Tauroursodeoxycholic acid (CHEM022766)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:51:22 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022766
Identification
Common NameTauroursodeoxycholic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
TauroursodeoxycholateGenerator
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonateHMDB
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonic acidHMDB
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonateHMDB
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonic acidHMDB
3a,7b-Dihydroxy-5b-cholanoyltaurineHMDB
N-(3-alpha,7-beta-Dihydroxy-5-beta-cholan-24-oyl)-taurineHMDB
TUDCAHMDB
UR 906HMDB
UrsodeoxycholyltaurineHMDB
Tauroursodeoxycholic acid, monosodium salt, (3alpha,5beta,7alpha)-isomerHMDB
Tauroursodeoxycholic acid, (3alpha,5alpha,7alpha)-isomerHMDB
Tauroursodeoxycholic acid, monosodium salt, (3alpha,7alpha)-isomerHMDB
(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulfoethyl)pentanimidateHMDB
(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidateHMDB
(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidic acidHMDB
Chemical FormulaC26H45NO6S
Average Molecular Mass499.704 g/mol
Monoisotopic Mass499.297 g/mol
CAS Registry Number14605-22-2
IUPAC Name2-[(4R)-4-[(1S,2S,5R,9S,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 Name2-[(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid
SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCCS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)CC2C[C@H](O)CC[C@]12C
InChI IdentifierInChI=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 KeyBHTRKEVKTKCXOH-VSHSPWMTSA-N
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
Substituents
  • Taurinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Alkanesulfonic acid
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0075 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.68 m³·mol⁻¹ChemAxon
Polarizability56.31 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-0212900000-14bc097af3f7499753d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4214259000-4a72734ef61b01c2f556Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0801920000-ecfc97935416325b3ca5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2901100000-9a3cf7f2963c041be363Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8904100000-98cfa2606dbba4ef47a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-2001900000-4adf0e40de3812e8d0baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6404900000-4d05b6f0352aebf4228dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9102000000-63892e6e06f1123f8bfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-31f17d1d48b7afdf3baeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-f4f03ef481870394f9e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100300000-654e1207ef97c7662b6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gx0-0000940000-9827b7f4a5b2f54a7bd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0nmi-4639730000-a8491d87ed7e9a353ee5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7x-3893000000-cc5d0b26da084a4d3a35Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000874
FooDB IDFDB022294
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5835
PDB IDNot Available
Wikipedia LinkTauroursodeoxycholic acid
Chemspider ID25949321
ChEBI IDNot Available
PubChem Compound ID12443252
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhuo, Chao; Feng, Wei; Wu, Da-jun; Xiong, Zhi-gang. Synthesis of tauroursodeoxycholic acid. Hecheng Huaxue (2002), 10(5), 444-446.
2. Rolo AP, Palmeira CM, Holy JM, Wallace KB: Role of mitochondrial dysfunction in combined bile acid-induced cytotoxicity: the switch between apoptosis and necrosis. Toxicol Sci. 2004 May;79(1):196-204. Epub 2004 Feb 19.
3. Tessier E, Neirinck L, Zhu Z: High-performance liquid chromatographic mass spectrometric method for the determination of ursodeoxycholic acid and its glycine and taurine conjugates in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Dec 25;798(2):295-302.
4. Yamaguchi Y, Itami S, Nishida K, Ando Y, Okamoto S, Hosokawa K, Yoshikawa K: Taurin-conjugated ursodeoxycholic acid has a reversible inhibitory effect on human keratinocyte growth. J Dermatol Sci. 1998 Sep;18(1):35-42.
5. Shekels LL, Beste JE, Ho SB: Tauroursodeoxycholic acid protects in vitro models of human colonic cancer cells from cytotoxic effects of hydrophobic bile acids. J Lab Clin Med. 1996 Jan;127(1):57-66.
6. Lee DK, Park SY, Baik SK, Kwon SO, Chung JM, Oh ES, Kim HS: [Deoxycholic acid-induced signal transduction in HT-29 cells: role of NF-kappa B and interleukin-8]. Korean J Gastroenterol. 2004 Mar;43(3):176-85.
7. Cai W, Khaoustov VI, Xie Q, Pan T, Le W, Yoffe B: Interferon-alpha-induced modulation of glucocorticoid and serotonin receptors as a mechanism of depression. J Hepatol. 2005 Jun;42(6):880-7. Epub 2005 Apr 7.
8. Loria P, Bozzoli M, Concari M, Guicciardi ME, Carubbi F, Bertolotti M, Piani D, Nistri A, Angelico M, Romani M, Carulli N: Effect of taurohyodeoxycholic acid on biliary lipid secretion in humans. Hepatology. 1997 Jun;25(6):1306-14.
9. Henzel K, Thorborg C, Hofmann M, Zimmer G, Leuschner U: Toxicity of ethanol and acetaldehyde in hepatocytes treated with ursodeoxycholic or tauroursodeoxycholic acid. Biochim Biophys Acta. 2004 Feb 2;1644(1):37-45.
10. 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.
11. 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.
12. 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.
13. 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.