LIPID MAPS

Structure Database (LMSD)

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Common Name

Tauro-alpha-muricholic acid

Systematic Name

N-(3α,6β,7α-Trihydroxy-5β-cholan-24-oyl)-taurine

Synonyms

T-alpha-MCA

LM ID

LMST05040027

Formula

C₂₆H₄₅NO₇S

Exact Mass

Calculate m/z

515.291675

Sum Composition

ST 24:1;O4;Tau

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Biological Context

Tauro-α-muricholic acid (TαMCA) is an antagonist of the farnesoid X receptor (FXR; IC50 = 28 µM) and a taurine-conjugated form of the murine-specific primary bile acid α-muricholic acid .¹ TαMCA is common in rodents but has also been found in small amounts in human serum.²

This information has been provided by Cayman Chemical

References

1. Sayin, S.I., Wahlström, A., Felin, J., et al. Gut microbiota regulates bile acid metabolism by reducing the levels of tauro-beta-muricholic acid, a naturally occurring FXR antagonist. Cell Metab. 17(2), 225-235 (2013).

2. García-Cañaveras, J.C., Donato, M.T., Castell, J.V., et al. Targeted profiling of circulating and hepatic bile acids in human, mouse, and rat using a UPLC-MRM-MS-validated method. J. Lipid Res. 53(10), 2231-2241 (2012).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Targeted profiling of circulating and hepatic bile acids in human, mouse, and rat using a UPLC-MRM-MS-validated method.,
J Lipid Res, 2012

Pubmed ID: 22822028

String Representations

InChiKey (Click to copy)

XSOLDPYUICCHJX-QQXJNSDFSA-N

InChi (Click to copy)

InChI=1S/C26H45NO7S/c1-15(4-7-21(29)27-12-13-35(32,33)34)17-5-6-18-22-19(9-11-25(17,18)2)26(3)10-8-16(28)14-20(26)23(30)24(22)31/h15-20,22-24,28,30-31H,4-14H2,1-3H3,(H,27,29)(H,32,33,34)/t15-,16-,17-,18+,19+,20+,22+,23+,24+,25-,26-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(NCCS(O)(=O)=O)=O)CC[C@@]4([H])[C@]3([H])[C@H](O)[C@@H](O)[C@]2([H])C[C@H](O)C1