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Structure Database (LMSD)

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Common Name

Isoursodeoxycholic acid

Systematic Name

3β,7β-Dihydroxy-5β-cholan-24-oic Acid

Synonyms

isoUDCA
IUDCA
3beta-Ursodeoxycholic Acid
beta-UDCA

LM ID

LMST04010035

Formula

C₂₄H₄₀O₄

Exact Mass

Calculate m/z

392.29266

Sum Composition

ST 24:1;O4

Status

Curated

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Classification

Biological Context

Isoursodeoxycholic acid is a 3β-epimer of the secondary bile acid ursodeoxycholic acid (UDCA).¹ It is formed from UDCA via epimerization in vivo and can be isomerized back into UDCA.^2,1 Isoursodeoxycholic acid (2,500 mg/kg in the diet) decreases serum alkaline phosphatase (ALP), aspartate aminotransferase (AST), and alanine transaminase (ALT) levels in bile duct-ligated rats but does not affect liver histology.³

This information has been provided by Cayman Chemical

References

1. Purucker, E., Marschall, H.-U., Winograd, R., et al. Metabolism and effects on cholestasis of isoursodeoxycholic and ursodeoxycholic acids in bile duct ligated rats. Biochim. Biophys. Acta 1526(1), 44-52 (2001).

2. Beuers, U., Fischer, S., Spengler, U., et al. Formation of iso-ursodeoxycholic acid during administration of ursodeoxycholic acid in man. J. Hepatol. 13(1), 97-103 (1991).

3. Marschall, H.-U., Broomé, U., Einarsson, C., et al. Isoursodeoxycholic acid: Metabolism and therapeutic effects in primary biliary cirrhosis. J. Lipid Res. 42(5), 735-742 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Formation of iso-ursodeoxycholic acid during administration of ursodeoxycholic acid in man.,
J Hepatol, 1991

Pubmed ID: 1918882

String Representations

InChiKey (Click to copy)

RUDATBOHQWOJDD-DNMBCGTGSA-N

InChi (Click to copy)

InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,22+,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@@H](O)C[C@]2([H])C[C@@H](O)C1