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Chenodeoxycholic Acid

CAT: 0013-GTR19161938-04Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161938-04Size:100 mg
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Description
A potent natural bile acid at stimulating the nuclear bile acid receptor, farnesoid X receptor (FXR) ; increases plasma concentrations of GLP-1, C-peptide, glucagon, peptide YY, neurotensin, total bile acids, and FGF19 significantly compared with placebo; also activates NLRP3 inflammasome and contributes to cholestatic liver fibrosis.Other Indication Approved (In Vitro) :Chenodeoxycholic acid (CDCA) and Deoxycholic acid (DCA) both inhibit 11 beta HSD2 with IC50 values of 22 mM and 38 mM, respectively and causes cortisol-dependent nuclear translocation and increases transcriptionalactivity of mineralocorticoid receptor (MR) . Chenodeoxycholic acid is able to stimulate Ishikawa cell growth by inducing a significant increase in Cyclin D1 protein and mRNA expression through the activation of the membrane G protein-coupled receptor (TGR5) -dependent pathway. Chenodeoxycholic acid (CDCA) induces LDL receptor mRNA levels approximately 4 fold and mRNA levels for HMG-CoA reductase and HMG-CoA synthase two fold in a cultured human hepatoblastoma cell line, Hep G2. Chenodeoxycholic acid-induced Isc is inhibited (≥67%) by Bumetanide, BaCl2, and the cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor CFTRinh-172. Chenodeoxycholic acid-stimulated Isc is decreased 43% by the adenylate cyclase inhibitor MDL12330A and Chenodeoxycholic acid increases intracellular cAMP concentration. Chenodeoxycholic acid treatment activates C/EBPβ, as shown by increases in its phosphorylation, nuclear accumulation, and expression in HepG2 cells. Chenodeoxycholic acid enhances luciferase gene transcription from the construct containing -1.65-kb GSTA2 promoter, which contains C/EBP response element (pGL-1651) . Chenodeoxycholic acid treatment activates AMP-activated protein kinase (AMPK), which leads to extracellular signal-regulated kinase 1/2 (ERK1/2) activation, as evidenced by the results of experiments using a dominant-negative mutant of AMPKα and chemical inhibitor.
CAS Number
474-25-9
Product Name Alternative
CDCA
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 3.6 mg/mL
Smiles
C[C@@H] ([C@H]1CC[C@@]2 ([H]) [C@]3 ([H]) [C@H] (O) C[C@]4 ([H]) C[C@H] (O) CC[C@]4 (C) [C@@]3 ([H]) CC[C@]12C) CCC (O) =O
Molecular Formula
C24H40O4
Molecular Weight
392.572
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
Cholan-24-oic acid, 3,7-dihydroxy-, (3α,5β,7α) -

Chemical Information

Chenodeoxycholic Acid

Chenodiol can cause developmental toxicity according to state or federal government labeling requirements.

CAS Number474-25-9
PubChem CID10133
IUPAC Name(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-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
Molecular FormulaC24H40O4
Molecular Weight392.6
XLogP4.9
Topological Polar Surface Area77.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Heavy Atom Count28
Formal Charge0
Complexity605
SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChI
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChIKey
RUDATBOHQWOJDD-BSWAIDMHSA-N
Chemical Structure
2D Structure
2D structure of Chenodeoxycholic Acid
CAS: 474-25-9
CID: 10133
Formula: C24H40O4
MW: 392.6
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight392.6
XLogP34.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass392.29265975
Monoisotopic Mass392.29265975
Topological Polar Surface Area77.8 Ų
Heavy Atom Count28
Formal Charge0
Complexity605
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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