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Structure Database (LMSD)

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Common Name

Isodeoxycholic acid

Systematic Name

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

Synonyms

EDCA
isoDCA
3-Epideoxycholic Acid

LM ID

LMST04010042

Formula

C₂₄H₄₀O₄

Exact Mass

Calculate m/z

392.29266

Sum Composition

ST 24:1;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

3-Epideoxycholic acid is a secondary bile acid formed via epimerization of deoxycholic acid (DCA) by gut microbiota.¹ It has reduced detergent activity and is less active than DCA in inhibiting growth in a panel of seven gut bacteria species. 3-Epideoxycholic acid (10 and 20 µM) increases the growth of Caco-2 colon cancer cells but to a lesser extent than DCA.² It increases the levels of Foxp3+CD4+ regulatory T cells (Tregs) in a co-culture of naïve T cells and dendritic cells.³

This information has been provided by Cayman Chemical

References

1. Devlin, A.S., and Fischbach, M.A. A biosynthetic pathway for a prominent class of microbiota-derived bile acids. Nat. Chem. Biol. 11(9), 685-690 (2018).

2. Campbell, C., McKenney, P.T., Konstantinovsky, D., et al. Bacterial metabolism of bile acids promotes generation of peripheral regulatory T cells. Nature 58(7809), 475-479 (2020).

3. Milovic, V., Teller, I.C., Faust, D., et al. Effects of deoxycholate on human colon cancer cells: Apoptosis or proliferation. Eur. J. Clin. Invest. 32(1), 29-34 (2002).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry.,
J Lipid Res, 1977

Pubmed ID: 864325

String Representations

InChiKey (Click to copy)

KXGVEGMKQFWNSR-OFYXWCICSA-N

InChi (Click to copy)

InChI=1S/C24H40O4/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/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21+,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])CC[C@]2([H])C[C@@H](O)C1