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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:05 UTC
Secondary Accession Numbers
  • HMDB00951
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 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 (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Taurochenodesoxycholic acid has been found to be a microbial metabolite.
Taurine chenodeoxycholateChEBI
Taurochenodeoxycholic acidKegg
Taurine chenodeoxycholic acidGenerator
Acid, taurochenodeoxycholicHMDB
Chenodeoxycholate, taurineHMDB
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[^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
Traditional Name2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number516-35-8
InChI Identifier
Chemical Taxonomy
Description 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
  • Taurinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Alkanesulfonic acid
  • Cyclic alcohol
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physiological effect

Health effect:


Route of exposure:

Biological location:



Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
Water Solubility0.0075 g/LALOGPS
pKa (Strongest Acidic)-0.8ChemAxon
pKa (Strongest Basic)-0.32ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.68 m³·mol⁻¹ChemAxon
Polarizability56.66 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available205.394
DarkChem[M+H]+PredictedNot Available31661259
DarkChem[M-H]-PredictedNot Available31661259
AllCCS[M+H]+PredictedNot Available218.69832859911
AllCCS[M-H]-PredictedNot Available209.89232859911

Retention Indices


Not Available


Taurochenodesoxycholic acid,1TMS,#14160.526
Taurochenodesoxycholic acid,1TMS,#24274.3057
Taurochenodesoxycholic acid,1TMS,#34333.293
Taurochenodesoxycholic acid,1TMS,#44263.8022
Taurochenodesoxycholic acid,2TMS,#14115.8843
Taurochenodesoxycholic acid,2TMS,#24193.1006
Taurochenodesoxycholic acid,2TMS,#34085.6904
Taurochenodesoxycholic acid,2TMS,#44329.008
Taurochenodesoxycholic acid,2TMS,#54246.244
Taurochenodesoxycholic acid,2TMS,#64329.3784
Taurochenodesoxycholic acid,1TBDMS,#14355.7036
Taurochenodesoxycholic acid,1TBDMS,#24473.279
Taurochenodesoxycholic acid,1TBDMS,#34519.665
Taurochenodesoxycholic acid,1TBDMS,#44520.9414
Taurochenodesoxycholic acid,2TBDMS,#14506.3105
Taurochenodesoxycholic acid,2TBDMS,#24578.1357
Taurochenodesoxycholic acid,2TBDMS,#34544.1943
Taurochenodesoxycholic acid,2TBDMS,#44738.6016
Taurochenodesoxycholic acid,2TBDMS,#54695.306
Taurochenodesoxycholic acid,2TBDMS,#64779.086


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-0212900000-197acffecf402e5986442017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4214329000-11c176071503161e2cd42017-10-06View Spectrum


Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-02ar-0006900000-53366e607f8bd2e507832017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0og0-1595100000-2488fbc0ad2dab2256842021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0000920000-d308c77003ce029da3222021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-4f77a6fb2b33e4e1a35f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-671f53e46ce019da43dc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0og0-1595100000-6670e8e89de5e9a0c3a12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0000920000-0b63233ca30c95bee5952021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-54b7fff092e1f9db6a202021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-0000900000-f978cbaedb898eee18432021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0801920000-ecfc97935416325b3ca52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2901100000-9a3cf7f2963c041be3632016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8904100000-98cfa2606dbba4ef47a02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-2001900000-4adf0e40de3812e8d0ba2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6404900000-4d05b6f0352aebf4228d2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9102000000-63892e6e06f1123f8bfc2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0000970000-8561365963466c5db0932021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvi-3509710000-451e758e0b96f9fa8ee72021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l5-9463000000-16d35ecb5101cbd28ea92021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-31f17d1d48b7afdf3bae2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-a426f175803c68cb83132021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-7400900000-5a469259d1091a8583472021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Bile
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Normal Concentrations
BileDetected and Quantified>0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.30 +/- 0.08 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.3(0.1-0.3) uMInfant (0-1 year old)Both
FecesDetected and Quantified6.03 +/- 5.00 nmol/g dry fecesNot SpecifiedNot Specified
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00065 +/- 0.0019 umol/mmol creatinineChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.4(0.3-1.2) uMInfant (0-1 year old)Both
Severe acute malnutrition
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Recurrent Clostridium difficile infection
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Recurrent Clostridium difficile infection
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothClostridium difficile infection details
UrineDetected and Quantified0.013 +/- 0.021 umol/mmol creatinineAdult (>18 years old)BothBiliary atresia details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
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. [PubMed:3944741 ]
Associated OMIM IDs
DrugBank IDDB08833
Phenol Explorer Compound IDNot Available
FooDB IDFDB022335
KNApSAcK IDNot Available
Chemspider ID343282
KEGG Compound IDC05465
BiGG ID45864
Wikipedia LinkNot Available
PubChem Compound387316
PDB IDNot Available
ChEBI ID16525
Food Biomarker OntologyNot Available
MarkerDB IDNot Available
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. [PubMed:659989 ]
  2. 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. [PubMed:16382575 ]
  3. 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. [PubMed:580732 ]
  4. 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. [PubMed:15472217 ]
  5. 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. [PubMed:4832755 ]
  6. Bolhuis PA, Sinaasappel M: Bile acid clearance and biocompatibility of XAD-4 haemoperfusion. Int J Artif Organs. 1978 May;1(3):135-41. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:11907135 ]
  12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]


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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
Taurochenodesoxycholic acid + NADPH + Oxygen → Taurohyocholate + NADP + Waterdetails