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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:05 UTC
HMDB IDHMDB0000722
Secondary Accession Numbers
  • HMDB00722
Metabolite Identification
Common NameLithocholyltaurine
DescriptionLithocholyltaurine is a bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. Lithocholic acid, a hydrophobic secondary bile acid, is well known to cause intrahepatic cholestasis. There have been extensive studies on the mechanisms of lithocholate-induced cholestasis in animals. Lithocholate diminishes both the bile acid-dependent and independent bile flow. In humans, elevated levels of lithocholic acid are found in patients with chronic cholestatic liver disease. Lithocholyltaurine impairs both the bile canalicular contractions and the canalicular bile secretion, possibly by acting directly on the canalicular membranes in lithocholyltaurine-induced cholestasis. Lithocholyltaurine induce acute cholestasis-associated with retrieval of the bile salt export pump. The bile salt export pump (BSEP) of hepatocyte secretes conjugated bile salts across the canalicular membrane in an ATP-dependent manner. Hepatic retention of bile acids may lead to liver injury by hepatocyte apoptosis and eventually deterioration of cholestatic liver diseases. One mechanism of induced apoptosis by lithocholyltaurine is the induction of transcriptional activity of AP-1 (activation protein-1). (PMID: 16981261 , 15763547 , 16332456 , 18164257 ).
Structure
Data?1600215566
Synonyms
ValueSource
TaurolithocholateChEBI
Taurolithocholic acidKegg
Taurine lithocholateHMDB
Acid, taurolithocholicHMDB
Taurolithocholic acid, monosodium saltHMDB
Lithocholate, taurineHMDB
3alpha-Hydroxy-5beta-cholanoyltaurineHMDB
3alpha-Hydroxy-N-(2-sulfoethyl)-5beta-cholan-24-amideHMDB
3Α-hydroxy-5β-cholanoyltaurineHMDB
3Α-hydroxy-N-(2-sulfoethyl)-5β-cholan-24-amideHMDB
Lithocholic acid taurine conjugateHMDB
LithocholyltaurineChEBI
Chemical FormulaC26H45NO5S
Average Molecular Weight483.71
Monoisotopic Molecular Weight483.301844727
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-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,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number516-90-5
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[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/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1
InChI KeyQBYUNVOYXHFVKC-GBURMNQMSA-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
  • Hydroxy bile acid, alcohol, or derivatives
  • Monohydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-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 oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point212 - 213 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00028 g/LALOGPS
logP2.1ALOGPS
logP2.48ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)-0.63ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.09 m³·mol⁻¹ChemAxon
Polarizability55.85 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
DeepCCS[M-2H]-254.21930932474
DeepCCS[M+Na]+228.23430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lithocholyltaurine[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[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)=O4509.9Standard polar33892256
Lithocholyltaurine[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[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)=O3973.6Standard non polar33892256
Lithocholyltaurine[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[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)=O4385.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lithocholyltaurine,1TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4184.8Semi standard non polar33892256
Lithocholyltaurine,1TMS,isomer #2C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4227.4Semi standard non polar33892256
Lithocholyltaurine,1TMS,isomer #3C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4181.5Semi standard non polar33892256
Lithocholyltaurine,2TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4245.0Semi standard non polar33892256
Lithocholyltaurine,2TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4178.9Standard non polar33892256
Lithocholyltaurine,2TMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4915.9Standard polar33892256
Lithocholyltaurine,2TMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4180.2Semi standard non polar33892256
Lithocholyltaurine,2TMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4272.3Standard non polar33892256
Lithocholyltaurine,2TMS,isomer #2C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4998.5Standard polar33892256
Lithocholyltaurine,2TMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4237.9Semi standard non polar33892256
Lithocholyltaurine,2TMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4251.6Standard non polar33892256
Lithocholyltaurine,2TMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4866.2Standard polar33892256
Lithocholyltaurine,3TMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4193.9Semi standard non polar33892256
Lithocholyltaurine,3TMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4399.0Standard non polar33892256
Lithocholyltaurine,3TMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4790.6Standard polar33892256
Lithocholyltaurine,1TBDMS,isomer #1C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4405.5Semi standard non polar33892256
Lithocholyltaurine,1TBDMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4411.4Semi standard non polar33892256
Lithocholyltaurine,1TBDMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4416.6Semi standard non polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4659.9Semi standard non polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4723.5Standard non polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4998.6Standard polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4617.9Semi standard non polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4767.1Standard non polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C5094.0Standard polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4679.1Semi standard non polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4782.9Standard non polar33892256
