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Chenodeoxycholic acid (CDCA) is a hydrophobic primary bile acid.¹ It is formed from cholesterol in the liver via a multistep process catalyzed by the cytochrome P450 (CYP) isoforms CYP7A1, CYP8B1, and CYP27A1. CDCA is a farnesoid X receptor (FXR) agonist that binds to FXRs in a TR-FRET assay (EC50 = 13 µM) and induces FXR transactivation in a reporter assay.^2,3 It induces transcription of the gene encoding the Nrf2 target glutamate cysteine ligase (GCL) in primary hepatocytes and HepG2 cells when used at concentrations ranging from 25 to 100 µM.⁴ CDCA MaxSpec® standard is a quantitative grade standard of CDCA that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This CDCA MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

This information has been provided by Cayman Chemical

References

1. Urizar, N.L., Liverman, A.B., Dodds, D.T., et al. A natural product that lowers cholesterol as an antagonist ligand for FXR. Science 296(5573), 1703-1706 (2002).

2. Ohinata, Y., Payer, B., O'Carroll, D., et al. Blimp1 is a critical determinant of the germ cell lineage in mice. Nature 436(7048), 207-213 (2005).

3. Tan, K.P., Yang, M., and Ito, S. Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stress. Mol. Pharmacol. 72(5), 1380-1390 (2007).

4. Fiorucci, S., and Distrutti, E. Chenodeoxycholic acid: An update on its therapeutic applications. Bile acids and their receptors. Handbook of experimental pharmacology 256, 265-282 (2019).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Naturally Occurring Bile Acids and Alcohols and Their Origins,
The Bile Acids Chemistry, Physiology, and Metabolism, 1971

DOI: 10.1007/978-1-4757-0647-5

InChiKey (Click to copy)

RUDATBOHQWOJDD-BSWAIDMHSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])[C@H](O)C[C@]2([H])C[C@H](O)C1

Wikipedia

Chenodeoxycholic_acid

KEGG ID

C02528

HMDB ID

HMDB0000518

CHEBI ID

16755

LIPIDBANK ID

BBA0032