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Structure Database (LMSD)

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Common Name

beta-muricholic acid

Systematic Name

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

Synonyms

beta-MCA

LM ID

LMST04010067

Formula

C₂₄H₄₀O₅

Exact Mass

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408.287575

Sum Composition

ST 24:1;O5

Status

Curated

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Classification

Biological Context

β-Muricholic acid (β-MCA) is a murine-specific primary bile acid.^1,2 Dietary administration of β-MCA reduces HMG-CoA reductase activity in liver microsomes from mice fed a high cholesterol and cholic acid diet.³ Dietary administration of β-MCA also dissolves 100% of gallstones in a gallstone-susceptible mouse model of diet-induced cholesterol gallstones.⁴

This information has been provided by Cayman Chemical

References

1. 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).

2. Fujino, Y., Nakayama, K., Yoshimura, K., et al. Suppression of hepatic HMG-CoA reductase activity by β-muricholic acid in mice fed a diet containing cholesterol and cholic acid. Jpn. J. Pharmacol. 46(4), 421-423 (1988).

3. Wang, D.Q.-H., and Tazuma, S. Effect of β-muricholic acid on the prevention and dissolution of cholesterol gallstones in C57L/J mice. J. Lipid. Res. 43(11), 1960-1968 (2002).

4. Wahlström, A., Sayin, S.I., Marschall, H.-I., et al. Intestinal crosstalk between bile acids and microbiota and its impact on host metabolism. Cell Metab. 24(1), 41-50 (2016).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Delta 22-beta-muricholic acid in monoassociated rats and conventional rats.,
Lipids, 1994

Pubmed ID: 8177022

String Representations

InChiKey (Click to copy)

DKPMWHFRUGMUKF-CRKPLTDNSA-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