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Glycohyodeoxycholic acid

Cat No.:V38739 Purity: ≥98%
Glycohyodeoxycholic acid is the major metabolite of Hyodeoxycholic acid in the human body and has a preventive effect on the formation of gallstones.
Glycohyodeoxycholic acid
Glycohyodeoxycholic acid Chemical Structure CAS No.: 13042-33-6
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25mg
50mg
100mg
250mg
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Product Description
Glycohyodeoxycholic acid is the major metabolite of Hyodeoxycholic acid in the human body and has a preventive effect on the formation of gallstones.
Glycohyodeoxycholic acid is a major metabolite of the secondary bile acid hyodeoxycholic acid in humans. It has a molecular formula of C26H43NO5 and a molecular weight of 449.62. It has been identified as a biomarker with a negative correlation to the severity of non-alcoholic fatty liver disease (NAFLD). It also has preventative effects on gallstone formation.
Biological Activity I Assay Protocols (From Reference)
Targets
Glycohyodeoxycholic acid targets bile acid metabolism and lipid homeostasis. As a bile acid, it can interact with nuclear receptors such as the farnesoid X receptor (FXR). It inhibits the activity of cholesterol 7α-hydroxylase, the rate-limiting enzyme in bile acid synthesis. This leads to a decrease in bile acid production and cholesterol secretion.
ln Vitro
In vitro, glycohyodeoxycholic acid is used to model bile acid aggregation under physiological pH and to evaluate its role in lipid absorption and transport systems. It is also used to study its effects on cholesterol crystallization. Its inhibitory activity on cholesterol 7α-hydroxylase can be assessed in enzyme assays.
ln Vivo
In vivo, glycohyodeoxycholic acid is a major human metabolite of hyodeoxycholic acid. Supplementation with glycohyodeoxycholic acid in prairie dogs fed a lithogenic diet decreases the frequency of cholesterol crystals in the gallbladder. Its levels in serum are negatively correlated with the severity of NAFLD.
Enzyme Assay
In vitro assays for glycohyodeoxycholic acid are biochemical. It can be used as a substrate to study the activity of bile acid-modifying enzymes. Its effects on cholesterol crystallization can be assessed in model bile systems by measuring the time to crystal formation. Its ability to inhibit cholesterol 7α-hydroxylase can be measured in liver microsome assays.
Cell Assay
Glycohyodeoxycholic acid can be used in cellular assays to study its effects on hepatocytes. Cells are treated with the compound, and its effects on the expression of genes involved in bile acid synthesis (e.g., CYP7A1) and lipid metabolism are measured by qPCR. Its effects on lipid accumulation can be assessed using Oil Red O staining.
Animal Protocol
In vivo animal experiments with glycohyodeoxycholic acid are conducted in models of gallstone disease, such as the lithogenic diet-fed prairie dog. Animals are administered the compound orally, and its effects on gallbladder cholesterol crystals, bile composition, and liver enzyme activity are assessed. Its utility as a biomarker for NAFLD can be studied in diet-induced obesity models.
ADME/Pharmacokinetics
Glycohyodeoxycholic acid is a metabolite and its pharmacokinetics are related to bile acid metabolism. It has a molecular weight of 449.62. It is soluble in DMSO at ≥200 mg/mL and is typically stored as a powder at -20°C for up to 3 years.
Toxicity/Toxicokinetics
Glycohyodeoxycholic acid is considered to have low toxicity as it is an endogenous metabolite. However, comprehensive toxicological data are not extensively published. The compound is intended for research use only and is not approved for human therapeutic use.
References

[1]. Intestinal absorption, excretion, and biotransformation of hyodeoxycholic acid in man. J Lipid Res. 1983 May;24(5):604-13.

[2]. Hyodeoxycholic acid: a new approach to gallstone prevention. Am J Surg. 1985 Jan;149(1):126-32.

Additional Infomation
Glycine deoxycholic acid is a combination of bile acid and glycine.
Glycohyodeoxycholic acid is a major human metabolite of hyodeoxycholic acid. It has preventative effects on gallstone formation and is a potential biomarker for NAFLD. It inhibits cholesterol 7α-hydroxylase activity and is used in research on bile acid metabolism and lipid disorders.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H43NO5
Molecular Weight
449.62332
Exact Mass
449.314
CAS #
13042-33-6
PubChem CID
114611
Appearance
White to off-white solid powder
Density
1.162g/cm3
Boiling Point
655.6ºC at 760mmHg
Flash Point
350.3ºC
Vapour Pressure
5.74E-20mmHg at 25°C
Index of Refraction
1.546
LogP
3.985
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Heavy Atom Count
32
Complexity
727
Defined Atom Stereocenter Count
10
SMILES
C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChi Key
SPOIYSFQOFYOFZ-BRDORRHWSA-N
InChi Code
InChI=1S/C26H43NO5/c1-15(4-7-23(30)27-14-24(31)32)18-5-6-19-17-13-22(29)21-12-16(28)8-10-26(21,3)20(17)9-11-25(18,19)2/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17+,18-,19+,20+,21+,22+,25-,26-/m1/s1
Chemical Name
2-[[(4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~556.03 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.63 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (4.63 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (4.63 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2241 mL 11.1205 mL 22.2410 mL
5 mM 0.4448 mL 2.2241 mL 4.4482 mL
10 mM 0.2224 mL 1.1121 mL 2.2241 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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