Lithocholyltaurine,2TBDMS,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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4972.7Standard polar33892256
Lithocholyltaurine,3TBDMS,isomer #1C[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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4860.0Semi standard non polar33892256
Lithocholyltaurine,3TBDMS,isomer #1C[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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C5176.9Standard non polar33892256
Lithocholyltaurine,3TBDMS,isomer #1C[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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4897.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholyltaurine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Negative-QTOFsplash10-001i-0000900000-62d017c1c686f7266fb02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Positive-QTOFsplash10-014i-0000900000-370b7bde61cf15901a052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Negative-QTOFsplash10-001i-0000900000-a35b80c6756ffe4a97352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 40V, Negative-QTOFsplash10-001i-0000900000-7d2d59d9367fc3097f6a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Negative-QTOFsplash10-001i-0000900000-cb0b19ca18aeb20850bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 40V, Negative-QTOFsplash10-001i-0000900000-d527b7971f2a108694762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Negative-QTOFsplash10-001i-0000900000-a8f1d5fe4d9c4ae2b9732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Negative-QTOFsplash10-001i-0000900000-b7f7991f18a8750f971a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Negative-QTOFsplash10-001i-0000900000-e08a1b85b998b206ce042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 40V, Negative-QTOFsplash10-001i-0000900000-8f83f6d43ddf7e3ef5182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Positive-QTOFsplash10-014i-0000900000-3c99186da6a80b3848242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Positive-QTOFsplash10-014i-0536900000-3c8a96d3193eee3c45e72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Positive-QTOFsplash10-014i-0000900000-d532dc016f756e1019552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Positive-QTOFsplash10-014i-0000900000-14b55a77ecc8c685282f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Positive-QTOFsplash10-014i-0001900000-4faf258ccbd40728478e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 40V, Positive-QTOFsplash10-00fu-3986000000-6221debd3d96ad748cf02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 40V, Positive-QTOFsplash10-004i-2920000000-8d3c5fefb8cdf48324cc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Positive-QTOFsplash10-014i-0000900000-8e6cbe0112d70a9c75542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Positive-QTOFsplash10-016r-3946800000-c1a033a5e37851135b552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 40V, Positive-QTOFsplash10-0571-5930000000-f06779a0e2a6b59baf2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Positive-QTOFsplash10-014i-0316900000-c834f65be00b11b052562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Positive-QTOFsplash10-014i-0001900000-0dbbc8861a1b2d702ccc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 20V, Positive-QTOFsplash10-014i-1647900000-1959f275d5a4ff01e3602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 40V, Positive-QTOFsplash10-004i-3920000000-79daf69ae12d0ea902f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lithocholyltaurine 10V, Positive-QTOFsplash10-014i-0000900000-07e531c1684fe7ea6a4b2021-09-20HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Bile
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Gall Bladder
  • Intestine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BileDetected and Quantified370.0 (350.0-380.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.614 +/- 0.013 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified1.810 +/- 0.002 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified0.51 +/- 0.40 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 IDFDB022203
KNApSAcK IDNot Available
Chemspider ID388820
KEGG Compound IDC02592
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTaurolithocholic_acid
METLIN ID5690
PubChem Compound439763
PDB IDNot Available
ChEBI ID36259
Food Biomarker OntologyNot Available
VMH IDHC02192
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceZhang, Jie; Griffiths, William J.; Bergman, Tomas; Sjoevall, Jan. Derivatization of bile acids with taurine for analysis by fast atom bombardment mass spectrometry with collision-induced fragmentation. Journal of Lipid Research (1993), 34(11), 1895-900.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
  2. Lee BL, New AL, Ong CN: Comparative analysis of conjugated bile acids in human serum using high-performance liquid chromatography and capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 1997 Dec 19;704(1-2):35-42. [PubMed:9518169 ]
  3. Hayashi H, Takada T, Suzuki H, Onuki R, Hofmann AF, Sugiyama Y: Transport by vesicles of glycine- and taurine-conjugated bile salts and taurolithocholate 3-sulfate: a comparison of human BSEP with rat Bsep. Biochim Biophys Acta. 2005 Dec 30;1738(1-3):54-62. Epub 2005 Nov 15. [PubMed:16332456 ]
  4. Watanabe N, Kagawa T, Kojima S, Takashimizu S, Nagata N, Nishizaki Y, Mine T: Taurolithocholate impairs bile canalicular motility and canalicular bile secretion in isolated rat hepatocyte couplets. World J Gastroenterol. 2006 Sep 7;12(33):5320-5. [PubMed:16981261 ]
  5. Crocenzi FA, Basiglio CL, Perez LM, Portesio MS, Pozzi EJ, Roma MG: Silibinin prevents cholestasis-associated retrieval of the bile salt export pump, Bsep, in isolated rat hepatocyte couplets: possible involvement of cAMP. Biochem Pharmacol. 2005 Apr 1;69(7):1113-20. [PubMed:15763547 ]
  6. Pusl T, Vennegeerts T, Wimmer R, Denk GU, Beuers U, Rust C: Tauroursodeoxycholic acid reduces bile acid-induced apoptosis by modulation of AP-1. Biochem Biophys Res Commun. 2008 Feb 29;367(1):208-12. doi: 10.1016/j.bbrc.2007.12.122. Epub 2007 Dec 27. [PubMed:18164257 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular weight:
33779.57
Reactions
Phosphoadenosine phosphosulfate + Lithocholyltaurine → Adenosine 3',5'-diphosphate + Taurolithocholic acid 3-sulfatedetails