Details of Metabolite (Meta)

General Information of Metabolite (ID: MT002)
  Meta Name
beta-muricholate
  Unify Name
3a,6b,7b-Trihydroxy-5b-cholanoic acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oic acid;3,6,7-Trihydroxy-5beta-cholan-24-Oic acid;5beta-Cholanic acid-3alpha,6beta,7beta-triol;beta-MCA;beta-Muricholic acid;3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oic acid;(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oate;(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oic acid;(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oate;(3Alpha,5beta,6beta,7beta)-3,6,7-trihydroxycholan-24-Oate;(3Alpha,5beta,6beta,7beta)-3,6,7-trihydroxycholan-24-Oic acid;3,6,7-Trihydroxy-5b-cholan-24-Oate;3,6,7-Trihydroxy-5b-cholan-24-Oic acid;3,6,7-Trihydroxy-5beta-cholan-24-Oate;3,6,7-Trihydroxy-5beta-cholan-24-Oate;3,6,7-Trihydroxy-5beta-cholan-24-Oic acid;5b-Cholanate-3a,6b,7b-triol;5b-Cholanic acid-3a,6b,7b-triol;5beta-Cholanate-3alpha,6beta,7beta-triol;5beta-cholanate-3Alpha,6beta,7beta-triol;5beta-cholanic acid-3Alpha,6beta,7beta-triol;b-MCA;beta-mca;b-Muricholate;b-Muricholic acid;beta-Muricholate;beta-muricholate;beta-muricholic acid;3a,6b,7b-Trihydroxy-5b-cholan-24-Oate;3a,6b,7b-Trihydroxy-5b-cholan-24-Oic acid;3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oate;3Alpha,6beta,7beta-trihydroxy-5beta-cholan-24-Oate;3Alpha,6beta,7beta-trihydroxy-5beta-cholan-24-Oic acid;3a,6b,7b-Trihydroxy-5b-cholanoate;3a,6b,7b-Trihydroxy-5b-cholanate;3a,6b,7b-Trihydroxy-5b-cholanic acid;3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid;3,6,7-Trihydroxy-5-cholanoic acid;alpha-Muricholic acid;Hyocholic acid;Muricholic acid;Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer;Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer;Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer;Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer;Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer;Muricholic acid, sodium salt;Omega-muricholic acid;Trihydroxy-5 alpha-cholanoic acid
  Molecule Type
Bile acids (BAs)
  Formula
C24H40O5
  Inchi Key
DKPMWHFRUGMUKF-CRKPLTDNSA-N
  Description    Click to Show/Hide the Detailed Description of This Metabolite
3a,6b,7b-Trihydroxy-5b-cholanoic acid is a bile acid found in urine exhibiting a complex modification pattern, including free, glyco- and sulfoconjugated forms (PMID 3834660 ). 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 ).
  External Links   HMDB ID   HMDB0000415
  KEGG ID   C17726
  Metlin ID   5404

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
Histone Deacetylation HDAC EM Info . . . [1], [2]

The microbes that produce this metabolite
      Bacteroides
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [4]
         Description
Bacteroides is a genus of gram-negative, obligate anaerobic bacteria.
      Eubacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Eubacteria is a genus of gram-positive bacteria in the family Eubacteriaceae. These bacteria are characterised by a rigid cell wall. They may either be motile or nonmotile. If motile, they have a flagellum. A typical flagellum consists of a basal body, filament, and hook. The long filament is the organ which helps eubacteria move.
      Clostridium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Clostridium is a genus of gram-positive, anaerobic bacteria from the family Bacillaceae.
      Bifidobacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Bifidobacteria is a genus of gram-positive, nonmotile, often branched anaerobic bacteria. They are ubiquitous inhabitants of the gastrointestinal tract, vagina and mouth of mammals, including humans.
      Enterobacter
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Enterobacter is a genus of common gram-negative, facultatively anaerobic, rod-shaped, non-spore-forming bacteria of the family Enterobacteriaceae. It is the type genus of the order Enterobacterales.
      Escherichia
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Escherichia is a genus of gram-negative, non-spore-forming, facultatively anaerobic, rod-shaped bacteria from the family Enterobacteriaceae.
      Lactobacillus
         Detailed Information MIC Info click to show the detail information of this Microbiota [5], [1]
         Description
Lactobacillus is a genus of gram-positive, facultative anaerobic or microaerophilic, rod-shaped, non-spore-forming bacteria. They are a major part of the lactic acid bacteria group. In humans, they constitute a significant component of the microbiota at a number of body sites, such as the digestive system, urinary system, and genital system.

References
1 Gut Microbiota as Important Mediator Between Diet and DNA Methylation and Histone Modifications in the Host. Nutrients. 2020 Feb 25;12(3):597. doi: 10.3390/nu12030597.
2 Arachidonic and oleic acid exert distinct effects on the DNA methylome. Epigenetics. 2016 May 3;11(5):321-34. doi: 10.1080/15592294.2016.1161873. Epub 2016 Apr 18.
3 Dietary metabolites derived from gut microbiota: critical modulators of epigenetic changes in mammals. Nutr Rev. 2017 May 1;75(5):374-389. doi: 10.1093/nutrit/nux001.
4 Total Lipopolysaccharide from the Human Gut Microbiome Silences Toll-Like Receptor Signaling mSystems. 2017 Nov 14;2(6):e00046-17. doi: 10.1128/mSystems.00046-17. eCollection 2017 Nov-Dec.
5 Valerian and valeric acid inhibit growth of breast cancer cells possibly by mediating epigenetic modifications. Sci Rep. 2021 Jan 28;11(1):2519. doi: 10.1038/s41598-021-81620-x.

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