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Structure Database (LMSD)

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Common Name

Glycolithocholic Acid

Systematic Name

N-[(3α,5β)-3-hydroxy-24-oxocholan-24-yl]-glycine

Synonyms

Lithocholic acid glycine conjugate
GLCA
Lithocholylglycine

LM ID

LMST05030009

Formula

C₂₆H₄₃NO₄

Exact Mass

Calculate m/z

433.319209

Sum Composition

ST 24:1;O2;Gly

Status

Curated

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Classification

Biological Context

Glycolithocholic acid is a glycine-conjugated form of the secondary bile acid lithocholic acid .¹ It is increased in the liver of mice fed a diet supplemented with ursodeoxycholic acid .² Glycolithocholic acid levels are decreased in the plasma following subcutaneous administration of PEG-obestatin(Cys10, Cys13), a modified peptide hormone, in lean or diet-induced obese mice.³ Serum glycolithocholic acid levels increase with age in children.⁴

This information has been provided by Cayman Chemical

References

1. Lefebvre, P., Cariou, B., Lien, F., et al. Role of bile acids and bile acid receptors in metabolic regulation. Physiol. Rev. 89(1), 147-191 (2009).

2. Semba, R.D., Gonzalez-Freier, M., Moaddel, R., et al. Environmental enteric dysfunction is associated with altered bile acid metabolism. J. Pediatr. Gastenterol. Nutr. 64(4), 536-540 (2017).

3. Cowan, E., Kimar, P., Burch, K.J., et al. Treatment of lean and diet-induced obesity (DIO) mice with a novel stable obestatin analogue alters plasma metabolite levels as detected by untargeted LC-MS metabolomics. Metabolomics 12(124), (2016).

4. Zhang, Y., and Klaassen, C.D. Effects of feeding bile acids and a bile acid sequestrant on hepatic bile acid composition in mice. J. Lipid Res. 51(11), 3230-3242 (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

METABOLITES OF LITHOCHOLIC ACID-24-C-14 IN HUMAN BILE AND FECES.,
J Lab Clin Med, 1964

Pubmed ID: 14179134

String Representations

InChiKey (Click to copy)

XBSQTYHEGZTYJE-OETIFKLTSA-N

InChi (Click to copy)

InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

SMILES (Click to copy)

O[C@H]1C[C@@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@@](C)([H])CCC(=O)NCC(=O)O)[C@@]4(C)CC[C@]3([H])[C@@]2(C)CC1