LIPID MAPS

Cholic acid is a primary bile acid.¹ It is formed from cholesterol via a multistep process catalyzed by the cytochrome P450 (CYP) isoforms CYP7A1, CYP8B1, and CYP27A1. Cholic acid is conjugated to glycine or taurine by bile acid-CoA:amino acid N-acyltransferase (BAAT) to produce glycocholic acid (GCA) and taurocholic acid (TCA), respectively, in the liver, and is transformed into the secondary bile acid deoxycholic acid (DCA) by intestinal microbiota.^1,2,3 It induces C. difficile colony formation in an agar dilution assay when used at a concentration of 0.1% w/v.⁴ Dietary administration of cholic acid (0.4% w/w) increases serum cholesterol levels, biliary phospholipid secretion, and fecal DCA levels in rats.⁵

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References

1. Šarenac, T.M., and Mikov, M. Bile acid synthesis: From nature to the chemical modification and synthesis and their applications as drugs and nutrients. Front. Pharmacol. 9, 939 (2018).

2. Hunt, M.C., Siponen, M.I., and Alexson, S.E.H. The emerging role of acyl-CoA thioesterases and acyltransferases in regulating peroxisomal lipid metabolism. Biochim. Biophys. Acta 1822(9), 1397-1410 (2012).

3. Staley, C., Weingarden, A.R., Khoruts, A., et al. Interaction of gut microbiota with bile acid metabolism and its influence on disease states. Appl. Microbiol. Biotechnol. 101(1), 47-64 (2017).

4. Sorg, J.A., and Sonenshein, A.L. Bile salts and glycine as cogerminants for Clostridium difficile spores. J. Bacteriol. 190(7), 2505-2512 (2008).

5. Uchida, K., Nomura, Y., and Takeuchi, N. Effects of cholic acid, chenodeoxycholic acid, and their related bile acids on cholesterol, phospholipid, and bile acid levels in serum, liver, bile, and feces of rats. J. Biochem. 87(1), 187-194 (1980).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

The structure of sodium 3α,7α,12α-trihydroxy-5β-cholan-24-oate monohydrate (sodium cholate monohydrate),
Acta Cryst B, 1980

DOI: 10.1107/S056774088000310X

String Representations

InChiKey (Click to copy)

BHQCQFFYRZLCQQ-OELDTZBJSA-N

InChi (Click to copy)

InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/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(O)=O)CC[C@@]21[H])[H]