Structure Database (LMSD)

Common Name
Taurolithocholic acid
Systematic Name
N-(3α-hydroxy-5β-cholan-24-oyl)-taurine
Synonyms
  • Taurolithocholate
  • TLCA
LM ID
LMST05040003
Formula
Exact Mass
Calculate m/z
483.301846
Sum Composition
Status
Curated


Classification

Biological Context

Taurolithocholic acid (TLCA) is a taurine-conjugated form of the secondary bile acid lithocholic acid .1 TLCA (75 μM) increases caspase-3 and -7 activity in Hep3B cells transfected with sodium taurocholate cotransporting peptide (NTCP), but not nontransfected Hep3B cells.2 It has been used to induce cholestasis in ex vivo and in vivo animal models of hepatocellular cholestasis.3,4 Serum levels of TLCA increase approximately 5-fold within two hours during an oral lipid tolerance test in humans.1 TLCA MaxSpec® standard is a quantitative grade standard of TLCA that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. The verified concentration is provided on the certificate of analysis. This TLCA MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

This information has been provided by Cayman Chemical

References

2. Rust, C., Wild, N., Bernt, C., et al. Bile acid-induced apoptosis in hepatocytes is caspase-6-dependent. The Journal of Biological Chemisty 284(5), 2908-2916 (2009).
3. Schmid, A., Neumann, H., Karrasch, T., et al. Bile acid metabolome after an oral lipid tolerance test by liquid chromatography-tandem mass spectrometry (LC-MS/MS). PLoS One 11(2), e0148869 (2016).

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)
QBYUNVOYXHFVKC-GBURMNQMSA-N
InChi (Click to copy)
InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1
SMILES (Click to copy)
[C@@]12([H])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](O)C[C@@]3([H])CC[C@@]21[H]

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 479.74
Topological Polar Surface Area 103.70
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 6.53
Molar Refractivity 130.45

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Created at
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Updated at
24th Apr 2024