| 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 canalicliar contractions and the canalicliar bile secretion, possibly by acting directly on the canalicliar 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 canalicliar 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
2-[(3alpha-Hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethaneslifonic acidHMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethaneslifonateHMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethaneslifonic acidHMDB
3a-Hydroxy-5b-cholanoyltaurineHMDB
3a-Hydroxy-N-(2-slifoethyl)-5b-cholan-24-amideHMDB
Cholane ethaneslifonic acid deriv.HMDB
Lithocholic acid taurine conjugateHMDB
Lithocholic acid taurine conjugic acidHMDB
N-(3a-Hydroxy-5b-cholan-24-oyl)-taurineHMDB
TaurolithocholateHMDB
Taurolithocholic acidHMDB
Lithocholate, taurineMeSH
Taurine lithocholateMeSH
Taurolithocholic acid, monosodium saltMeSH
Acid, taurolithocholicMeSH
| Chemical Formlia |
C26H45NO5S
| Average Molecliar Weight |
483.704
| Monoisotopic Molecliar Weight |
483.301844245
| IUPAC Name |
2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-slifonic acid
| Traditional Name |
2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethaneslifonic acid
| CAS Registry Number |
516-90-5
| 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 Key |
QBYUNVOYXHFVKC-LVMSMGIASA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected 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 Emlisifiers
| Cellliar locations |
Extracellliar
| Physical Properties |
| State |
Liquid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point212 – 213 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
| Biofluid Locations |
Bile
Blood
Feces
| Tissue Location |
Gall Bladder
Intestine
| Pathways |
| Name |
SMPDB Link |
KEGG 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 |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BileDetected and Quantified370.0 (350.0-380.0) uMAdlit (>18 years old)BothNormal
16548228
details
BloodDetected and Quantified0.614 +/- 0.013 uMAdlit (>18 years old)Not SpecifiedNormal
16182619
details
BloodDetected and Quantified1.810 +/- 0.002 uMAdlit (>18 years old)Not Specified
Normal
16182619
details
FecesDetected and Quantified0.51 +/- 0.40 nmol/g of fecesNot SpecifiedNot Specified
Normal
22664055
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022203
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
C02592
| BioCyc ID |
TAUROLITHOCHOLATE
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00722
| Metagene Link |
HMDB00722
| METLIN ID |
5690
| PubChem Compound |
53477716
| PDB ID |
Not Available
| ChEBI ID |
36259
Product: Hemin
References |
| 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. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General 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:16548228 ]
- 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:9518169 ]
- 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. [PubMed:16332456 ]
- 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. [PubMed:16981261 ]
- 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. [PubMed:15763547 ]
- 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. [PubMed: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-sulfate |
details |
PMID: 20832753