Key facts
CAS number:459789-99-2,
Purity:>95%,
Form:SolidSee storage information,
Molecular weight:420.6 Da,
Molecular formula:C26H44O4,
PubChem:447715,
Nature:Synthetic,
Solubility:Soluble in ethanol to 50 mMSoluble in DMSO to 75 mM,
Biochemical name:Obeticholic acid,
Biological description:Potent and selective FXR agonist (EC50 = 99 nM). Dual FXR/GP-BAR1 ligand. Induces preadiopocyte differentiation. Induces apoptosis. Shows anticholeretic and anti-inflammatory effects and regulates adipose cell function in vivo. Orally active.,
Canonical smiles:CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)O)C)C)O,
Isomeric smiles:CC[C@@H]1[C@@H]2C[C@@H](CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H]1O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)O,
InChi:InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1,
InChiKey:ZXERDUOLZKYMJM-ZWECCWDJSA-N,
IUPAC Name:(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-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]pentanoic acid
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions--20°C, Appropriate long-term storage conditions--20°C, Storage information-Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
The GPCR TGR5 also known as G protein-coupled bile acid receptor 1 (GPBAR1) serves as a membrane receptor activated by bile acids. TGR5 is part of the G-protein coupled receptor (GPCR) superfamily and has an approximate molecular weight of 35-40 kDa. This receptor is mainly expressed in brown adipose tissue intestine liver and immune cells where it plays significant roles in multiple physiological processes.
Biological function summary
This receptor modulates energy homeostasis and immune regulation by associating with bile acids. Through activation by bile acids like 6-ECDCA TGR5 facilitates energy expenditure by increasing thermogenesis in brown adipose tissue. The receptor also impacts inflammatory response in immune cells suggesting a role in inflammation regulation. TGR5 does not form part of a larger protein complex under normal physiological conditions.
Pathways
The TGR5 receptor participates in metabolic and anti-inflammatory pathways. It interacts with proteins such as FXR (Farnesoid X Receptor) which acts as a nuclear receptor for bile acids. The interaction between TGR5 and FXR forms part of the bile acid signaling pathway regulating metabolic processes like glucose homeostasis and preventing excessive inflammation through immune cell modulation.
TGR5 has associations with metabolic syndromes and inflammatory bowel disease. The receptor's influence on energy expenditure and insulin sensitivity connects it to metabolic disorders such as obesity. Additionally TGR5 affects the inflammatory response and its interaction with other immune-modulating receptors suggests involvement in inflammatory bowel disease. The receptor shares functional pathways with FXR agonists linking its activity to both metabolic and inflammatory conditions.
