// Workers AI · dad joke modeWhat did glycocholic acid say? "I'm bitter".
(Redirected from Glycocholate)
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| Names | |
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| IUPAC name
N-(3α,7α,12α-Trihydroxy-5β-cholan-24-oyl)glycine | |
| Systematic IUPAC name
{(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-Trihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}acetic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.815 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C26H43NO6 | |
| Molar mass | 465.631 g·mol−1 |
| Melting point | 130 °C (266 °F; 403 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine.[1] Its anion is called glycocholate.
Metabolism
[edit]The enzyme choloylglycine hydrolase converts glycocholic acid, to cholic acid and glycine:[2]
In humans, the enzyme is an important component of the gut microbiome, where it metabolises many bile acids.[3][4]
Clinical significance
[edit]In a prospective study, positive associations were observed between prediagnostic plasma levels of seven conjugated bile acid metabolites, including glycocholic acid, and colon cancer risk.[5] These findings support experimental data suggesting that high circulating bile acids promote colon cancer risk.[5][6]
See also
[edit]References
[edit]- ↑ "Glycocholic Acid". MeSH.
- ↑ Rossocha M, Schultz-Heienbrok R, von Moeller H, Coleman JP, Saenger W (2005). "Conjugated bile acid hydrolase is a tetrameric N-terminal thiol hydrolase with specific recognition of its cholyl but not of its tauryl product". Biochemistry. 44 (15): 5739–48. doi:10.1021/bi0473206. PMID 15823032.
- ↑ Marchesini, María Inés; Connolly, Joseph; Delpino, María Victoria; Baldi, Pablo C.; Mujer, Cesar V.; Delvecchio, Vito G.; Comerci, Diego J. (2011). "Brucella abortus Choloylglycine Hydrolase Affects Cell Envelope Composition and Host Cell Internalization". PLOS ONE. 6 (12) e28480. doi:10.1371/journal.pone.0028480. PMC 3234258. PMID 22174816.
- ↑ Bracken, Amy K.; Malarney, Kien P.; Chang, Pamela V. (2026). "Chemical Proteomics Reveals Regulation of Bile Salt Hydrolases via Oxidative Post-translational Modifications". Journal of the American Chemical Society. 148 (5): 5378–5386. doi:10.1021/jacs.5c18912. PMC 12903841. PMID 41612134.
- 1 2 Kühn T, Stepien M, López-Nogueroles M, Damms-Machado A, Sookthai D, Johnson T, Roca M, Hüsing A, Maldonado SG, Cross AJ, Murphy N, Freisling H, Rinaldi S, Scalbert A, Fedirko V, Severi G, Boutron-Ruault MC, Mancini FR, Sowah SA, Boeing H, Jakszyn P, Sánchez MJ, Merino S, Colorado-Yohar S, Barricarte A, Khaw KT, Schmidt JA, Perez-Cornago A, Trichopoulou A, Karakatsani A, Thriskos P, Palli D, Agnoli C, Tumino R, Sacerdote C, Panico S, Bueno-de-Mesquita B, van Gils CH, Heath AK, Gunter MJ, Riboli E, Lahoz A, Jenab M, Kaaks R (May 2020). "Prediagnostic Plasma Bile Acid Levels and Colon Cancer Risk: A Prospective Study". J Natl Cancer Inst. 112 (5): 516–524. doi:10.1093/jnci/djz166. PMC 7225675. PMID 31435679.
- ↑ Bernstein H, Bernstein C (January 2023). "Bile acids as carcinogens in the colon and at other sites in the gastrointestinal system". Exp Biol Med (Maywood). 248 (1): 79–89. doi:10.1177/15353702221131858. PMC 9989147. PMID 36408538.