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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:08 UTC
NP-MRD IDNP0000461
Secondary Accession NumbersNone
Natural Product Identification
Common NameTaurocholic acid
DescriptionTaurocholic 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 (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 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 (PMID: 3944741 , 11256973 ).
Structure
Thumb
Synonyms
ValueSource
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid 24-taurineChEBI
Cholic acid taurine conjugateChEBI
Choloyl-taurineChEBI
CholyltaurineChEBI
N-CholoyltaurineChEBI
TaurocholateChEBI
3a,7a,12a-Trihydroxy-5b-cholanate 24-taurineGenerator
3a,7a,12a-Trihydroxy-5b-cholanic acid 24-taurineGenerator
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate 24-taurineGenerator
3Α,7α,12α-trihydroxy-5β-cholanate 24-taurineGenerator
3Α,7α,12α-trihydroxy-5β-cholanic acid 24-taurineGenerator
Cholate taurine conjugateGenerator
Cholic acid taurine conjugic acidGenerator
Cholaic acidHMDB
CholaateHMDB
Taurine cholateHMDB
Taurocholic acid, (7 beta)-isomerHMDB
Taurocholic acid, (5 alpha)-isomerHMDB
Chemical FormulaC26H45NO7S
Average Mass515.7030 Da
Monoisotopic Mass515.29167 Da
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{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,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number81-24-3
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])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
InChI Identifier
InChI=1S/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-/m1/s1
InChI KeyWBWWGRHZICKQGZ-HZAMXZRMSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Polygala amarellaKNApSAcK Database
Polygala tenuifolia Willd.KNApSAcK Database
Selenarctos thibetanusLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Synechococcus elongatusLOTUS Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Secondary alcohol
  • Carboximidic acid
  • Polyol
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility555.4 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.247 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP0.79ALOGPS
logP-0.24ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)-0.88ChemAxon
pKa (Strongest Basic)-0.053ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.16 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity132.19 m³·mol⁻¹ChemAxon
Polarizability57.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0000036
DrugBank IDDB04348
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012335
KNApSAcK IDC00037897
Chemspider ID6423
KEGG Compound IDC05122
BioCyc IDNot Available
BiGG ID45150
Wikipedia LinkTaurocholic_acid
METLIN ID5104
PubChem Compound6675
PDB IDNot Available
ChEBI ID28865
Good Scents IDrw1611841
References
General References
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  2. Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [PubMed:12883481 ]
  3. Hoekman MF, Rientjes JM, Twisk J, Planta RJ, Princen HM, Mager WH: Transcriptional regulation of the gene encoding cholesterol 7 alpha-hydroxylase in the rat. Gene. 1993 Aug 25;130(2):217-23. [PubMed:8359688 ]
  4. Sandker GW, Weert B, Olinga P, Wolters H, Slooff MJ, Meijer DK, Groothuis GM: Characterization of transport in isolated human hepatocytes. A study with the bile acid taurocholic acid, the uncharged ouabain and the organic cations vecuronium and rocuronium. Biochem Pharmacol. 1994 Jun 15;47(12):2193-200. [PubMed:7913319 ]
  5. Kullak-Ublick GA, Glasa J, Boker C, Oswald M, Grutzner U, Hagenbuch B, Stieger B, Meier PJ, Beuers U, Kramer W, Wess G, Paumgartner G: Chlorambucil-taurocholate is transported by bile acid carriers expressed in human hepatocellular carcinomas. Gastroenterology. 1997 Oct;113(4):1295-305. [PubMed:9322525 ]
  6. Claudel T, Inoue Y, Barbier O, Duran-Sandoval D, Kosykh V, Fruchart J, Fruchart JC, Gonzalez FJ, Staels B: Farnesoid X receptor agonists suppress hepatic apolipoprotein CIII expression. Gastroenterology. 2003 Aug;125(2):544-55. [PubMed:12891557 ]
  7. Rizzo G, Renga B, Mencarelli A, Pellicciari R, Fiorucci S: Role of FXR in regulating bile acid homeostasis and relevance for human diseases. Curr Drug Targets Immune Endocr Metabol Disord. 2005 Sep;5(3):289-303. [PubMed:16178789 ]
  8. Duan RD, Cheng Y, Tauschel HD, Nilsson A: Effects of ursodeoxycholate and other bile salts on levels of rat intestinal alkaline sphingomyelinase: a potential implication in tumorigenesis. Dig Dis Sci. 1998 Jan;43(1):26-32. [PubMed:9508530 ]
  9. Akao T: Influence of various bile acids on the metabolism of glycyrrhizin and glycyrrhetic acid by Ruminococcus sp. PO1-3 of human intestinal bacteria. Biol Pharm Bull. 1999 Aug;22(8):787-93. [PubMed:10480314 ]
  10. Jigorel E, Le Vee M, Boursier-Neyret C, Bertrand M, Fardel O: Functional expression of sinusoidal drug transporters in primary human and rat hepatocytes. Drug Metab Dispos. 2005 Oct;33(10):1418-22. Epub 2005 Jul 13. [PubMed:16014767 ]
  11. Zahner D, Eckhardt U, Petzinger E: Transport of taurocholate by mutants of negatively charged amino acids, cysteines, and threonines of the rat liver sodium-dependent taurocholate cotransporting polypeptide Ntcp. Eur J Biochem. 2003 Mar;270(6):1117-27. [PubMed:12631271 ]
  12. Wang LF, Luo H, Miyoshi M, Imoto T, Hiji Y, Sasaki T: Inhibitory effect of gymnemic acid on intestinal absorption of oleic acid in rats. Can J Physiol Pharmacol. 1998 Oct-Nov;76(10-11):1017-23. [PubMed:10100884 ]
  13. Yamamoto Y, Moore R, Hess HA, Guo GL, Gonzalez FJ, Korach KS, Maronpot RR, Negishi M: Estrogen receptor alpha mediates 17alpha-ethynylestradiol causing hepatotoxicity. J Biol Chem. 2006 Jun 16;281(24):16625-31. Epub 2006 Apr 10. [PubMed:16606610 ]
  14. Kwekkeboom J, Princen HM, van Voorthuizen EM, Meijer P, Kempen HJ: Comparison of taurocholate accumulation in cultured hepatocytes of pig, rat and man. Biochem Biophys Res Commun. 1989 Jul 31;162(2):619-25. [PubMed:2757635 ]
  15. Claudel T, Sturm E, Duez H, Torra IP, Sirvent A, Kosykh V, Fruchart JC, Dallongeville J, Hum DW, Kuipers F, Staels B: Bile acid-activated nuclear receptor FXR suppresses apolipoprotein A-I transcription via a negative FXR response element. J Clin Invest. 2002 Apr;109(7):961-71. [PubMed:11927623 ]
  16. Perwaiz S, Tuchweber B, Mignault D, Gilat T, Yousef IM: Determination of bile acids in biological fluids by liquid chromatography-electrospray tandem mass spectrometry. J Lipid Res. 2001 Jan;42(1):114-9. [PubMed:11160372 ]
  17. Johnson RC, Shah SN: Cholesterol ester hydrolase(s) in mammalian brain: is there a myelin-specific cholesterol ester hydrolase? Neurochem Res. 1986 Nov;11(11):1571-82. [PubMed:3683732 ]
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  19. 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 ]
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  21. 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 ]
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  27. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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