1.0 2011-09-21 00:10:02 UTC 2025-11-19 02:41:06 UTC FDB022203 Lithocholyltaurine 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) [HMDB] 2-[(3alpha-hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid 2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonate 2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonic acid 3a-Hydroxy-5b-cholanoyltaurine 3a-Hydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide Cholane ethanesulfonic acid deriv. Lithocholic acid taurine conjugate Lithocholic acid taurine conjugic acid N-(3a-hydroxy-5b-cholan-24-oyl)-Taurine taurolithocholate Taurolithocholic acid C26H45NO5S 483.704 483.301844245 2-[(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 acid 2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid 516-90-5 C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C 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 QBYUNVOYXHFVKC-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 derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 3-alpha-hydroxysteroids Alkanesulfonic acids Carbonyl compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Monohydroxy bile acids, alcohols and derivatives N-acyl amines Organic oxides Organonitrogen compounds Organopnictogen compounds Organosulfonic acids Secondary alcohols Secondary carboxylic acid amides Sulfonyls 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alkanesulfonic acid Carbonyl group Carboxamide group Carboxylic acid derivative Cyclic alcohol Fatty acyl Fatty amide Hydrocarbon derivative Hydroxy bile acid, alcohol, or derivatives Hydroxysteroid Monohydroxy bile acid, alcohol, or derivatives N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfonic acid or derivatives Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfonic acid Organosulfonic acid or derivatives Organosulfur compound Secondary alcohol Secondary carboxylic acid amide Sulfonyl Taurinated bile acid Liquid logp 2.10 ALOGPS logs -6.24 ALOGPS solubility 2.77e-04 g/l ALOGPS logp 2.48 ChemAxon pka_strongest_acidic -0.63 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac 2-[(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 acid ChemAxon average_mass 483.704 ChemAxon mono_mass 483.301844245 ChemAxon smiles C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C ChemAxon formula C26H45NO5S ChemAxon inchi 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 ChemAxon inchikey QBYUNVOYXHFVKC-LVMSMGIASA-N ChemAxon polar_surface_area 103.7 ChemAxon refractivity 129.09 ChemAxon polarizability 55.73 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::CMs 17054 Specdb::CMs 37722 Specdb::MsMs 82389 Specdb::MsMs 82390 Specdb::MsMs 82391 Specdb::MsMs 143733 Specdb::MsMs 143734 Specdb::MsMs 143735 HMDB00722 36259 #<Reference:0x000055ce33619f98> #<Reference:0x000055ce33619de0> #<Reference:0x000055ce33619c28> #<Reference:0x000055ce33619a70> #<Reference:0x000055ce336198b8> #<Reference:0x000055ce33619700> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Bile salt sulfotransferase Q06520 SULT2A1