Tauro-β-muricholic Acid (sodium salt)

• CAT Number: R066738
• CAS Number: 145022-92-0
• Molecular Formula: C26H44NO7S • Na
• Molecular Weight: 537.7
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: sodium;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]ethanesulfonate
• InChI: InChI=1S/C26H45NO7S.Na/c1-15(4-7-21(29)27-12-13-35(32,33)34)17-5-6-18-22-19(9-11-25(17,18)2)26(3)10-8-16(28)14-20(26)23(30)24(22)31;/h15-20,22-24,28,30-31H,4-14H2,1-3H3,(H,27,29)(H,32,33,34);/q;+1/p-1/t15-,16-,17-,18+,19+,20+,22+,23+,24-,25-,26-;/m1./s1
• InChIKey: NYXROOLWUZIWRB-GPHZYVDLSA-M
• SMILES: C[C@H](CCC(NCCS([O-])(=O)=O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@H](O)[C@@H](O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C.[Na+]

Tauro-β-muricholic acid (TβMCA; CAS 145022-92-0) is a potent competitive and reversible antagonist of the farnesoid X receptor (FXR) (IC50 = 40 µM) that binds bile acids. TβMCA accumulates in germ-free mice under normal conditions but is reduced after colonization with feces from a human donor. TβMCA is increased in the intestines of mice resistant to high-fat diet-induced obesity, fatty liver, and diabetes.

Reference

1.Sayin, S.I.,Wahlström, A.,Felin, J., et al. Gut microbiota regulates bile acid metabolism by reducing the levels of tauro-beta-muricholic acid, a naturally occurring FXR antagonist. Cell Metab. 17(2), 225-235 (2013).