Metabolite Card
Formula: C26H45NO8S2 (563.2586)
SMILES: [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O
Synonyms [en]
Taurolithocholate sulfate; 3alpha-sulfatolithocholyltaurine; taurolithocholic acid 3-sulfate; TLC-S; taurolithocholic acid sulfate; (3alpha-sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonate
Last reviewed on 2024-06-28.
Cite this Page
Taurolithocholate sulfate. 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: BioCAD00000018216). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Taurolithocholic acid 3-sulfate is a sulfated bile acid. Under normal circumstances, bile acid sulfation is a minor pathway. However in the presence of cholestasis, the fraction of the bile acid pool which is sulfated increases. Sulfation of bile acids increases the aqueous solubility of the amphipathic compounds and results in more efficient renal clearance as well as in decreased reabsorption from the intestinal lumen. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487, 16037564, 12576301, 11907135).
DBLinks
- CAS Registry Number: 15324-65-9
- PubChem CID: 440071
- ChEBI: 17864
- HMDB: HMDB0002580
- LipidMaps: LMST05020003
- KEGG: C03642
- BioCyc:
- NCBI MeSH: taurolithocholic acid 3-sulfate
- Wikipedia:
Other DBLinks
- CAS Registry Number: 15324-65-9
- PubChem: 440071
- ChEBI: ChEBI:17864
- HMDB: HMDB0002580
- HMDB: HMDB02580
- LipidMaps: LMST05020003
- KEGG: C03642
- NCBI MeSH: taurolithocholic acid 3-sulfate
- RefMet: RM0135843
- MoNA: KO001953
- MoNA: LipidBlast2022_063694
- MoNA: LipidBlast2022_199586
- MoNA: NU000841
- MoNA: NU000842
- MoNA: NU000843
- MoNA: NU000844
- MoNA: NU000845
- Metlin: METLIN_6716
- Coconut NaturalProduct: CNP0079828.1
Class / Ontology
- WishartLab ClassyFire: [Bile acids, alcohols and derivatives] Bile acids, alcohols and derivatives
- RefMet: [C24 bile acids] C24 bile acids
- LipidMaps: [Sulfates [ST0502]] Sulfates [ST0502]
- ChEBI: [CHEBI:17864] taurolithocholic acid sulfate
- Coconut NaturalProduct: [Cholane steroids] Cholane steroids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R03987 | 2.8.2.14 | 3'-phosphoadenylylsulfate:taurolithocholate sulfotransferase |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| Reactome:R-BTA-9958517 | SLC-mediated bile acid transport |
| Reactome:R-CEL-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-CFA-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-SSC-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-XTR-9958517 | SLC-mediated bile acid transport |
| Reactome:R-BTA-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-DME-9958517 | SLC-mediated bile acid transport |
| Reactome:R-MMU-9958517 | SLC-mediated bile acid transport |
| Reactome:R-RNO-9958517 | SLC-mediated bile acid transport |
| Reactome:R-XTR-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-CEL-9958517 | SLC-mediated bile acid transport |
| Reactome:R-CFA-9958517 | SLC-mediated bile acid transport |
| Reactome:R-HSA-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-SSC-9958517 | SLC-mediated bile acid transport |
| Reactome:R-DME-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-HSA-9958517 | SLC-mediated bile acid transport |
| Reactome:R-MMU-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-RNO-9955298 | SLC-mediated transport of organic anions |
| Reactome:R-BTA-1430728 | Metabolism |
| Reactome:R-CEL-211859 | Biological oxidations |