Taurochenodeoxycholic acid

Taurochenodeoxycholic acid is a bile acid formed in the liver of most species, including humans, by conjugation of chenodeoxycholic acid with taurine.^[1] It is secreted into bile and then into the intestine.^[2] It is usually ionized at physiologic pH. However, although it can be crystallized as the sodium salt.

Taurochenodeoxycholic acid

Names
IUPAC name 2-(3α,7α-Dihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid
Systematic IUPAC name 2-{(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}ethane-1-sulfonic acid
Other names 12-Deoxycholyltaurine; 12-Desoxycholyltaurine; Chenodeoxycholyltaurine; Chenyltaurine
Identifiers
CAS Number	516-35-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16525 Y
ChEMBL	ChEMBL185878 Y
ChemSpider	343282 Y
IUPHAR/BPS	4747
PubChem CID	387316
UNII	651KU15938 Y
CompTox Dashboard (EPA)	DTXSID101020121
InChI 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 Y Key: BHTRKEVKTKCXOH-BJLOMENOSA-N Y InChI=1/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 Key: BHTRKEVKTKCXOH-BJLOMENOBE
SMILES O=S(=O)(O)CCNC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]4[C@H]2[C@H](O)C[C@@H]3C[C@H](O)CC[C@@]34C)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

It acts as a detergent to solubilize fats in the small intestine and is itself absorbed by active transport in the terminal ileum.^[3]

It is used as a cholagogue and choleretic.

Substantial evidence indicates that high circulating bile acids promote colon cancer risk.^[4][5] In a prospective study, positive associations were observed between prediagnostic plasma levels of seven conjugated bile acid metabolites, including taurochenodeoxycholic acid, and colon cancer risk.^[4]

See also

• Tauroursodeoxycholic acid, an epimer
• See article about Taurodeoxycholic acid as an interferent in Perfluorooctanesulfonic acid (PFOS) mass spectrometry analysis.