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Structure Database (LMSD)

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Common Name

alpha-muricholic acid

Systematic Name

3α,6β,7α-Trihydroxy-5β-cholan-24-oic Acid

Synonyms

alpha-MCA

LM ID

LMST04010066

Formula

C₂₄H₄₀O₅

Exact Mass

Calculate m/z

408.287575

Sum Composition

ST 24:1;O5

Status

Curated

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Classification

Biological Context

α-Muricholic acid is a murine-specific primary bile acid.^1,2 Dietary administration of soybean protein decreases fecal levels of α-muricholic acid in mice with high-fat diet-induced obesity which correlates with increases in fecal Clostridium cluster XIVa, a major producer of secondary bile acids.³ Plasma, liver, and muscle levels of α-muricholic acid are increased in mice switched from a high-fat to low-fat diet.⁴

This information has been provided by Cayman Chemical

References

1. La Frano, M.R., Hernandez-Carretero, A., Weber, N., et al. Diet-induced obesity and weight loss alter bile acid concentrations and bile acid-sensitive gene expression in insulin target tissues of C57BL/6J mice. Nutr. Res. 46, 11-21 (2017).

2. Watanabe, K., Igarashi, M., Li, X., et al. Dietary soybean protein ameliorates high-fat diet-induced obesity by modifying the gut microbiota-dependent biotransformation of bile acids. PLoS One 13(8), e0202083 (2018).

3. Eyssen, H.J., Parmentier, G.G., and Mertens, J.A. Sulfate bile acids in germ-free and conventional mice. Eur. J. Biochem. 66(3), 507-514 (1976).

4. Uehara, T., Xi Peng, X., Bennett, B., et al. c-Jun N-terminal kinase mediates hepatic injury after rat liver transplantation. Transplantation 78(3), 324-332 (2004).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Bile acid synthesis in young and old rats.,
Arch Gerontol Geriatr, 1996

Pubmed ID: 15374163

String Representations

InChiKey (Click to copy)

DKPMWHFRUGMUKF-GDYCBZMLSA-N

InChi (Click to copy)

InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,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@@H](O)[C@]2([H])C[C@H](O)C1