Structure Database (LMSD)
Common Name
Taurochenodeoxycholic acid
Systematic Name
N-(3α,7α-dihydroxy-5β-cholan-24-oyl)-taurine
Synonyms
- Taurochenodeoxycholate
- 2-[(3a,7a-dihydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonate
- TCDCA
LM ID
LMST05040005
Formula
Exact Mass
Calculate m/z
499.296761
Sum Composition
Status
Curated
3D model of Taurochenodeoxycholic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Taurochenodeoxycholic acid (TCDCA) is a taurine-conjugated form of the primary bile acid chenodeoxycholic acid (CDCA).1 Serum levels of TCDCA increase approximately 5-fold within two hours and begin to decrease within four hours during an oral lipid tolerance test in humans.2 Serum levels of TCDCA are increased in patients with liver cirrhosis and may serve as a marker of disease progression.3 TCDCA MaxSpec® standard is a quantitative grade standard of TCDCA 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 TCDCA 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
1. Hoffman, A.F. The continuing importance of bile acids in liver and intestinal disease. Arch. Intern. Med. 159(22), 2647-2658 (1999).
2. 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).
3. Wang, X., Xie, G., Zhao, A., et al. Serum bile acids are associated with pathological progression of hepatitis B-induced cirrhosis. J. Proteome Res. 15(4), 1126-1134 (2016).
String Representations
InChiKey (Click to copy)
BHTRKEVKTKCXOH-BJLOMENOSA-N
InChi (Click to copy)
InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,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])C[C@@H](O)[C@@]21[H]
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
34
Rings
4
Aromatic Rings
0
Rotatable Bonds
7
Van der Waals Molecular Volume
488.53
Topological Polar Surface Area
123.93
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
7
logP
5.79
Molar Refractivity
132.35
Admin
Created at
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Updated at
24th Apr 2024