Ursocholic acid (BioDeep_00000014386)

 

Secondary id: BioDeep_00000415916

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Bile acids PANOMIX LipidSearch


代谢物信息卡片


(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

化学式: C24H40O5 (408.2876)
中文名称: 熊胆酸, 熊果胆酸
谱图信息: 最多检出来源 Homo sapiens(blood) 21.06%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Ursocholic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/ursocholic_acid (retrieved 2025-01-03) (BioDeep RN: BioDeep_00000014386). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(C3(C)4)([H])(CC(O)CC4)CC(C(C3([H])2)(C(C1(C)C(O)C2)([H])CCC1([H])C(C)CCC(O)=O)[H])O
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

Ursocholic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487, 16037564, 12576301, 11907135). Ursocholic acid is the 7 beta-hydroxyepimer of cholic acid. It induces a reduction of bile cholesterol saturation.
A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12.

Ursocholic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2955-27-3 (retrieved 2024-07-16) (CAS RN: 2955-27-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
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

37 个代谢物同义名

(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid; (3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid; 3α,7β,12α-Trihydroxy-5β-cholan-24-oic Acid; (3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oate; 3 alpha,7 beta,12 alpha-Trihydroxy-5 beta-cholan-24-Oic acid; 3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-oic Acid; 3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oate; 3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acid; (3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oic acid; (3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oic acid; 3alpha,7beta,12alpha-Trihydroxy-5beta-cholanate; (3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oate; (3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oate; 3Α,7β,12α-trihydroxy-5β-cholan-24-Oic acid; 3a,7b,12a-Trihydroxy-5b-cholan-24-Oic acid; 3a,7b,12a-Trihydroxy-5b-cholanoic acid; 3a,7b,12a-Trihydroxy-5b-cholan-24-Oate; 3Α,7β,12α-trihydroxy-5β-cholan-24-Oate; 3Α,7β,12α-trihydroxy-5β-cholanic acid; 3a,7b,12a-Trihydroxy-5b-cholanic acid; 3a,7b,12a-Trihydroxy-5b-cholanoate; 3Α,7β,12α-trihydroxy-5β-cholanate; 3a,7b,12a-Trihydroxycholanic acid; 3a,7b,12a-Trihydroxy-5b-cholanate; 3a,7b,12a-Trihydroxycholanate; 7beta-Hydroxyisocholic acid; 7b-Hydroxyisocholic acid; 7Β-hydroxyisocholic acid; 7beta-Hydroxyisocholate; 7Β-hydroxyisocholate; 7b-Hydroxyisocholate; 7-Epicholic acid; Ursocholic acid; 7-Epicholate; Ursocholate; Ursocholic acid (UCA); Ursocholate



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


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]