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Structure Database (LMSD)

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Common Name

Glycoursodeoxycholic acid

Systematic Name

N-(3α,7β-dihydroxy-5β-cholan-24-oyl)-glycine

Synonyms

Glycoursodeoxycholate
Ursodeoxycholylglycine
GUDCA

LM ID

LMST05030016

Formula

C₂₆H₄₃NO₅

Exact Mass

Calculate m/z

449.314124

Sum Composition

ST 24:1;O3;Gly

Status

Curated

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Classification

Biological Context

Glycoursodeoxycholic acid (GUDCA) is a glycine-conjugated form of the secondary bile acid ursodeoxycholic acid (UDCA).^1,2 It has antioxidant effects in vitro in Barrett’s esophagus cells and primary cultured rat neurons.^3,4 GUDCA reduces the levels of inflammatory cytokines and prevents cell death induced by unconjugated bilirubin in an astroglial cell model of neonatal hyperbilirubinemia.⁵ Oral administration of GUDCA (500 mg/kg per day) decreases the severity of symptoms and increases the amount of A. muciniphila, a bacterial species commonly decreased in patients with inflammatory bowel disease (IBD), in a mouse model of colitis.²

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. Van den Bossche, L., Hindryckx, P., Devisscher, L., et al. Ursodeoxycholic acid and its taurine- or glycine-conjugated species reduce colitogenic dysbiosis and equally suppress experimental colitis in mice. Appl. Environ. Microbiol. 83(7), e02766-02716 (2017).

3. Goldman, A., Condon, A., Adler, E., et al. Protective effects of glycoursodeoxycholic acid in Barrett’s esophagus cells. Dis. Esophagus 23(2), 83-93 (2010).

4. Fernandes, A., Vaz, A.R., Falcao, A.S., et al. Glycoursodeoxycholic acid and interleukin-10 modulate the reactivity of rat cortical astrocytes to unconjugated bilirubin. J. Neuropathol. Exp. Neurol. 66(9), 789-798 (2007).

5. Brito, M.A., Lima, S., Fernandes, A., et al. Bilirubin injury to neurons: Contribution of oxidative stress and rescue by glycoursodeoxycholic acid. Neurotoxicology 29(2), 259-269 (2008).

String Representations

InChiKey (Click to copy)

GHCZAUBVMUEKKP-XROMFQGDSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

O[C@H]1C[C@@]2([H])C[C@H](O)[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