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Structure Database (LMSD)

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Common Name

7-Ketodeoxycholic acid

Systematic Name

3α,12α-Dihydroxy-7-oxo-5β-cholan-24-oic Acid

Synonyms

7-ketoDCA
7-oxodeoxycholic acid

LM ID

LMST04010184

Formula

C₂₄H₃₈O₅

Exact Mass

Calculate m/z

406.271925

Sum Composition

ST 24:2;O5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

7-keto Deoxycholic acid is a metabolite of the primary bile acid cholic acid .^1,2 Fecal levels of 7-keto deoxycholic acid are elevated in rats fed a diet supplemented with cholic acid compared with rats fed a control diet or a diet supplemented with cholesterol .¹ Hepatic levels of 7-keto deoxycholic acid are elevated in a mouse model of ethanol-induced alcoholic liver disease.³

This information has been provided by Cayman Chemical

References

1. 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).

2. Hirano, S., Masuda, N., Oda, H., et al. Transformation of bile acids by Clostridium perfringens. Appl. Environ. Microbiol. 42(3), 394-399 (1981).

3. Charkoftaki, G., Tan, W.Y., Berrios-Carcamo, P., et al. Liver metabolomics identifies bile acid profile changes at early stages of alcoholic liver disease in mice. Chem. Biol. Interact. 360, 109931 (2022).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Urinary and fecal keto bile acids in liver cirrhosis.,
Clin Chim Acta, 1981

Pubmed ID: 7285341

String Representations

InChiKey (Click to copy)

RHCPKKNRWFXMAT-RRWYKFPJSA-N

InChi (Click to copy)

InChI=1S/C24H38O5/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/h13-18,20,22,25,27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,20+,22+,23+,24-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])C[C@H](O)[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