LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Glycohyodeoxycholic acid

Systematic Name

N-(3α,6α-Dihydroxy-5β-cholan-24-oyl)-glycine

Synonyms

GHDCA
Glycine hyodeoxycholate

LM ID

LMST05030023

Formula

C₂₆H₄₃NO₅

Exact Mass

Calculate m/z

449.314124

Sum Composition

ST 24:1;O3;Gly

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

Classification

Biological Context

Glycohyodeoxycholic acid is a major metabolite of the secondary bile acid hyodeoxycholic acid in humans.¹ Glycohyodeoxycholic acid supplementation in prairie dogs fed a lithogenic diet decreases the frequency of cholesterol crystals in the gallbladder and inhibits the activity of cholesterol 7α-hydroxylase.²

This information has been provided by Cayman Chemical

References

1. McSherry, C.K., Mosbach, E.H., Cohen, B.I., et al. Hyodeoxycholic acid: A new approach to gallstone prevention. Am. J. Surg. 149(1), 126-132 (1985).

2. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Intestinal absorption, excretion, and biotransformation of hyodeoxycholic acid in man.,
J Lipid Res, 1983

Pubmed ID: 6875384

String Representations

InChiKey (Click to copy)

SPOIYSFQOFYOFZ-BRDORRHWSA-N

InChi (Click to copy)

InChI=1S/C26H43NO5/c1-15(4-7-23(30)27-14-24(31)32)18-5-6-19-17-13-22(29)21-12-16(28)8-10-26(21,3)20(17)9-11-25(18,19)2/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17+,18-,19+,20+,21+,22+,25-,26-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(NCC(=O)O)=O)CC[C@@]4([H])[C@]3([H])C[C@H](O)[C@]2([H])C[C@H](O)C1