LIPID MAPS

Structure Database (LMSD)

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

Hyodeoxycholic acid

Systematic Name

3α,6α-Dihydroxy-5β-cholan-24-oic Acid

Synonyms

HDCA
alpha-Hyodeoxycholic Acid

LM ID

LMST04010024

Formula

C₂₄H₄₀O₄

Exact Mass

Calculate m/z

392.292661

Sum Composition

ST 24:1;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

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

Classification

Biological Context

Hyodeoxycholic acid (HDCA) is a secondary bile acid.¹ It is produced from lithocholic acid by gut bacteria.^1,2,3 Dietary administration of HDCA (1.25% w/w) decreases plasma VLDL and LDL cholesterol levels and reduces fasting glucose levels and atherosclerotic lesion size in LDL receptor knockout mice fed a Western diet.⁴ Serum levels of HDCA are increased in patients with Crohn’s disease or ulcerative colitis.⁵

This information has been provided by Cayman Chemical

References

1. Sacquet, E., Parquet, M., Riottot, M., et al. Intestinal absorption, excretion, and biotransformation of hyodeoxycholic acid in man. J. Lipid. Res. 24(5), 604-613 (1983).

2. Shih, D.M., Shaposhnik, Z., Meng, Y., et al. Hyodeoxycholic acid improves HDL function and inhibits atherosclerotic lesion formation in LDLR-knockout mice. FASEB J. 27(9), 3805-3817 (2013).

3. Madsen, D., Beaver, M., Chang, L., et al. Analysis of bile acids in conventional and germfree rats. J. Lipid. Res. 17(2), 107-111 (1976).

4. Gnewuch, C., Liebisch, G., Langmann, T., et al. Serum bile acid profiling reflects enterohepatic detoxification state and intestinal barrier function in inflammatory bowel disease. World J. Gastroenterol. 15(25), 3134-3141 (2009).

5. Einarsson, K. On the formation of hyodeoxycholic acid in the rat. Bile acids and steroids 154. J. Biol. Chem. 241(3), 534-539 (1966).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man.,
Biochem J, 1976

Pubmed ID: 938463

DOI: 10.1042/bj1540507

String Representations

InChiKey (Click to copy)

DGABKXLVXPYZII-SIBKNCMHSA-N

InChi (Click to copy)

InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/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])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])C[C@H](O)[C@]2([H])C[C@H](O)C1