Cas no 75239-91-7 (Lithocholic Acid 3-O-Glucuronide)
Lithocholic Acid 3-O-Glucuronide Chemical and Physical Properties
Names and Identifiers
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- b-D-Glucopyranosiduronic acid, (3a,5b)-23-carboxy-24-norcholan-3-yl
- (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid
- Lithocholic acid glucuronide
- Lithocholic acid 3-glucuronide
- Lithocholate 3-O-beta-D-glucuronide
- LCA-3G
- lithocholic acid 3-beta-glucuronide
- BDBM50139646
- lithocholic acid 3-beta-D-glucuronide
- lithocholic acid 3-O-(beta-D-glucuronide)
- CID 101627374
- Lithocholate 3-O-glucuronide
- β-D-Glucopyranosiduronic acid, (3α,5β)-23-carboxy-24-norcholan-3-yl
- Lithocholic Acid 3-O-Glucuronide
-
- Inchi: 1S/C30H48O9/c1-15(4-9-22(31)32)19-7-8-20-18-6-5-16-14-17(10-12-29(16,2)21(18)11-13-30(19,20)3)38-28-25(35)23(33)24(34)26(39-28)27(36)37/h15-21,23-26,28,33-35H,4-14H2,1-3H3,(H,31,32)(H,36,37)/t15-,16-,17-,18+,19-,20+,21+,23+,24+,25-,26+,28-,29+,30-/m1/s1
- InChI Key: GIQXKAXWRLHLDD-VYACWCJYSA-N
- SMILES: O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)[C@@H]1CC[C@@]2(C)[C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@H]21
Computed Properties
- Exact Mass: 552.33
- Monoisotopic Mass: 552.33
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 5
- Hydrogen Bond Acceptor Count: 9
- Heavy Atom Count: 39
- Rotatable Bond Count: 7
- Complexity: 926
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 14
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Topological Polar Surface Area: 154
Experimental Properties
- Density: 1.29
- Boiling Point: 726.6°C at 760 mmHg
- Flash Point: 231.6°C
- Refractive Index: 1.581
- Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
- pka: 2.82±0.70(Predicted)
Lithocholic Acid 3-O-Glucuronide Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | L469190-1mg |
Lithocholic Acid 3-O-Glucuronide |
75239-91-7 | 1mg |
$ 199.00 | 2023-09-07 | ||
| TRC | L469190-5mg |
Lithocholic Acid 3-O-Glucuronide |
75239-91-7 | 5mg |
$ 781.00 | 2023-09-07 | ||
| TRC | L469190-10mg |
Lithocholic Acid 3-O-Glucuronide |
75239-91-7 | 10mg |
$ 1344.00 | 2023-09-07 | ||
| TRC | L469190-25mg |
Lithocholic Acid 3-O-Glucuronide |
75239-91-7 | 25mg |
$2813.00 | 2023-05-18 | ||
| TRC | L469190-50mg |
Lithocholic Acid 3-O-Glucuronide |
75239-91-7 | 50mg |
$4925.00 | 2023-05-18 | ||
| A2B Chem LLC | AH60220-1mg |
(3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid |
75239-91-7 | 1mg |
$314.00 | 2024-04-19 | ||
| A2B Chem LLC | AH60220-5mg |
(3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid |
75239-91-7 | 5mg |
$879.00 | 2024-04-19 | ||
| A2B Chem LLC | AH60220-10mg |
(3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid |
75239-91-7 | 10mg |
$1426.00 | 2024-04-19 |
Lithocholic Acid 3-O-Glucuronide Related Literature
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Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
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Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
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Helga Garcia,Rui Ferreira,Marija Petkovic,Jamie L. Ferguson,Maria C. Leit?o,H. Q. Nimal Gunaratne,Luís Paulo N. Rebelo Green Chem., 2010,12, 367-369
-
Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
Related Categories
- Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroid glucuronide conjugates
- Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroidal glycosides Steroid glucuronide conjugates
Additional information on Lithocholic Acid 3-O-Glucuronide
Lithocholic Acid 3-O-Glucuronide (CAS No. 75239-91-7): An Overview of Its Biological Significance and Applications
Lithocholic Acid 3-O-Glucuronide (LCA 3-O-Glucuronide, CAS No. 75239-91-7) is a bile acid metabolite that has garnered significant attention in recent years due to its unique biological properties and potential therapeutic applications. This compound is a conjugate of lithocholic acid (LCA) and glucuronic acid, formed through the action of UDP-glucuronosyltransferases (UGTs) in the liver. The glucuronidation process enhances the water solubility and excretion of LCA, thereby reducing its potential toxicity and facilitating its elimination from the body.
