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.

Quick facts Names, Identifiers ...

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
CAS Number	516-50-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9410 Y
ChEMBL	ChEMBL412272 Y
ChemSpider	2015539 Y
PubChem CID	2733768
UNII	20668G0RPI Y
CompTox Dashboard (EPA)	DTXSID00873418
InChI 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 Y Key: AWDRATDZQPNJFN-VAYUFCLWSA-N Y 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
SMILES 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
Chemical formula	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). N verify (what is YN ?) Infobox references

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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]