:Taurochenodeoxycholic acid

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477860939

| ImageFile=Taurochenodeoxycholic acid.svg

| ImageSize=200px

| IUPACName=2-(3α,7α-Dihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid

| SystematicName=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

| OtherNames=12-Deoxycholyltaurine; 12-Desoxycholyltaurine; Chenodeoxycholyltaurine; Chenyltaurine

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4747

| CASNo=516-35-8

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

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

| UNII = 651KU15938

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

| ChEMBL = 185878

| PubChem = 387316

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

| ChemSpiderID = 343282

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

| ChEBI = 16525

| 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

| 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

| InChIKey = BHTRKEVKTKCXOH-BJLOMENOBE

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

| StdInChI = 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

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

| StdInChIKey = BHTRKEVKTKCXOH-BJLOMENOSA-N

}}

|Section2={{Chembox Properties

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

| Appearance=

| Density=

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| Solubility=

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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Taurochenodeoxycholic acid is a bile acid formed in the liver of most species, including humans, by conjugation of chenodeoxycholic acid with taurine.{{cite journal |author=Hofmann AF |title=The continuing importance of bile acids in liver and intestinal disease |journal=Arch. Intern. Med. |volume=159 |issue=22 |pages=2647–58 |year=1999 |pmid=10597755 |doi= 10.1001/archinte.159.22.2647|s2cid=21211064 |doi-access= }} It is secreted into bile and then into the intestine.{{cite journal | vauthors = Perez de la Cruz Moreno M, Oth M, Deferme S, Lammert F, Tack J, Dressman J, Augustijns P | title = Characterization of fasted-state human intestinal fluids collected from duodenum and jejunum | journal = The Journal of Pharmacy and Pharmacology | volume = 58 | issue = 8 | pages = 1079–89 | date = August 2006 | pmid = 16872555 | doi = 10.1211/jpp.58.8.0009 | url = | doi-access = free }} 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.{{cite journal | vauthors = Carey MC, Small DM | title = Micelle formation by bile salts. Physical-chemical and thermodynamic considerations | journal = Archives of Internal Medicine | volume = 130 | issue = 4 | pages = 506–27 | date = October 1972 | pmid = 4562149 | doi = 10.1001/archinte.1972.03650040040005| url = }}

It is used as a cholagogue and choleretic.

Substantial evidence indicates that high circulating bile acids promote colon cancer risk.{{cite journal |vauthors=Kühn T, Stepien M, López-Nogueroles M, Damms-Machado A, Sookthai D, Johnson T, Roca M, Hüsing A, Maldonado SG, Cross AJ, Murphy N, Freisling H, Rinaldi S, Scalbert A, Fedirko V, Severi G, Boutron-Ruault MC, Mancini FR, Sowah SA, Boeing H, Jakszyn P, Sánchez MJ, Merino S, Colorado-Yohar S, Barricarte A, Khaw KT, Schmidt JA, Perez-Cornago A, Trichopoulou A, Karakatsani A, Thriskos P, Palli D, Agnoli C, Tumino R, Sacerdote C, Panico S, Bueno-de-Mesquita B, van Gils CH, Heath AK, Gunter MJ, Riboli E, Lahoz A, Jenab M, Kaaks R |title=Prediagnostic Plasma Bile Acid Levels and Colon Cancer Risk: A Prospective Study |journal=J Natl Cancer Inst |volume=112 |issue=5 |pages=516–524 |date=May 2020 |pmid=31435679 |pmc=7225675 |doi=10.1093/jnci/djz166 |url=}}{{cite journal |vauthors=Bernstein H, Bernstein C |title=Bile acids as carcinogens in the colon and at other sites in the gastrointestinal system |journal=Exp Biol Med (Maywood) |volume=248 |issue=1 |pages=79–89 |date=January 2023 |pmid=36408538 |pmc=9989147 |doi=10.1177/15353702221131858 |url=}} 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.