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Structure Database (LMSD)

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Common Name

12-Ketolithocholic acid

Systematic Name

3α-Hydroxy-12-oxo-5β-cholan-24-oic Acid

Synonyms

12-Oxolithocholic acid
12-Keto-LCA
12-KLCA

LM ID

LMST04010155

Formula

C₂₄H₃₈O₄

Exact Mass

Calculate m/z

390.27701

Sum Composition

ST 24:2;O4

Status

Curated

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Classification

Biological Context

12-keto Lithocholic acid is a metabolite of the secondary bile acid deoxycholic acid (DCA).^1,2 Fecal levels of 12-keto lithocholic acid are elevated in rats fed a diet supplemented with cholic acid or DCA compared with rats fed a control diet or a diet supplemented with cholesterol , hyodeoxycholic acid (HDCA), or lithocholic acid (LCA).² 12-keto Lithocholic acid activates the human pregnane X receptor (PXR; EC50 = 31.3 μM in a cell-based transactivation assay).³ 12-keto Lithocholic acid levels are increased in duodenal bile from patients with type 2 diabetes.⁴

This information has been provided by Cayman Chemical

References

1. Andersén, E., Karlaganis, G., and Sjövall, J. Altered bile acid profiles in duodenal bile and urine in diabetic subjects. Eur. J. Clin. Invest. 18(2), 166-172 (1988).

2. Krasowski, M.D., Yasuda, K., Hagey, L.R., et al. Evolution of the pregnane X receptor: Adaptation to cross-species differences in biliary bile salts. Mol. Endocrinol. 19(7), 1720-1739 (2005).

3. Sakai, K., Makino, T., Kawai, Y., et al. Intestinal microflora and bile acids. Effect of bile acids on the distribution of microflora and bile acid in the digestive tract of the rat. Microbiol. Immunol. 24(3), 187-196 (1980).

4. Franco, P., Porru, E., Fiori, J., et al. Identification and quantification of oxo-bile acids in human faeces with liquid chromatography-mass spectrometry: A potent tool for human gut acidic sterolbiome studies. J. Chromatogr. A. 1585, 70-81 (2019).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Simultaneous determination of keto and non-keto bile acids in human serum by gas chromatography with selected ion monitoring.,
J Chromatogr, 1990

Pubmed ID: 2338448

String Representations

InChiKey (Click to copy)

CVNYHSDFZXHMMJ-VPUMZWJWSA-N

InChi (Click to copy)

InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC(=O)[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])CC[C@]2([H])C[C@H](O)C1