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Structure Database (LMSD)

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Common Name

Taurolithocholate sulfate

Systematic Name

N-(3α-hydroxy-5β-cholan-24-oyl)-taurine 3-sulfate

Synonyms

3-Sulfotaurolithocholic acid
3S-TLCA
TLCA3S
TLC-S

LM ID

LMST05020003

Formula

C₂₆H₄₅NO₈S₂

Exact Mass

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563.258663

Status

Curated

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Classification

Biological Context

Taurolithocholic acid 3-sulfate (TLCA3S) is a metabolite of the conjugated bile acid taurolithocholic acid .¹ TLCA3S has been used to study bile acid transport in cellular models and to induce pancreatitis in mouse models of bile acid infusion pancreatitis.^2,3

This information has been provided by Cayman Chemical

References

1. Blazquez, A.G., Briz, O., Romero, M.R., et al. Characterization of the role of ABCG2 as a bile acid transporter in liver and placenta. Mol. Pharmacol. 81(2), 273-283 (2012).

2. Muili, K.A., Wang, D., Orabi, A.I., et al. Bile acids induce pancreatic acinar cell injury and pancreatitis by activating calcineurin. The Journal of Biological Chemisty 288(1), 570-580 (2013).

3. Lefebvre, P., Cariou, B., Lien, F., et al. Role of bile acids and bile acid receptors in metabolic regulation. Physiol. Rev. 89(1), 147-191 (2009).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Bile acid sulfates. I. Synthesis of lithocholic acid sulfates and their identification in human bile.,
J Lipid Res, 1971

Pubmed ID: 5124532

String Representations

InChiKey (Click to copy)

HSNPMXROZIQAQD-GBURMNQMSA-N

InChi (Click to copy)

InChI=1S/C26H45NO8S2/c1-17(4-9-24(28)27-14-15-36(29,30)31)21-7-8-22-20-6-5-18-16-19(35-37(32,33)34)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23H,4-16H2,1-3H3,(H,27,28)(H,29,30,31)(H,32,33,34)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

SMILES (Click to copy)

[C@]12(CC[C@]([H])([C@H](C)CCC(=O)NCCS(=O)(=O)O)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@@H](OS(=O)(O)=O)C[C@@]3([H])CC[C@]12[H])[H]