You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-05-13 19:23:41 UTC
HMDB IDHMDB00722
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
2-[(3alpha-Hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acidHMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonateHMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonic acidHMDB
3a-Hydroxy-5b-cholanoyltaurineHMDB
3a-Hydroxy-N-(2-sulfoethyl)-5b-cholan-24-amideHMDB
Cholane ethanesulfonic acid deriv.HMDB
Lithocholic acid taurine conjugateHMDB
Lithocholic acid taurine conjugic acidHMDB
N-(3a-Hydroxy-5b-cholan-24-oyl)-taurineHMDB
TaurolithocholateHMDB
Taurolithocholic acidHMDB
Chemical FormulaC26H45NO5S
Average Molecular Weight483.704
Monoisotopic Molecular Weight483.301844245
IUPAC Name2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
Traditional Name2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number516-90-5
SMILES
C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
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 KeyInChIKey=QBYUNVOYXHFVKC-LVMSMGIASA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monohydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point212 - 213 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000277 mg/mLALOGPS
logP2.1ALOGPS
logP2.19ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)-0.84ChemAxon
pKa (Strongest Basic)0.099ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.09 m3·mol-1ChemAxon
Polarizability55.66 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Bile
  • Blood
  • Feces
Tissue Location
  • Gall Bladder
  • Intestine
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
FecesDetected and Quantified0.51 +/- 0.40 nmol/g of fecesNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022203
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02592
BioCyc IDTAUROLITHOCHOLATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00722
Metagene LinkHMDB00722
METLIN ID5690
PubChem Compound53477716
PDB IDNot Available
ChEBI ID36259
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. [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. [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. [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. [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. [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. [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