General Information of MET (ID: META00132)
Name Taurocholic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
3a,7a,12a-Trihydroxy-5b-cholanate 24-taurine; 3a,7a,12a-Trihydroxy-5b-cholanic acid 24-taurine; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid 24-taurine; Cholaate; Cholaic acid; Cholate taurine conjugate; Cholic acid taurine conjugate; Cholic acid taurine conjugic acid; Choloyl-taurine; Cholyltaurine; N-Choloyltaurine; Taurine cholate; Taurocholate; Taurocholic acid, (5 alpha)-isomer; Taurocholic acid, (7 beta)-isomer
Source Endogenous;Yeast Metabolite;Sterol lipids;Food;Drug;Food additives;TCM Ingredients;Microbial
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
6675
HMDB ID
HMDB0000036
Formula
C26H45NO7S
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
C05122
DrugBank ID
DB04348
ChEBI ID
28865
FooDB ID
FDB012335
ChemSpider ID
6423
METLIN ID
5104
Physicochemical Properties Molecular Weight 515.7 Topological Polar Surface Area 153
XlogP 2.2 Complexity 891
Heavy Atom Count 35 Rotatable Bond Count 7
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 7
Function
Taurocholic acid is a bile acid and is the product of the conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. 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. Taurocholic acid, as with all bile acids, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic (a bile purging agent). Hydrolysis of taurocholic acid yields taurine, a nonessential amino acid. Taurocholic acid is one of the main components of urinary nonsulfated bile acids in biliary atresia. Raised levels of taurocholate in fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and sudden intra-uterine death.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      ATP-binding cassette transporter (ABCT)
            ATP-binding cassette A8 (ABCA8) 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 Overexpression of ABCA8
                      Induced Change Taurocholic acid concentration: decrease (FC = 0.63)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of ABCA8 leads to the decrease of taurocholic acid levels compared with control group.
      Fatty acid transporter (FAT)
            Solute carrier family 27 member 5 (SLC27A5) 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 [2]
                      Introduced Variation Knockdown (shRNA) of Slc27a5
                      Induced Change Taurocholic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockdown of Slc27a5 leads to the decrease of taurocholic acid levels compared with control group.
      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 [3]
                      Introduced Variation Knockout of Ppara
                      Induced Change Taurocholic 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 taurocholic acid levels compared with control group.
      Transferases (EC 2)
            Pyrophosphate geranylgeranyl synthase (GGPS1) 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 [4]
                      Introduced Variation Knockout of Ggps1
                      Induced Change Taurocholic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Metabolic liver disease [ICD-11: 5C90]
                      Details It is reported that knockout of Ggps1 leads to the decrease of taurocholic acid levels compared with control group.
References
1 ATP-Binding Cassette Transporter A Subfamily 8 Is a Sinusoidal Efflux Transporter for Cholesterol and Taurocholate in Mouse and Human Liver. Mol Pharm. 2018 Feb 5;15(2):343-355.
2 Attenuation of Slc27a5 gene expression followed by LC-MS measurement of bile acid reconjugation using metabolomics and a stable isotope tracer strategy. J Proteome Res. 2011 Oct 7;10(10):4683-91.
3 Targeted Metabolomics Reveals a Protective Role for Basal PPAR in Cholestasis Induced by -Naphthylisothiocyanate. J Proteome Res. 2018 Apr 6;17(4):1500-1508.
4 Conditional loss of geranylgeranyl diphosphate synthase alleviates acute obstructive cholestatic liver injury by regulating hepatic bile acid metabolism. FEBS J. 2020 Aug;287(15):3328-3345.

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