Taurocholic acid 3-sulfate
From DrugPedia: A Wikipedia for Drug discovery
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Description
Taurocholic acid 3-sulfate is a sulfated bile acid. It is a sulfate salt of taurocholic acid and is also known as cholaic acid, cholyltaurine, or acidum cholatauricum. 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 bile of mammals. The distinction between different bile acids is minute, depends only on 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)
General Properties
*Molecular Weight
595.77
*Molecular Formula
C26H45NO10S2
*IUPAC NAME
2-[[(3a,5b,7a,12a)-7,12-dihydroxy-24-oxo-3-(sulfooxy)cholan-24-yl]amino]-ethanesulfonic acid
*Canonical Smiles
CC(CCC(=O)NCCS(O)(=O)=O)C1CCC2C3C(O)CC4CC(CCC4(C)C3CC(O)C12C)OS(O)(=O)=O
*Isomeric Smiles
C[C@H](CCC(=O)NCCS(O)(=O)=O)[C@H]1CCC2C3[C@H](O)C[C@@H]4C[C@@H](CC[C@]4(C)C3C[C@H](O)[C@]12C)OS(O)(=O)=O
PhysioChemical Properties
*Melting Point
*LogP
*Water Solubility
External Links
- [1]Human Metabolome DataBase
