3alpha,7alpha-Dihydroxycoprostanic acid (BioDeep_00000005565)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

化学式: C27H46O4 (434.3395916)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 0.16%

分子结构信息

SMILES: CC(CCCC(C)C(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
InChI: InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1

描述信息

3α,7α-Dihydroxycoprostanic acid is a bile acid excreted in small amounts in the urine of healthy subjects (PMID: 864325). 3α,7α-Dihydroxycoprostanic acid is the precursor to chenodeoxycholic acid, 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.
3a,7a-Dihydroxycoprostanic acid is a bile acid excreted in small amounts in the urine of healthy subjects (PMID 864325)

同义名列表

36 个代谢物同义名

(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid; (3alpha,5beta,7alpha)-3,7-Dihydroxycholestan-26-Oic acid; 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oic acid; 3α,7α-Dihydroxy-5β-cholestanoate; 3α,7α-Dihydroxy-5β-cholestanate; 3alpha,7alpha-Dihydroxy-5beta-cholestanoic acid; 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oate; 3alpha,7alpha-Dihydroxy-5beta-cholestanic acid; 3alpha,7alpha-Hydroxy-5β-cholestan-26-Oic acid; (3a,5b,7a)-3,7-Dihydroxycholestan-26-Oic acid; (3Α,5β,7α)-3,7-dihydroxycholestan-26-Oic acid; 3alpha,7alpha-Dihydroxy-5beta-cholestanoate; 3alpha,7alpha-Dihydroxy-5beta-cholestanate; 3a,7a-Dihydroxy-5b-cholestan-26-Oic acid; 3Α,7α-dihydroxy-5β-cholestan-26-Oic acid; 3alpha,7alpha-Dihydroxycoprostanic acid; 3a,7a-Hydroxy-5β-cholestan-26-Oic acid; 3a,7a-Hydroxy-5b-cholestan-26-Oic acid; 3Α,7α-hydroxy-5β-cholestan-26-Oic acid; 3a,7a-Dihydroxy-5b-cholestanoic acid; 3Α,7α-dihydroxy-5β-cholestan-26-Oate; 3Α,7α-dihydroxy-5β-cholestanoic acid; 3a,7a-Dihydroxy-5b-cholestan-26-Oate; 3Α,7α-dihydroxy-5β-cholestanic acid; 3alpha,7alpha-Dihydroxycoprostanate; 3a,7a-Dihydroxy-5b-cholestanic acid; 3a,7a-Hydroxy-5b-cholestan-26-Oate; 3Α,7α-dihydroxy-5β-cholestanoate; 3a,7a-Dihydroxy-5b-cholestanoate; 3Α,7α-dihydroxy-5β-cholestanate; 3a,7a-Dihydroxy-5b-cholestanate; 3a,7a-Dihydroxycoprostanic acid; 3Α,7α-dihydroxycoprostanic acid; 3,7-Dihydroxycoprostanic acid; 3a,7a-Dihydroxycoprostanate; 3Α,7α-dihydroxycoprostanate



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(0)

PlantCyc(0)

代谢反应

101 个相关的代谢反应过程信息。

Reactome(78)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(22)

PharmGKB(0)

2 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。



文献列表

  • D W Johnson, H J ten Brink, R C Schuit, C Jakobs. Rapid and quantitative analysis of unconjugated C(27) bile acids in plasma and blood samples by tandem mass spectrometry. Journal of lipid research. 2001 Jan; 42(1):9-16. doi: NULL. [PMID: 11160360]
  • S Ferdinandusse, H Overmars, S Denis, H R Waterham, R J Wanders, P Vreken. Plasma analysis of di- and trihydroxycholestanoic acid diastereoisomers in peroxisomal alpha-methylacyl-CoA racemase deficiency. Journal of lipid research. 2001 Jan; 42(1):137-41. doi: 10.1016/s0022-2275(20)32345-2. [PMID: 11160375]
  • M Une, A Inoue, T Kurosawa, M Tohma, T Hoshita. Identification of (24E)-3 alpha,7 alpha-dihydroxy-5 beta-cholest-24-enoic acid and (24R,25S)-3 alpha,7 alpha,24-trihydroxy-5 beta-cholestanoic acid as intermediates in the conversion of 3 alpha,7 alpha-dihydroxy-5 beta-cholestanoic acid to chenodeoxycholic acid in rat liver homogenates. Journal of lipid research. 1994 Apr; 35(4):620-4. doi: 10.1016/s0022-2275(20)41175-7. [PMID: 8006516]
  • A K Farrants, A Nilsson, J I Pedersen. Human hepatoblastoma cells (HepG2) and rat hepatoma cells are defective in important enzyme activities in the oxidation of the C27 steroid side chain in bile acid formation. Journal of lipid research. 1993 Dec; 34(12):2041-50. doi: . [PMID: 8301225]
  • A K Batta, R Mirchandani, G Salen, S Shefer. Synthesis of 3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid from 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestan-26-oic acid: configuration in the bile of Alligator mississippiensis. Steroids. 1992 Apr; 57(4):162-6. doi: 10.1016/0039-128x(92)90002-q. [PMID: 1519259]
  • R J Wanders, M Casteels, G P Mannaerts, C W van Roermund, R B Schutgens, V Kozich, J Zeman, J Hyanek. Accumulation and impaired in vivo metabolism of di- and trihydroxycholestanoic acid in two patients. Clinica chimica acta; international journal of clinical chemistry. 1991 Oct; 202(3):123-32. doi: 10.1016/0009-8981(91)90043-c. [PMID: 1839974]
  • B F Kase, J I Pedersen, K O Wathne, J Gustafsson, I Björkhem. Importance of peroxisomes in the formation of chenodeoxycholic acid in human liver. Metabolism of 3 alpha,7 alpha-dihydroxy-5 beta-cholestanoic acid in Zellweger syndrome. Pediatric research. 1991 Jan; 29(1):64-9. doi: 10.1203/00006450-199101000-00013. [PMID: 2000261]
  • J Goto, H Miura, T Nambara. Studies on steroids. CCXXXXV. Determination of 5 beta-cholestanoic acids in human urine by gas chromatography-mass spectrometry with negative ion chemical ionization detection. Journal of chromatography. 1989 Sep; 493(2):245-55. doi: NULL. [PMID: 2584293]
  • M Axelson, B Mörk, J Sjövall. Occurrence of 3 beta-hydroxy-5-cholestenoic acid, 3 beta,7 alpha-dihydroxy-5-cholestenoic acid, and 7 alpha-hydroxy-3-oxo-4-cholestenoic acid as normal constituents in human blood. Journal of lipid research. 1988 May; 29(5):629-41. doi: 10.1016/s0022-2275(20)38509-6. [PMID: 3411238]
  • K Prydz, B F Kase, I Björkhem, J I Pedersen. Formation of chenodeoxycholic acid from 3 alpha, 7 alpha-dihydroxy-5 beta-cholestanoic acid by rat liver peroxisomes. Journal of lipid research. 1986 Jun; 27(6):622-8. doi: ". [PMID: 3746130]
  • O W Cass, G C Williams, R F Hanson. Competitive inhibition of side chain oxidation of 3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid by 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oic acid in the hamster. Journal of lipid research. 1980 Feb; 21(2):186-91. doi: 10.1016/s0022-2275(20)39824-2. [PMID: 7373160]