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Structure Database (LMSD)

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Common Name

Tauro-omega-muricholic acid

Systematic Name

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

Synonyms

TOMCA
T-omega-MCA

LM ID

LMST04010473

Formula

C₂₆H₄₅NO₇S

Exact Mass

Calculate m/z

515.291676

Sum Composition

ST 24:1;O4;Tau

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Tauro-ω-muricholic acid is a taurine-conjugated form of the secondary bile acid ω-muricholic acid . Hepatic levels of tauro-ω-muricholic acid are decreased in mice following a diet supplemented with cholic, deoxycholic, chenodeoxycholic, or ursodeoxycholic acid and in a high-fat diet-induced mouse model of non-alcoholic fatty liver disease (NAFLD).^1,2 Tauro-ω-muricholic acid is the predominant rare bile acid found in the serum of infants with early-onset neonatal sepsis.³

This information has been provided by Cayman Chemical

References

1. Zöhrer, E., Meinel, K., Fauler, G., et al. Neonatal sepsis leads to early rise of rare serum bile acid tauro-omega-muricholic acid (TOMCA). Pediatr. Res. 84(1), 66-70 (2018).

2. Tang, Y., Zhang, J., Li, J., et al. Turnover of bile acids in liver, serum and caecal content by high-fat diet feeding affects hepatic steatosis in rats. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1864(10), 1293-1304 (2019).

3. Zhang, Y., and Klaassen, C.D. Effects of feeding bile acids and a bile acid sequestrant on hepatic bile acid composition in mice. J. Lipid Res. 51(11), 3230-3242 (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Neonatal sepsis leads to early rise of rare serum bile acid tauro-omega-muricholic acid (TOMCA).,
Pediatr Res, 2018

Pubmed ID: 29795204

String Representations

InChiKey (Click to copy)

XSOLDPYUICCHJX-SYCKBGHMSA-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