Metabolite Card
Formula: C26H45NO5S (483.3018)
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
Synonyms [en]
Taurolithocholate; Taurolithocholic Acid; Lithocholyltaurine; N-(3alpha-hydroxy-5beta-cholan-24-oyl)-taurine; ST 24:1;O2;T; Lithocholic acid taurine conjugate
Last reviewed on 2024-06-28.
Cite this Page
Taurolithocholate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000018215). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
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).
DBLinks
- CAS Registry Number: 516-90-5
- PubChem CID: 439763
- ChEBI: 17179
- HMDB: HMDB0000722
- LipidMaps: LMST05040003
- KEGG: C02592
- BioCyc:
- NCBI MeSH: Taurolithocholic Acid
- Wikipedia: Taurolithocholic_acid
Other DBLinks
- CAS Registry Number: 516-90-5
- CAS Registry Number: 6042-32-6
- PubChem: 10595
- PubChem: 439763
- PubChem: 451488
- PubChem: 53477716
- ChEBI: ChEBI:17179
- ChEBI: ChEBI:36259
- HMDB: HMDB0000722
- HMDB: HMDB00722
- LipidMaps: LMST05040003
- KEGG: C02592
- KEGG: C03642
- NCBI MeSH: Taurolithocholic Acid
- Wikipedia: Taurolithocholic_acid
- RefMet: RM0011885
- MoNA: CCMSLIB00005435494
- MoNA: CCMSLIB00005435495
- MoNA: CCMSLIB00005435496
- MoNA: CCMSLIB00005435588
- MoNA: CCMSLIB00005435589
- MoNA: CCMSLIB00005435590
- MoNA: CCMSLIB00005435591
- MoNA: CCMSLIB00005435592
- MoNA: CCMSLIB00005463872
- MoNA: KO001954
- MoNA: KO001955
- MoNA: KO001956
- MoNA: KO001957
- MoNA: LipidBlast2022_199808
- MoNA: MoNA032646
- MoNA: MoNA032649
- MoNA: MoNA032650
- MoNA: MoNA032672
- MoNA: MoNA032673
- MoNA: MoNA032677
- MoNA: MoNA034652
- MoNA: MoNA034654
- MoNA: MoNA034655
- MoNA: MoNA035029
- MoNA: MoNA035030
- MoNA: MoNA035031
- MoNA: MoNA035380
- MoNA: MoNA035384
- MoNA: MoNA035385
- MoNA: MoNA036376
- MoNA: MoNA036377
- MoNA: MoNA036379
- MoNA: MoNA036564
- MoNA: MoNA036565
- MoNA: MoNA036570
- MoNA: MoNA036768
- MoNA: MoNA036771
- MoNA: MoNA036774
- MoNA: MoNA038094
- MoNA: MoNA038152
- MoNA: MoNA038303
- MoNA: MoNA038683
- MoNA: MoNA038725
- MoNA: MoNA038815
- MoNA: RP006101
- MoNA: RP006102
- MoNA: RP006103
- Metlin: METLIN_5690
- Coconut NaturalProduct: CNP0409667.2
- Coconut NaturalProduct: CNP0409667.3
Class / Ontology
- WishartLab ClassyFire: [Bile acids, alcohols and derivatives] Bile acids, alcohols and derivatives
- RefMet: [C24 bile acids] C24 bile acids
- LipidMaps: [Taurine conjugates [ST0504]] Taurine conjugates [ST0504]
- ChEBI: [CHEBI:36259] taurolithocholic acid
- Coconut NaturalProduct: [Cholane steroids] Cholane steroids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R03987 | 2.8.2.14 | 3'-phosphoadenylylsulfate:taurolithocholate sulfotransferase |
| Rhea:RHEA:14014 | 2.8.2.14 | taurolithocholate + 3'-phosphoadenylyl sulfate => taurolithocholate 3-sulfate + adenosine 3',5'-bisphosphate + H+ |
| Rhea:RHEA:14015 | 2.8.2.14 | taurolithocholate 3-sulfate + adenosine 3',5'-bisphosphate + H+ => taurolithocholate + 3'-phosphoadenylyl sulfate |
| Rhea:RHEA:14016 | 2.8.2.14 | taurolithocholate + 3'-phosphoadenylyl sulfate <=> taurolithocholate 3-sulfate + adenosine 3',5'-bisphosphate + H+ |