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Structure Database (LMSD)

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Common Name

7-oxolithocholic acid

Systematic Name

3α-Hydroxy-7-oxo-5β-cholan-24-oic Acid

Synonyms

7-Ketolithocholic acid
7-ketoLCA

LM ID

LMST04010150

Formula

C₂₄H₃₈O₄

Exact Mass

Calculate m/z

390.27701

Sum Composition

ST 24:2;O4

Status

Curated

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Classification

Biological Context

7-keto Lithocholic acid is an intermediate in the synthesis of the secondary bile acid ursodeoxycholic acid by intestinal bacteria in humans.^1,2 It is formed from chenodeoxycholic acid in B. intestinalis isolated from human feces.¹ Venous infusion of 7-keto lithocholic acid (1.2 µmol/min per 100 g body weight) increases the bile flow rate and the concentration of bile bicarbonate in rats.³ 7-keto Lithocholic acid levels are decreased in rat feces in a model of adenine-induced chronic renal failure.⁴ Fecal levels are also reduced in patients with liver cirrhosis or hepatocellular carcinoma.⁵

This information has been provided by Cayman Chemical

References

1. Fukiya, S., Arata, M., Kawashima, H., et al. Conversion of cholic acid and chenodeoxycholic acid into their 7-oxo derivatives by Bacteroides intestinalis AM-1 isolated from human feces. FEMS Microbiol. Lett. 293(2), 263-270 (2009).

2. Fromm, H., Carlson, G.L., Hofmann, A.F., et al. Metabolism in man of 7-ketolithocholic acid: Precursor of cheno- and ursodeoxycholic acids. Am. J. Physiol. 239(3), G161-G166 (1980).

3. Kanai, S., Sato, Y., Nokubo, M., et al. Hepatic biotransformation and choleretic effect of 7-ketolithocholic acid in the rat. Lipids 24(10), 859–865 (1989).

4. Zhao, Y.Y., Cheng, X.L., Wei, F., et al. Application of faecal metabonomics on an experimental model of tubulointerstitial fibrosis by ultra performance liquid chromatography/high-sensitivity mass spectrometry with MSE data collection technique. Biomarkers 17(8), 721-729 (2012).

5. Cao, H., Huang, H., Xu, W., et al. Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal. Chim. Acta. 691(1-2), 68-75 (2011).

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)

DXOCDBGWDZAYRQ-AURDAFMXSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

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