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Bovine Metabolome Database



Showing metabocard for Taurocholic acid (BMDB00036)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-26 12:39:06
Accession Number BMDB00036
Common Name Taurocholic acid
Description Taurocholic acid is a bile acid and is the product of 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 bile of mammals. The distinction between different bile acids is minute, depends only on 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) 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 cholerectic (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 the bile acid taurocholate in the fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and in sudden intra-uterine death. (PMID: 3944741, 11256973)
Synonyms
  1. 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-taurine
  2. Cholaic acid
  3. Cholic acid taurine conjugate
  4. Cholyltaurine
  5. N-Choloyltaurine
  6. n-choloyl-Taurine
  7. Taurocholate
Chemical IUPAC Name 2-[4-[(3R,5S,7R,12S)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid
Chemical Formula C26H45NO7S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Bile Acids
Sub Class
  • Taurinated bile acids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; secondary carboxylic acid amide; sulfonic acid
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 515.703
Monoisotopic Molecular Weight 515.291687
Isomeric SMILES CC(CCC(=O)NCCS(O)(=O)=O)C1CCC2C3[C@H](O)C[C@@H]4C[C@H](O)CCC4(C)C3C[C@H](O)C12C
Canonical SMILES CC(CCC(=O)NCCS(O)(=O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
KEGG Compound ID C05122 Link Image
BioCyc ID CPD-3743 Link Image
BiGG ID 45150 Link Image
Wikipedia Link Taurocholate Link Image
METLIN ID 5104 Link Image
PubChem Compound 440567 Link Image
PubChem Substance 7544 Link Image
ChEBI ID 28865 Link Image
CAS Registry Number 81-24-3
InChI Identifier InChI=1/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15?,16-,17+,18?,19?,20?,21+,22-,24?,25?,26?/m0/s1
Synthesis Reference Schersten, Tore; Bjorntorp, Per; Ekdahi, Per H.; Bjorkerud, Soren. Synthesis of taurocholic and glycocholic acids by preparations of human liver. II. An analysis of the stimulating effect of the L fraction. Biochimica et Biophysica Acta, General Subjects (1967), 141(1), 155-63.
Melting Point (Experimental) 125 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 7.17 mg/mL [MEYLAN,WM et al. (1996)]; 0.0771 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 0.79 [Predicted by ALOGPS]; 2.7 [Predicted by PubChem via XLOGP]; 0.01 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1AQL Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
  • Cytoplasm
  • Extracellular
  • peroxisome
Biofluid Location Not Available
Tissue Location
Tissue References
Fibroblasts
Hepatocyte
Intestine
Liver
Myelin
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Bile Acid Biosynthesis
  • Taurine and Hypotaurine Metabolism
HMDB Pathways
Name Bile Acid Biosynthesis
Image Show Link Image
Name Taurine and Hypotaurine Metabolism
Image Show Link Image
KEGG Pathways
Name Bile Acid Biosynthesis
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Name Taurine and Hypotaurine Metabolism
Image Show Link Image
SimCell Pathways
Name Bile Acid Biosynthesis
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Graph
SBML
General References
  1. Wikipedia Link Image