Taurochenodeoxycholic acid

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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
  • 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
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

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

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

It is used as a cholagogue and choleretic.

Substantial evidence indicates that high circulating bile acids promote colon cancer risk. 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.