General Information of MET (ID: META00254)
Name 3a,6b,7b-Trihydroxy-5b-cholanoic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(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-Oic acid; 3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid; 3,6,7-Trihydroxy-5-cholanoic 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-Oic acid; 3a,6b,7b-Trihydroxy-5b-cholan-24-Oate; 3a,6b,7b-Trihydroxy-5b-cholan-24-Oic acid; 3a,6b,7b-Trihydroxy-5b-cholanate; 3a,6b,7b-Trihydroxy-5b-cholanic acid; 3a,6b,7b-Trihydroxy-5b-cholanoate; 3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oic acid; 5b-Cholanate-3a,6b,7b-triol; 5b-Cholanic acid-3a,6b,7b-triol; 5beta-Cholanic acid-3alpha,6beta,7beta-triol; 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; alpha-Muricholic acid; b-Muricholate; b-Muricholic acid; beta-MCA; beta-Muricholic acid
Source Endogenous;Plant;Metabolite;Sterol lipids;Food;Plant Metabolite
Structure Type   Bile acids, alcohols and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Steroids and steroid derivatives
Bile acids, alcohols and derivatives
PubChem CID
5283853
HMDB ID
HMDB0000415
Formula
C24H40O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C17726
ChEBI ID
81298
FooDB ID
FDB022031
ChemSpider ID
4446941
METLIN ID
5404
Physicochemical Properties Molecular Weight 408.6 Topological Polar Surface Area 98
XlogP 3.9 Complexity 637
Heavy Atom Count 29 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Function
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. 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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Nuclear hormone receptor (NHR)
            PPAR-alpha (PPARA) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Ppara
                      Induced Change 3a,6b,7b-Trihydroxy-5b-cholanoic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Ppara leads to the increase of 3a,6b,7b-trihydroxy-5b-cholanoic acid levels compared with control group.
References
1 Targeted Metabolomics Reveals a Protective Role for Basal PPAR in Cholestasis Induced by -Naphthylisothiocyanate. J Proteome Res. 2018 Apr 6;17(4):1500-1508.

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