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Structure Database (LMSD)

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Common Name

Nordeoxycholic acid

Systematic Name

24-nor-3α,12α-dihydroxy-5β-cholan-23-oic acid

Synonyms

23-norDCA
23-Nordeoxycholic acid
23-NDCA

LM ID

LMST04060020

Formula

C₂₃H₃₈O₄

Exact Mass

Calculate m/z

378.27701

Sum Composition

ST 23:1;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Nordeoxycholic acid is a metabolite of the bile acid norcholic acid and a 23-carbon derivative of deoxycholic acid .¹ Levels of nordeoxycholic acid are decreased in the liver of rats in a high-fat diet model of non-alcoholic fatty liver disease (NAFLD) and serum levels are lower in men compared with women.^2,3 Nordeoxycholic acid has commonly been used as an internal standard for the quantification of bile acids in various sample types by GC- and LC-MS.^4,5

This information has been provided by Cayman Chemical

References

1. Tang, Y., Zhang, J., Li, J., et al. Turnover of bile acids in liver, serum and caecal content by high-fat diet feeding affects hepatic steatosis in rats. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1864(10), 1293-1304 (2019).

2. Nakatomi, F., Kihira, K., Kuramoto, T., et al. Intestinal absorption and metabolism of norcholic acid in rats. J. Pharmacobiodyn 8(7), 557-563 (1985).

3. Xie, G., Wang, Y., Wang, X., et al. Profiling of serum bile acids in a healthy Chinese population using UPLC-MS/MS. J. Proteome Res. 14(2), 850-859 (2015).

4. Bergeron, A., Furtado, M., and Garofolo, F. Importance of using highly pure internal standards for successful liquid chromatography/tandem mass spectrometric bioanalytical assays. Rapid Commun. Mass Spectrom. 23(9), 1287-1197 (2009).

5. Evrard, E., and Janssen, G. Gas-liquid chromatographic determination of human fecal bile acids. J. Lipid Res. 9(2), 226-236 (1968).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Turnover of bile acids in liver, serum and caecal content by high-fat diet feeding affects hepatic steatosis in rats.,
Biochim Biophys Acta Mol Cell Biol Lipids, 2019

Pubmed ID: 31170503

String Representations

InChiKey (Click to copy)

PLRQOCVIINWCFA-AHFDLSHQSA-N

InChi (Click to copy)

InChI=1S/C23H38O4/c1-13(10-21(26)27)17-6-7-18-16-5-4-14-11-15(24)8-9-22(14,2)19(16)12-20(25)23(17,18)3/h13-20,24-25H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17-,18+,19+,20+,22+,23-/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)CC(=O)O)CC[C@@]4([H])[C@]3([H])CC[C@]2([H])C[C@H](O)C1