General Information of MET (ID: META00338)
Name Tauroursodeoxycholic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonate; 2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonic acid; 2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonate; 2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonic acid; 3a,7b-Dihydroxy-5b-cholanoyltaurine; N-(3-alpha,7-beta-Dihydroxy-5-beta-cholan-24-oyl)-taurine; TUDCA; Tauroursodeoxycholate; Tauroursodeoxycholic acid, (3alpha,5alpha,7alpha)-isomer; Tauroursodeoxycholic acid, monosodium salt, (3alpha,5beta,7alpha)-isomer; UR 906; Ursodeoxycholyltaurine
Source Endogenous;Food
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
12443252
HMDB ID
HMDB0000874
Formula
C26H45NO6S
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
FooDB ID
FDB022294
ChemSpider ID
25949321
METLIN ID
5835
Physicochemical Properties Molecular Weight 499.7 Topological Polar Surface Area 132
XlogP 3.6 Complexity 858
Heavy Atom Count 34 Rotatable Bond Count 7
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Function
Tauroursodeoxycholic acid is a bile acid also known as TUDCA formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. TUDCA is able to prevent apoptosis and protect mitochondria from cellular elements that would otherwise interfere with energy production. One of these elements is a protein called Bax. TUDCA plays an important role in preventing Bax from being transported to the mitochondria. 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 Tauroursodeoxycholic 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 tauroursodeoxycholic 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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