LIPID MAPS

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

378.277011

Sum Composition

ST 23:1;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

No other lipid differing only in stereochemistry/bond geometry found

View studies deposited in Metabolomics Workbench in which this molecule has been identified

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

2. 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).

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

DOI: 10.1016/j.bbalip.2019.05.016

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