journal of gastroenterology. 1997 Jun; 92(6):1035-7. doi: NULL. [PMID: 9177526]
  • G S Tint, A K Batta, B Dayal, N Kovell, S Shefer, G Salen. Metabolism of ursocholic acid in humans: conversion of ursocholic acid to deoxycholic acid. Hepatology (Baltimore, Md.). 1992 Apr; 15(4):645-50. doi: 10.1002/hep.1840150415. [PMID: 1551642]
  • B Dayal, G Salen. Stereospecific synthesis and two-dimensional 1H-NMR investigation of isoursocholic acid. Journal of lipid research. 1991 Aug; 32(8):1381-7. doi: 10.1016/s0022-2275(20)41968-6. [PMID: 1770320]
  • K Uchida, T Akiyoshi, H Igimi, H Takase, Y Nomura, S Ishihara. Differential effects of ursodeoxycholic acid and ursocholic acid on the formation of biliary cholesterol crystals in mice. Lipids. 1991 Jul; 26(7):526-30. doi: 10.1007/bf02536598. [PMID: 1943496]
  • A Roda, A Minutello, M A Angellotti, A Fini. Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research. 1990 Aug; 31(8):1433-43. doi: . [PMID: 2280184]
  • A Lanzini, G Pigozzi, D Facchinetti, L Bettini, M Castellano, M Beschi, A Rossi, G Muiesan. Effect of chronic ursocholic acid administration on bile lipid composition and bile acid pool size in gallstone patients. Scandinavian journal of gastroenterology. 1990 Jul; 25(7):711-9. doi: 10.3109/00365529008997597. [PMID: 2396085]
  • P J Howard, D Gleeson, G M Murphy, R H Dowling. Ursocholic acid: bile acid and bile lipid dose response and clinical studies in patients with gall stones. Gut. 1989 Jan; 30(1):97-103. doi: 10.1136/gut.30.1.97. [PMID: 2920932]
  • A Roda, R Aldini, B Grigolo, P Simoni, E Roda, R Pellicciari, P L Lenzi, B Natalini. 23-Methyl-3 alpha,7 beta-dihydroxy-5 beta-cholan-24-oic acid: dose-response study of biliary secretion in rat. Hepatology (Baltimore, Md.). 1988 Nov; 8(6):1571-6. doi: 10.1002/hep.1840080617. [PMID: 3192170]
  • S Kuroki, E H Mosbach, B I Cohen, C K McSherry. Metabolism of the bile acid analogues 7 beta-methyl-cholic acid and 7 alpha-methyl-ursocholic acid. Gastroenterology. 1987 Apr; 92(4):876-84. doi: 10.1016/0016-5085(87)90960-7. [PMID: 3556995]
  • T Nakashima, A Sano, Y Seto, T Nakajima, Y Nakagawa, T Okuno, T Takino, T Hasegawa. Unusual trihydroxy bile acids in the urine of healthy humans. Clinica chimica acta; international journal of clinical chemistry. 1986 Oct; 160(1):47-53. doi: 10.1016/0009-8981(86)90334-7. [PMID: 3769218]
  • B Borgström, L Krabisch, M Lindström, J Lillienau, T Midtvedt, M Corrie. Effects of feeding ursocholic acid to germfree rats. Scandinavian journal of clinical and laboratory investigation. 1986 Apr; 46(2):183-7. doi: 10.3109/00365518609083656. [PMID: 3715370]
  • P Loria, N Carulli, G Medici, D Menozzi, G Salvioli, M Bertolotti, M Montanari. Effect of ursocholic acid on bile lipid secretion and composition. Gastroenterology. 1986 Apr; 90(4):865-74. doi: 10.1016/0016-5085(86)90862-0. [PMID: 3949116]
  • J D Sutherland, L V Holdeman, C N Williams, I A Macdonald. Formation of urso- and ursodeoxy-cholic acids from primary bile acids by a Clostridium limosum soil isolate. Journal of lipid research. 1984 Oct; 25(10):1084-9. doi: . [PMID: 6512414]
  • Y Amuro, E Hayashi, T Endo, K Higashino, S Kishimoto. Unusual trihydroxylated bile acids in urine of patients with liver cirrhosis. Clinica chimica acta; international journal of clinical chemistry. 1983 Jan; 127(1):61-7. doi: 10.1016/0009-8981(83)90075-x. [PMID: 6825311]
  • J D Sutherland, I A Macdonald. The metabolism of primary, 7-oxo, and 7 beta-hydroxy bile acids by Clostridium absonum. Journal of lipid research. 1982 Jul; 23(5):726-32. doi: 10.1016/s0022-2275(20)38105-0. [PMID: 7119570]
  • I A Macdonald, D M Hutchison, T P Forrest. Formation of urso- and ursodeoxy-cholic acids from primary bile acids by Clostridium absonum. Journal of lipid research. 1981 Mar; 22(3):458-66. doi: 10.1016/s0022-2275(20)34960-9. [PMID: 6940948]