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AB144246

6-ECDCA (INT-747), FXR agonist

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(1 Publication)

MW 420.6 Da, Purity >95%. 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.
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Chemical Structure - 6-ECDCA (INT-747), FXR agonist (AB144246)
  • Chemical Structure

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Chemical Structure - 6-ECDCA (INT-747), FXR agonist (AB144246)

2D chemical structure image of ab144246, 6-ECDCA (INT-747), FXR agonist

Key facts

CAS number

459789-99-2

Purity

>95%

Form

Solid

form

Molecular weight

420.6 Da

Molecular formula

C<sub>2</sub><sub>6</sub>H<sub>4</sub><sub>4</sub>O<sub>4</sub>

PubChem

447715

Nature

Synthetic

Solubility

Soluble in ethanol to 50 mM

Soluble 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

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Complementary Products

Primary Antibodies

AB129089

Anti-FXR1 antibody [EPR7932]

RabMAb|Recombinant|KO Validated

Immunocytochemistry/ Immunofluorescence - Anti-FXR1 antibody [EPR7932] (AB129089)

  • 5
  • 1
Primary Antibodies

AB85606

Anti-Bile Acid Receptor NR1H4 antibody

Immunocytochemistry/ Immunofluorescence - Anti-Bile Acid Receptor NR1H4 antibody (AB85606)

  • 0
  • 0
Primary Antibodies

AB72608

Anti-GPCR TGR5 antibody

BOND RX™ Validated

Western blot - Anti-GPCR TGR5 antibody (AB72608)

  • 0
  • 0
Secondary Antibodies

AB150077

Goat Anti-Rabbit IgG H&L (Alexa Fluor® 488)

Immunocytochemistry/ Immunofluorescence - Goat Anti-Rabbit IgG H&L (Alexa Fluor® 488) (AB150077)

  • 5
  • 20
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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
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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.
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Product protocols

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Publications (1)

Recent publications for all applications. Explore the full list and refine your search

Scientific reports 7:9815 PubMed28852062

2017

Farnesoid X receptor activation protects the kidney from ischemia-reperfusion damage.

Applications

Unspecified application

Species

Unspecified reactive species

Zhibo Gai,Lei Chu,Zhenqiang Xu,Xiaoming Song,Dongfeng Sun,Gerd A Kullak-Ublick
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