Structure Database (LMSD)

Common Name
Glycocholic Acid
Systematic Name
N-(3α,7α,12α-trihydroxy-5β-cholan-24-oyl)-glycine
Synonyms
  • Cholylglycine
  • GCA
LM ID
LMST05030001
Formula
Exact Mass
Calculate m/z
465.309039
Sum Composition
Status
Curated





Classification

Biological Context

Glycocholic acid is a glycine-conjugated form of the primary bile acid cholic acid and has roles in the emulsification of fats.1,2 It reduces expression of the gene encoding the farnesoid X receptor (FXR) and increases expression of the genes encoding the bile acid receptors TGR5 and S1PR2 in SNU-245 cells when used at a concentration of 1.6 μmol/ml.3 Glycocholic acid (250 μM) increases the intracellular accumulation and cytotoxicity of epirubicin in Caco-2 cells, as well as decreases expression of the genes encoding multidrug resistance protein 1 (MDR1), MDR-associated protein 1 (MRP1), and MRP2 when used alone or in combination with epirubicin.4 It increases absorption of epirubicin into everted sacs of rat ileum and jejunum when used at a concentration of 250 μM. The bile acid composition ratio of glycocholic acid is elevated in bile of patients with cholangiocarcinoma compared with patients with pancreatic cancer or benign biliary diseases.3 Serum levels of glycocholic acid are elevated in patients with hepatocellular carcinoma compared with healthy individuals.2

This information has been provided by Cayman Chemical

References

1. Lo, Y.L., Ho, C.T., and Tsai, F.L. Inhibit multidrug resistance and induce apoptosis by using glycocholic acid and epirubicin. Eur. J. Pharm. Sci. 35(1-2), 52-67 (2008).
2. Song, W.-S., Park, H.-M., Ha, J.M., et al. Discovery of glycocholic acid and taurochenodeoxycholic acid as phenotypic biomarkers in cholangiocarcinoma. Sci. Rep. 8(1), 11088 (2018).
3. Guo, C., Xie, C., Ding, P., et al. Quantification of glycocholic acid in human serum by stable isotope dilution ultra performance liquid chromatography electrospray ionization tandem mass spectrometry. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1072, 315-319 (2018).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
The capacity of human liver homogenates to synthesize taurocholic and glycocholic acid in vitro.,
Scand J Clin Lab Invest, 1966
Pubmed ID: 5959320

String Representations

InChiKey (Click to copy)
RFDAIACWWDREDC-FRVQLJSFSA-N
InChi (Click to copy)
InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,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])C[C@H](O)[C@]1(C)[C@@]([H])([C@@](C)([H])CCC(NCC(O)=O)=O)CC[C@@]21[H])[H]

Other Databases

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

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 467.38
Topological Polar Surface Area 127.09
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 7
logP 3.71
Molar Refractivity 125.07

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Created at
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Updated at
24th Apr 2024