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Human Metabolome Database Version 2.5

 

Showing metabocard for Lithocholyltaurine (HMDB00722)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:12
Accession Number HMDB00722
Secondary Accession Numbers Not Available
Common Name Lithocholyltaurine
Description Lithocholyltaurine 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)
Synonyms
  1. 2-[(3alpha-hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid
  2. 2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonate
  3. 2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonic acid
  4. 3a-Hydroxy-5b-cholanoyltaurine
  5. 3a-Hydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide
  6. Cholane ethanesulfonic acid deriv.
  7. Lithocholic acid taurine conjugate
  8. Lithocholic acid taurine conjugic acid
  9. N-(3a-hydroxy-5b-cholan-24-oyl)-Taurine
  10. taurolithocholate
  11. Taurolithocholic acid
Chemical IUPAC Name 2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
Chemical Formula C26H45NO5S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Bile Acids
Sub Class
  • Sulfated steroids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • secondary carboxylic acid amide
  • sulfonic acid
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 483.704
Monoisotopic Molecular Weight 483.301849
Isomeric SMILES C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
Canonical SMILES CC(CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID C02592 Link Image
BioCyc ID TAUROLITHOCHOLATE-SULFATE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00722 Link Image
Metagene Link HMDB00722 Link Image
METLIN ID 5690 Link Image
PubChem Compound 439763 Link Image
PubChem Substance 10298455 Link Image
ChEBI ID 36259 Link Image
CAS Registry Number 516-90-5
InChI Identifier InChI=1/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
Synthesis Reference Zhang, 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.
Melting Point (Experimental) 212-213 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.77e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Liquid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 2.10 [Predicted by ALOGPS]; 5.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Bile
  • Blood
Tissue Location
Tissue References
Gall Bladder —
Intestine —
Concentrations (Normal)
Biofluid Bile
Value 370.0 (350.0-380.0) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Blood
Value 0.614 +/- 0.013 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • Burkard I, von Eckardstein A, Rentsch KM: Differentiated quantification of human bile acids in serum by high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Nov 5;826(1-2):147-59. Epub 2005 Sep 22. [PubMed Link Image]
Biofluid Blood
Value 1.810 +/- 0.002 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Drug-induced cholestasis (under treatment)
References
  • Burkard I, von Eckardstein A, Rentsch KM: Differentiated quantification of human bile acids in serum by high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Nov 5;826(1-2):147-59. Epub 2005 Sep 22. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
General References
  1. 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 Link Image]
  2. 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 Link Image]