Taurodeoxycholic acid

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477861003

| ImageFile = Taurodeoxycholic acid.png

| ImageSize = 200px

| IUPACName = 2-(3α,12α-Dihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid

| SystematicName = 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

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 516-50-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 20668G0RPI

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 412272

| PubChem = 2733768

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 9410

| 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

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2015539

| 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

| InChIKey = AWDRATDZQPNJFN-VAYUFCLWBR

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = AWDRATDZQPNJFN-VAYUFCLWSA-N

}}

|Section2={{Chembox Properties

| C=26 | H=45 | N=1 | O=6 | S=1

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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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 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.{{Cite journal | doi = 10.1021/ac070802d | title = Simultaneous Characterization of Perfluoroalkyl Carboxylate, Sulfonate, and Sulfonamide Isomers by Liquid Chromatography−Tandem Mass Spectrometry | date = 2007 | last1 = Benskin | first1 = Jonathan P. | last2 = Bataineh | first2 = Mahmoud | last3 = Martin | first3 = Jonathan W. | journal = Analytical Chemistry | volume = 79 | issue = 17 | pages = 6455–64 | pmid = 17665875 }}

Serum concentration of taurodeoxycholic acid, a downstream microbial metabolite of cholic acid, is associated with a strong increased risk of colorectal cancer among women.{{cite journal |vauthors=Loftfield E, Falk RT, Sampson JN, Huang WY, Hullings A, Murphy G, Weinstein SJ, Albanes D, Freedman ND, Sinha R |title=Prospective Associations of Circulating Bile Acids and Short-Chain Fatty Acids With Incident Colorectal Cancer |journal=JNCI Cancer Spectr |volume=6 |issue=3 |pages=pkac027 |date=May 2022 |pmid=35583137 |pmc=9115675 |doi=10.1093/jncics/pkac027 }}

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.{{cite journal |vauthors=Tang Z, Liang D, Deubler EL, Sarnat JA, Chow SS, Diver WR, Wang Y |title=Lung cancer metabolomics: a pooled analysis in the Cancer Prevention Studies |journal=BMC Med |volume=22 |issue=1 |pages=262 |date=June 2024 |pmid=38915026 |pmc=11197282 |doi=10.1186/s12916-024-03473-1 |doi-access=free }}