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
3D model of Taurolithocholic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
Admin
Created at
-
Updated at
24th Apr 2024