taurocholic acid

Also known as TCA, 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acid 24-taurine, N-choloyltaurine, cholic acid taurine conjugate, 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid, 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-tris(oxidanyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid, 2-[[(4R)-1-oxo-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl]amino]ethanesulfonic acid, N-Choloyl-Taurine

yellowish crystalline bile acid

Chemical data

Formula: C26H45NO7S
Molecular weight: 515.7 g/mol
IUPAC name: 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
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]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
InChIKey: WBWWGRHZICKQGZ-HZAMXZRMSA-N
XLogP: 2.2
Polar surface area: 153 Å²
H-bond donors: 5
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

6,119 papers

Taurocholic acid promotes hepatic stellate cell activation via S1PR2/p38 MAPK/YAP signaling under cholestatic conditions.Clinical and molecular hepatology · 2023
Taurocholic acid metabolism by gut microbes and colon cancer.Gut microbes · 2016
Deconjugating taurocholic acid with Bifidobacterium to mitigate obesity-driven cancer progression by restoring CD8(+) T-cell infiltration.NPJ biofilms and microbiomes · 2025
Taurocholic Acid Is Associated With Disturbed Functional Connectivity in the Hippocampus of Patients With Depression.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026
Taurocholic acid lowers the inflammatory response of gingival fibroblasts, epithelial cells, and macrophages.Journal of oral science · 2020

via PubMed

Wikidata facts

Subclass of: bile acids
Has part: carbon
Mass: 515.292
Has use: detergent

Show 6 more facts

chemical formula: C₂₆H₄₅NO₇S
canonical SMILES: CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
isomeric 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]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
found in taxon: Caenorhabditis elegans
has characteristic: bitterness
Commons category: Taurocholic acid

Sources (4)

via Wikidata · CC0