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Structure Database (LMSD)

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Common Name

3-Oxocholic acid

Systematic Name

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

Synonyms

3-Dehydrocholic acid
3-ketoCA
3-Ketocholic acid

LM ID

LMST04010443

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

3-Oxocholic acid is a secondary bile acid and a metabolite of cholic acid in C. perfringens, a bacteria found in the intestines of mammals and in the environment.^1,2 3-Oxocholic acid serum levels increase following ileal transposition surgery in rats.³

This information has been provided by Cayman Chemical

References

1. Wahlström, A., Sayin, S.I., Marschall, H.-I., et al. Intestinal crosstalk between bile acids and microbiota and its impact on host metabolism. Cell Metab. 24(1), 41-50 (2016).

2. Macdonald, I.A., Forrest, T.P., Costain, G.A., et al. Identification of 7α-, 12α-dihydroxy-3-oxo cholanoic acid as the major degradation product from cholic by C. perfringens. J. Steroid Biochem. 9(4), 353-358 (1978).

3. Yan, K., Chen, W., Zhu, H., et al. The changes of serum metabolites in diabetic GK rats after ileal transposition surgery. Obes. Surg. 29(3), 882-890 (2019).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Clostridium perfringens (#1502)

Clostridia (#186801)

Identification of 7alpha-, 12alpha-dihydroxy-3-oxo cholanoic acid as the major degradation product from cholic by C. perfringens,
J Steroid Biochem, 1978

Pubmed ID: 207931

String Representations

InChiKey (Click to copy)

OEKUSRBIIZNLHZ-DJDNIQJZSA-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/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

SMILES (Click to copy)

[C@@]12([H])[C@H](O)C[C@]3([H])CC(=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]