Glycochenodeoxycholic acid

Glycochenodeoxycholic acid
Names
	IUPAC name N-(3α,7α-Dihydroxy-5β-cholan-24-oyl)glycine
	Systematic IUPAC name {(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}acetic acid
Identifiers
CAS Number	640-79-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	12027 ;
IUPHAR/BPS	4545;
PubChem CID	12544;
UNII	451ZNJ667Y ;
CompTox Dashboard (EPA)	DTXSID301020165 ;
	InChI 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 Key: GHCZAUBVMUEKKP-GYPHWSFCSA-N ;
	SMILES C[C@H](CCC(=O)NCC(=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;
Properties
Chemical formula	C26H43NO5
Molar mass	449.62 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Glycochenodeoxycholic acid is a bile salt formed in the liver from chenodeoxycholic acid and glycine, usually found as the sodium salt.^[1]^[2] It acts as a detergent to solubilize fats for absorption.^{[citation needed]}

Positive associations were observed between prediagnostic plasma levels of seven different conjugated bile acid metabolites, including glycochenodeoxycholic acid, and colon cancer risk.^[3] These findings support experimental data suggesting that a high bile acid load promotes colon cancer.^[3]^[4]

References

^ Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). "DrugBank 3.0: a comprehensive resource for omics research on drugs". Nucleic Acids Res. 39 (Database issue): D1035–41. doi:10.1093/nar/gkq1126. PMC 3013709. PMID 21059682.
^ Wishart DS; Knox C; Guo AC; Cheng D; Shrivastava S; Tzur D; Gautam B; Hassanali M (2008). "DrugBank: a knowledgebase for drugs, drug actions and drug targets". Nucleic Acids Research. 36 (Database issue): D901–6. doi:10.1093/nar/gkm958. PMC 2238889. PMID 18048412.
^ ^a ^b 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.

This article about a steroid is a stub. You can help Wikipedia by expanding it.

[1] Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). "DrugBank 3.0: a comprehensive resource for omics research on drugs". Nucleic Acids Res. 39 (Database issue): D1035–41. doi:10.1093/nar/gkq1126. PMC 3013709. PMID 21059682.

[2] Wishart DS; Knox C; Guo AC; Cheng D; Shrivastava S; Tzur D; Gautam B; Hassanali M (2008). "DrugBank: a knowledgebase for drugs, drug actions and drug targets". Nucleic Acids Research. 36 (Database issue): D901–6. doi:10.1093/nar/gkm958. PMC 2238889. PMID 18048412.

[Kuhn2020-3] 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.

[4] 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.

[1]

[2]

[3]

[4]