You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:36 UTC
HMDB IDHMDB00951
Secondary Accession NumbersNone
Metabolite Identification
Common NameTaurochenodesoxycholic acid
DescriptionTaurochenodesoxycholic acid is a bile acid formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. 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 ).
Structure
Thumb
Synonyms
ValueSource
ChenodeoxycholoyltaurineChEBI
Taurine chenodeoxycholateChEBI
TaurochenodeoxycholateChEBI
12-DeoxycholyltaurineHMDB
12-DesoxycholyltaurineHMDB
3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amideHMDB
ChenodeoxycholyltaurineHMDB
ChenyltaurineHMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-taurineHMDB
Taurochenodeoxycholic acidHMDB
TaurochenodesoxycholateHMDB
Chemical FormulaC26H45NO6S
Average Molecular Weight499.704
Monoisotopic Molecular Weight499.296758867
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
Traditional Nametaurochenodeoxycholate
CAS Registry Number516-35-8
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1
InChI KeyInChIKey=BHTRKEVKTKCXOH-BJLOMENOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTaurinated bile acids and derivatives
Alternative Parents
Substituents
  • Taurinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
  • Microbial
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0075 mg/mLALOGPS
logP1.38ALOGPS
logP0.81ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-0.99ChemAxon
pKa (Strongest Basic)0.18ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.68 m3·mol-1ChemAxon
Polarizability56.64 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Bile
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BileDetected and Quantified>0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.30 +/- 0.08 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected and Quantified6.03 +/- 5.00 nmol/g of fecesNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.00065 +/- 0.0019 umol/mmol creatinineChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Recurrent Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Recurrent Clostridium difficile infection
details
UrineDetected and Quantified0.013 +/- 0.021 umol/mmol creatinineAdult (>18 years old)BothBiliary atresia details
Associated Disorders and Diseases
Disease References
Biliary atresia
  1. Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [3944741 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022335
KNApSAcK IDNot Available
Chemspider ID343282
KEGG Compound IDC05465
BioCyc IDCHENODEOXYCHOLOYLTAURINE
BiGG ID45864
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00951
Metagene LinkHMDB00951
METLIN ID5897
PubChem Compound387316
PDB IDTUD
ChEBI ID16525
References
Synthesis ReferenceKarbach Ia I; Rybak P G Synthesis of conjugated bile acids. Ukrainskii biokhimicheskii zhurnal (1979), 51(1), 76-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [659989 ]
  2. Makino I, Shinozaki K, Nakagawa S, Mashimo K: Measurement of sulfated and nonsulfated bile acids in human serum and urine. J Lipid Res. 1974 Mar;15(2):132-8. [4832755 ]
  3. Pouwels MJ, Tack CJ, Span PN, Olthaar AJ, Sweep CG, Huvers FC, Lutterman JA, Hermus AR: Role of hexosamines in insulin resistance and nutrient sensing in human adipose and muscle tissue. J Clin Endocrinol Metab. 2004 Oct;89(10):5132-7. [15472217 ]
  4. Ijare OB, Somashekar BS, Jadegoud Y, Nagana Gowda GA: 1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media. Lipids. 2005 Oct;40(10):1031-41. [16382575 ]
  5. Schwenk M, Hofmann AF, Carlson GL, Carter JA, Coulston F, Greim H: Bile acid conjugation in the chimpanzee: effective sulfation of lithocholic acid. Arch Toxicol. 1978 Apr 27;40(2):109-18. [580732 ]
  6. Bolhuis PA, Sinaasappel M: Bile acid clearance and biocompatibility of XAD-4 haemoperfusion. Int J Artif Organs. 1978 May;1(3):135-41. [689756 ]
  7. Roda A, Pellicciari R, Polimeni C, Cerre C, Forti GC, Sadeghpour B, Sapigni E, Gioacchini AM, Natalini B: Metabolism, pharmacokinetics, and activity of a new 6-fluoro analogue of ursodeoxycholic acid in rats and hamsters. Gastroenterology. 1995 Apr;108(4):1204-14. [7698590 ]
  8. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [11316487 ]
  9. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [16037564 ]
  10. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [12576301 ]
  11. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [11907135 ]

Enzymes

General function:
Involved in thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
BAAT
Uniprot ID:
Q14032
Molecular weight:
46298.865
Reactions
Chenodeoxycholoyl-CoA + Taurine → Taurochenodesoxycholic acid + Coenzyme Adetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Reactions
Taurochenodesoxycholic acid + NADPH + Oxygen → Taurohyocholate + NADP + Waterdetails