Wikipedia

Taurodeoxycholic acid

Taurodeoxycholic acid is a bile acid. This compound is a closely related isomer of taurochenodeoxycholic acid and tauroursodeoxycholic acid sharing the exact molecular formula and molecular weight.

Taurodeoxycholic acid
Names
IUPAC name
2-(3α,12α-Dihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid
Systematic IUPAC name
2-{(2R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11S,11aR)-7,11-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}ethane-1-sulfonic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: AWDRATDZQPNJFN-VAYUFCLWSA-N checkY
  • InChI=1/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
    Key: AWDRATDZQPNJFN-VAYUFCLWBR
  • C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Properties
C26H45NO6S
Molar mass 499.71 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Taurodeoxycholic acid and its isomers have molecular masses similar to perfluorooctanesulfonic acid (PFOS) and therefore may interfere with interpretation of mass spectrometry data, leading to a false indication of the presence of PFOS in a biological sample.[1]

Serum concentration of taurodeoxycholic acid, a downstream microbial metabolite of cholic acid, is associated with a strong increased risk of colorectal cancer among women.[2]

Also, the determination of taurodeoxycholic acid 3-sulfate in blood samples may potentially be useful as a risk factor and screening biomarker for lung cancer prevention.[3]

References

edit
  1. ^ Benskin, Jonathan P.; Bataineh, Mahmoud; Martin, Jonathan W. (2007). "Simultaneous Characterization of Perfluoroalkyl Carboxylate, Sulfonate, and Sulfonamide Isomers by Liquid Chromatography−Tandem Mass Spectrometry". Analytical Chemistry. 79 (17): 6455–6464. doi:10.1021/ac070802d. PMID 17665875.
  2. ^ Loftfield E, Falk RT, Sampson JN, Huang WY, Hullings A, Murphy G, Weinstein SJ, Albanes D, Freedman ND, Sinha R. Prospective Associations of Circulating Bile Acids and Short-Chain Fatty Acids With Incident Colorectal Cancer. JNCI Cancer Spectr. 2022 May 2;6(3):pkac027. doi: 10.1093/jncics/pkac027. PMID: 35583137; PMCID: PMC9115675.
  3. ^ Tang Z, Liang D, Deubler EL, Sarnat JA, Chow SS, Diver WR, Wang Y (June 2024). "Lung cancer metabolomics: a pooled analysis in the Cancer Prevention Studies". BMC Med. 22 (1): 262. doi:10.1186/s12916-024-03473-1. PMC 11197282. PMID 38915026.
 

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