Structure Database (LMSD)

Common Name
Glycochenodeoxycholic acid
Systematic Name
N-(3α,7α-dihydroxy-5β-cholan-24-oyl)-glycine
Synonyms
  • Chenodeoxycholic acid glycine conjugate
  • Chenoglycodeoxycholic acid
  • GCDCA
LM ID
LMST05030008
Formula
Exact Mass
Calculate m/z
449.314124
Sum Composition
Status
Curated



Classification

Biological Context

Glycochenodeoxycholic acid (GCDCA) is a glycine-conjugated form of the primary bile acid chenodeoxycholic acid .1 It reduces formation of cholic acid in primary human hepatocytes when used at a concentration of 100 µM.2 GCDCA (50, 75, and 100 µM) reduces the number of LC3 puncta, a marker of autophagy, and is cytotoxic to L-02 hepatocytes.1 GCDCA (50 µM) induces apoptosis in isolated rat hepatocytes, an effect that can be blocked by the protein kinase C (PKC) inhibitor chelerythrine .3 Fecal levels of GCDCA are decreased in a rat model of high-fat diet-induced obesity compared with rats fed a normal diet.4 Glycochenodeoxycholic acid MaxSpec® standard is a quantitative grade standard of glycochenodeoxycholic acid 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. The verified concentration is provided on the certificate of analysis. This Glycochenodeoxycholic acid 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

3. Ellis, E., Axelson, M., Abrahamsson, A., et al. Feedback regulation of bile acid synthesis in primary human hepatocytes: Evidence that CDCA is the strongest inhibitor. Hepatology 38(4), 930-938 (2003).
4. Gonzalez, B., Fisher, C., and Rosser, B.G. Glycochenodeoxycholic acid (GCDC) induced hepatocyte apoptosis is associated with early modulation of intracellular PKC activity. Mol. Cell. Biochem. 207(1-2), 19-27 (2000).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Mechanism of cholestasis. 6. Bile acids in human livers with or without biliary obstruction.,
Gastroenterology, 1972
Pubmed ID: 6384004

String Representations

InChiKey (Click to copy)
GHCZAUBVMUEKKP-GYPHWSFCSA-N
InChi (Click to copy)
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1
SMILES (Click to copy)
[C@]12([C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCC(=O)NCC(=O)O)CC[C@@]21[H])[H]

Other Databases

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 458.59
Topological Polar Surface Area 106.86
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 6
logP 4.45
Molar Refractivity 123.17

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Created at
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Updated at
24th Apr 2024