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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 17:43:45 UTC
HMDB IDHMDB0000874
Secondary Accession Numbers
  • HMDB00874
Metabolite Identification
Common NameTauroursodeoxycholic acid
DescriptionTauroursodeoxycholic acid is a bile acid also known as TUDCA formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. TUDCA is able to prevent apoptosis and protect mitochondria from cellular elements that would otherwise interfere with energy production. One of these elements is a protein called Bax. TUDCA plays an important role in preventing Bax from being transported to the mitochondria. 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 ).
Structure
Data?1582752161
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 Weight499.704
Monoisotopic Molecular Weight499.296758867
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
CAS Registry Number14605-22-2
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 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 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
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+219.02632859911
AllCCS[M-H]-209.99432859911
DeepCCS[M-2H]-252.22330932474
DeepCCS[M+Na]+227.35130932474
AllCCS[M+H]+219.032859911
AllCCS[M+H-H2O]+217.632859911
AllCCS[M+NH4]+220.332859911
AllCCS[M+Na]+220.732859911
AllCCS[M-H]-210.032859911
AllCCS[M+Na-2H]-212.532859911
AllCCS[M+HCOO]-215.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tauroursodeoxycholic acid[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@]12C4887.6Standard polar33892256
Tauroursodeoxycholic acid[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@]12C3975.7Standard non polar33892256
Tauroursodeoxycholic acid[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@]12C4567.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tauroursodeoxycholic acid,1TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4179.8Semi standard non polar33892256
Tauroursodeoxycholic acid,1TMS,isomer #2C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4297.9Semi standard non polar33892256
Tauroursodeoxycholic acid,1TMS,isomer #3C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4348.3Semi standard non polar33892256
Tauroursodeoxycholic acid,1TMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4270.8Semi standard non polar33892256
Tauroursodeoxycholic acid,2TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4132.9Semi standard non polar33892256
Tauroursodeoxycholic acid,2TMS,isomer #2C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4209.7Semi standard non polar33892256
Tauroursodeoxycholic acid,2TMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4104.5Semi standard non polar33892256
Tauroursodeoxycholic acid,2TMS,isomer #4C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4353.5Semi standard non polar33892256
Tauroursodeoxycholic acid,2TMS,isomer #5C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4271.9Semi standard non polar33892256
Tauroursodeoxycholic acid,2TMS,isomer #6C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4339.3Semi standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4167.4Semi standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4435.2Standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4852.2Standard polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4052.2Semi standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4504.2Standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4917.0Standard polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4151.1Semi standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4542.1Standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4888.9Standard polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4283.6Semi standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4519.8Standard non polar33892256
Tauroursodeoxycholic acid,3TMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4876.7Standard polar33892256
Tauroursodeoxycholic acid,4TMS,isomer #1C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4124.8Semi standard non polar33892256
Tauroursodeoxycholic acid,4TMS,isomer #1C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4645.0Standard non polar33892256
Tauroursodeoxycholic acid,4TMS,isomer #1C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4678.3Standard polar33892256
Tauroursodeoxycholic acid,1TBDMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4371.3Semi standard non polar33892256
Tauroursodeoxycholic acid,1TBDMS,isomer #2C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4497.3Semi standard non polar33892256
Tauroursodeoxycholic acid,1TBDMS,isomer #3C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4532.5Semi standard non polar33892256
Tauroursodeoxycholic acid,1TBDMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4527.9Semi standard non polar33892256
Tauroursodeoxycholic acid,2TBDMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4513.4Semi standard non polar33892256
Tauroursodeoxycholic acid,2TBDMS,isomer #2C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4582.2Semi standard non polar33892256
Tauroursodeoxycholic acid,2TBDMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4554.0Semi standard non polar33892256
Tauroursodeoxycholic acid,2TBDMS,isomer #4C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4758.0Semi standard non polar33892256
Tauroursodeoxycholic acid,2TBDMS,isomer #5C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4715.8Semi standard non polar33892256
Tauroursodeoxycholic acid,2TBDMS,isomer #6C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4791.8Semi standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4742.0Semi standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C5214.2Standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4939.8Standard polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4703.8Semi standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C5223.0Standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C5010.2Standard polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4780.7Semi standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C5325.9Standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4988.3Standard polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4932.6Semi standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C5296.9Standard non polar33892256
Tauroursodeoxycholic acid,3TBDMS,isomer #4C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4968.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-0212900000-14bc097af3f7499753d72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4214259000-4a72734ef61b01c2f5562017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tauroursodeoxycholic acid GC-MS (TBDMS_2_6) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 10V, Positive-QTOFsplash10-00e9-0801920000-ecfc97935416325b3ca52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 20V, Positive-QTOFsplash10-00di-2901100000-9a3cf7f2963c041be3632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 40V, Positive-QTOFsplash10-006x-8904100000-98cfa2606dbba4ef47a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 10V, Negative-QTOFsplash10-000t-2001900000-4adf0e40de3812e8d0ba2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 20V, Negative-QTOFsplash10-001i-6404900000-4d05b6f0352aebf4228d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 40V, Negative-QTOFsplash10-001l-9102000000-63892e6e06f1123f8bfc2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 10V, Negative-QTOFsplash10-0002-0000900000-31f17d1d48b7afdf3bae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 20V, Negative-QTOFsplash10-0002-0000900000-f4f03ef481870394f9e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 40V, Negative-QTOFsplash10-001i-9100300000-654e1207ef97c7662b6e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 10V, Positive-QTOFsplash10-0gx0-0000940000-9827b7f4a5b2f54a7bd42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 20V, Positive-QTOFsplash10-0nmi-4639730000-a8491d87ed7e9a353ee52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tauroursodeoxycholic acid 40V, Positive-QTOFsplash10-0f7x-3893000000-cc5d0b26da084a4d3a352021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.1-4.0) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.30 +/- 0.37 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Pancreatic ductal adenocarcinoma
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation 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 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022294
KNApSAcK IDNot Available
Chemspider ID25949321
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTauroursodeoxycholic acid
METLIN ID5835
PubChem Compound12443252
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceZhuo, Chao; Feng, Wei; Wu, Da-jun; Xiong, Zhi-gang. Synthesis of tauroursodeoxycholic acid. Hecheng Huaxue (2002), 10(5), 444-446.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:14976352 ]
  2. 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. [PubMed:14643509 ]
  3. 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. [PubMed:9747660 ]
  4. 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. [PubMed:8592097 ]
  5. 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. [PubMed:15034288 ]
  6. 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. [PubMed:15885359 ]
  7. 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. [PubMed:9185744 ]
  8. 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. [PubMed:14741743 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]