LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Isolithocholic acid

Systematic Name

3β-Hydroxy-5β-cholan-24-oic Acid

Synonyms

Isolithocholate
iso-LCA

LM ID

LMST04010004

Formula

C₂₄H₄₀O₃

Exact Mass

Calculate m/z

376.297745

Sum Composition

ST 24:1;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Isolithocholic acid is a bile acid that is formed via microbial metabolism of lithocholic acid (LCA) or lithocholic acid 3α-sulfate .^1,2 Isolithocholic acid (0.01%) inhibits spore germination induced by taurocholic acid (TCA) in the C. difficile strains CD196, M68, BI9, and 630, as well as inhibits growth and decreases the cytotoxicity of C. difficile culture supernatants to Vero cells when used at a concentration of 0.0003%.³ Fecal levels of isolithocholic acid are decreased in a rat model of high-fat diet-induced obesity compared with rats fed a normal diet.⁴

This information has been provided by Cayman Chemical

References

1. Borriello, S.P., and Owen, R.W. The metabolism of lithocholic acid and lithocholic acid-3-α-sulfate by human fecal bacteria. Lipids 17(7), 477-482 (1982).

2. Thanissery, R., Winston, J.A., and Theriot, C.M. Inhibition of spore germination, growth, and toxin activity of clinically relevant C. difficile strains by gut microbiota derived secondary bile acids. Anaerobe 45, 86-100 (2017).

3. Lin, H., An, Y., Tang, H., et al. Alterations of bile acids and gut microbiota in obesity induced by high fat diet in rat model. J. Agric. Food Chem. 67(13), 3624-3632 (2019).

4. Batta, A.K., Salen, G., and Shefer, S. Transformation of bile acids into iso-bile acids by Clostridium perfringes: Possible transport of 3β-hydrogen via the coenzyme. Hepatology 5(6), 1126-1131 (1985).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Clostridium (#1485)

Clostridia (#186801)

The metabolism of lithocholic acid and lithocholic acid-3-alpha-sulfate by human fecal bacteria.,
Lipids, 1982

Pubmed ID: 7121208

String Representations

InChiKey (Click to copy)

SMEROWZSTRWXGI-WFVDQZAMSA-N

InChi (Click to copy)

InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,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])CC[C@]2([H])C[C@@H](O)C1