Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:37:33 UTC
Update Date2024-04-30 19:31:13 UTC
Metabolite IDMMDBc0000146
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
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
Molecular FormulaC26H45NO5S
Average Mass483.71
Monoisotopic Mass483.301844727
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