1.02011-09-21 00:10:02 UTC2015-07-21 06:57:03 UTCFDB022203LithocholyltaurineLithocholyltaurine 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) [HMDB]2-[(3alpha-hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonate2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonic acid3a-Hydroxy-5b-cholanoyltaurine3a-Hydroxy-N-(2-sulfoethyl)-5b-cholan-24-amideCholane ethanesulfonic acid deriv.Lithocholic acid taurine conjugateLithocholic acid taurine conjugic acidN-(3a-hydroxy-5b-cholan-24-oyl)-TaurinetaurolithocholateTaurolithocholic acidC26H45NO5S483.704483.3018442452-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid516-90-5C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12CInChI=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/s1QBYUNVOYXHFVKC-LVMSMGIASA-N 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.Taurinated bile acids and derivativesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesBile acids, alcohols and derivativesAliphatic homopolycyclic compounds3-alpha-hydroxysteroidsAlkanesulfonic acidsCarbonyl compoundsCyclic alcohols and derivativesHydrocarbon derivativesMonohydroxy bile acids, alcohols and derivativesN-acyl aminesOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOrganosulfonic acidsSecondary alcoholsSecondary carboxylic acid amidesSulfonyls3-alpha-hydroxysteroid3-hydroxysteroidAlcoholAliphatic homopolycyclic compoundAlkanesulfonic acidCarbonyl groupCarboxamide groupCarboxylic acid derivativeCyclic alcoholFatty acylFatty amideHydrocarbon derivativeHydroxy bile acid, alcohol, or derivativesHydroxysteroidMonohydroxy bile acid, alcohol, or derivativesN-acyl-amineOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic sulfonic acid or derivativesOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOrganosulfonic acidOrganosulfonic acid or derivativesOrganosulfur compoundSecondary alcoholSecondary carboxylic acid amideSulfonylTaurinated bile acidLiquidlogp2.10logs-6.24solubility2.77e-04 g/llogp2.48pka_strongest_acidic-0.63pka_strongest_basic-1.1iupac2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acidaverage_mass483.704mono_mass483.301844245smilesC[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12CformulaC26H45NO5SinchiInChI=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/s1inchikeyQBYUNVOYXHFVKC-LVMSMGIASA-Npolar_surface_area103.7refractivity129.09polarizability55.73rotatable_bond_count7acceptor_count5donor_count3physiological_charge-1formal_charge0Bile Acid BiosynthesisSMP00035map00120Specdb::CMs17054Specdb::CMs37722Specdb::MsMs82389Specdb::MsMs82390Specdb::MsMs82391Specdb::MsMs143733Specdb::MsMs143734Specdb::MsMs143735HMDB0072236259#<Reference:0x0000555670ba77c0>#<Reference:0x0000555670ba42f0>#<Reference:0x0000555670b9ec38>#<Reference:0x0000555670b9d3b0>#<Reference:0x0000555670b9b7e0>#<Reference:0x0000555670b9aa20>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Bile salt sulfotransferaseQ06520SULT2A1