Gly-β-MCA is a bile acid acting as an oral and potent farnesoid X receptor (FXR) inhibitor with the potential to be used for the treatment of metabolic disorders.
Physicochemical Properties
| Molecular Formula | C26H43NO6 |
| Molecular Weight | 465.623 |
| Exact Mass | 465.309 |
| CAS # | 66225-78-3 |
| PubChem CID | 137333454 |
| Appearance | White to off-white solid powder |
| LogP | 3.3 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 33 |
| Complexity | 759 |
| Defined Atom Stereocenter Count | 11 |
| SMILES | C[C@@H]([C@@]1([H])CC[C@@]2([H])[C@@]3([H])[C@]([C@]4(CC[C@@H](O)C[C@H]4[C@H](O)[C@@H]3O)C)([H])CC[C@]12C)CCC(NCC(O)=O)=O |
| InChi Key | ZQYUKJFJPJDMMR-IIWZPVADSA-N |
| InChi Code | InChI=1S/C26H43NO6/c1-14(4-7-20(29)27-13-21(30)31)16-5-6-17-22-18(9-11-25(16,17)2)26(3)10-8-15(28)12-19(26)23(32)24(22)33/h14-19,22-24,28,32-33H,4-13H2,1-3H3,(H,27,29)(H,30,31)/t14-,15-,16-,17+,18+,19+,22+,23+,24-,25-,26-/m1/s1 |
| Chemical Name | 2-[[(4R)-4-[(3R,5R,6S,7R,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-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) |
Biological Activity
| ln Vitro | Gly-β-MCA is a bile acid that exhibits strong intestinal-selective inhibition of the farnesoid X receptor (FXR) [1]. The hydrolysis of BSH is resisted by Gly-β-MCA (Gly-MCA) [1]. |
| ln Vivo | Without causing systemic, hepatic, or intestinal toxicity in mice, Gly-β-MCA (Gly-MCA, oral, 10 and 50 mg/kg) prevents and controls diet-induced and hereditary obesity, insulin resistance, and hepatic steatosis [1]. It is possible that Gly-MCA does not cause intestinal inflammation because it does not raise fecal LCN-2 levels [1]. |
| References |
[1]. Intestine-selective farnesoid X receptor inhibition improves obesity-related metabolic dysfunction. Nat Commun. 2015 Dec 15;6:10166. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~214.77 mM) H2O : < 0.1 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.47 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 (4.47 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. Solubility in Formulation 3: ≥ 2.08 mg/mL (4.47 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 | 2.1477 mL | 10.7384 mL | 21.4767 mL | |
| 5 mM | 0.4295 mL | 2.1477 mL | 4.2953 mL | |
| 10 mM | 0.2148 mL | 1.0738 mL | 2.1477 mL |