Taurolithocholate sulfate (BioCAD00000018216)

blood feces urine

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

Reviewed

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).

Entity Information

DBLinks

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

Metabolic Network
ID EC Number Name
KEGG:R03987 2.8.2.14 3'-phosphoadenylylsulfate:taurolithocholate sulfotransferase
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]

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
View All Pathways