Structure Database (LMSD)

Common Name
Taurodeoxycholic acid
Systematic Name
N-(3α,12α-dihydroxy-5β-cholan-24-oyl)-taurine
Synonyms
  • Taurodeoxycholate
LM ID
LMST05040013
Formula
Exact Mass
Calculate m/z
499.296761
Sum Composition
Status
Curated




Classification

Biological Context

Taurodeoxycholic acid is a taurine-conjugated form of the secondary bile acid deoxycholic acid .1 Taurodeoxycholic acid stimulates chloride ion secretion through calcium-activated chloride ion channels and cystic fibrosis transmembrane conductance regulator (CFTR) in Calu-3 airway epithelial cell monolayers when applied basolaterally.2 Serum levels of taurodeoxycholic acid increase approximately 5-fold within two hours during an oral lipid tolerance test in humans.1 Taurodeoxycholic acid MaxSpec® standard is a quantitative grade standard of taurodeoxycholic acid 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 taurodeoxycholic acid 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. 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).

String Representations

InChiKey (Click to copy)
AWDRATDZQPNJFN-VAYUFCLWSA-N
InChi (Click to copy)
InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1
SMILES (Click to copy)
[C@]12(CC[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@H](O)[C@]1(C)[C@@]([H])([C@@](C)([H])CCC(=O)NCCS(=O)(O)=O)CC[C@@]21[H])[H]

Other Databases

Wikipedia
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB 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
-
Updated at
24th Apr 2024