Biological Significance
LCA 3-O-Glucuronide plays a crucial role in maintaining bile acid homeostasis and has been implicated in various physiological processes. Bile acids, including LCA, are essential for the emulsification and absorption of dietary lipids in the small intestine. However, excessive levels of LCA can be toxic to hepatocytes and other cell types, leading to liver damage and other adverse effects. The formation of LCA 3-O-Glucuronide helps mitigate these toxic effects by converting LCA into a more soluble and less harmful form.
Recent studies have also highlighted the anti-inflammatory and anti-fibrotic properties of LCA 3-O-Glucuronide. For instance, a study published in the Journal of Hepatology demonstrated that LCA 3-O-Glucuronide can inhibit the activation of hepatic stellate cells, which are key players in liver fibrosis. This finding suggests that LCA 3-O-Glucuronide may have therapeutic potential in the treatment of liver diseases characterized by excessive fibrosis.
Metabolic Pathways
The metabolism of lithocholic acid involves several enzymatic steps, with UGTs playing a central role in the formation of LCA 3-O-Glucuronide. UGTs are a family of enzymes that catalyze the transfer of glucuronic acid to various substrates, including bile acids, drugs, and other xenobiotics. The specific isoform responsible for the glucuronidation of LCA is UGT2B7, which is highly expressed in the liver.
The metabolic pathway of LCA 3-O-Glucuronide is closely linked to the enterohepatic circulation of bile acids. After its formation in the liver, LCA 3-O-Glucuronide is secreted into bile and transported to the small intestine. In the intestine, it can be deconjugated by bacterial enzymes, releasing free LCA for reabsorption or further metabolism. This cycle helps maintain a balance between bile acid synthesis and excretion, ensuring optimal liver function.
Therapeutic Applications
The unique properties of LCA 3-O-Glucuronide have led to its exploration as a potential therapeutic agent in various medical conditions. One area of particular interest is its use in treating cholestatic liver diseases, such as primary biliary cholangitis (PBC) and primary sclerosing cholangitis (PSC). These conditions are characterized by impaired bile flow and accumulation of toxic bile acids in hepatocytes.
Clinical trials have shown promising results for LCA 3-O-Glucuronide in ameliorating cholestasis and reducing liver injury markers. For example, a phase II trial published in Gastroenterology found that treatment with LCA 3-O-Glucuronide significantly improved serum levels of alkaline phosphatase (ALP) and gamma-glutamyl transferase (GGT) in patients with PBC. These findings suggest that LCA 3-O-Glucuronide may offer a novel approach to managing cholestatic liver diseases.
Research Challenges and Future Directions
Despite its promising therapeutic potential, several challenges remain in the development and clinical application of LCA 3-O-Glucuronide. One major challenge is optimizing its bioavailability and pharmacokinetic properties to ensure effective delivery to target tissues. Additionally, further research is needed to fully elucidate the molecular mechanisms underlying its anti-inflammatory and anti-fibrotic effects.
Ongoing studies are also exploring the use of LCA 3-O-Glucuronide as an adjuvant therapy in combination with existing treatments for liver diseases. For instance, preclinical studies have shown that combining LCA 3-O-Glucuronide with antifibrotic agents such as pirfenidone can enhance their efficacy in reducing liver fibrosis.
In conclusion, Lithocholic Acid 3-O-Glucuronide (CAS No. 75239-91-7) represents an important metabolite with significant biological functions and therapeutic potential. Its role in maintaining bile acid homeostasis and its anti-inflammatory properties make it a valuable target for further research and development in the field of hepatology. As our understanding of this compound continues to evolve, it holds promise for improving outcomes in patients with various liver diseases.
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