Lithocholic acid taurine conjugate
Basic information
- CAS
516-90-5- Standard SMILES
CC(CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
QBYUNVOYXHFVKC-JIOVCDOMSA-N- Molecular formula
- C26H45NO5S
- Average molar mass
- 483.7 g/mol
- Monoisotopic mass
- 483.30184471
Names & identifiers
- Preferred name
- Lithocholic acid taurine conjugate
- IUPAC
- 2-[4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid
- English name
- 2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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
- Molecular formula
- C26H45NO5S
- Molecular weight
- 483.7
Names & synonyms
Lithocholic acid taurine conjugate2-[4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acidTaurine, N-(3-alpha-hydroxy-5-beta-cholan-24-oyl)-SCHEMBL187621712-(((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)amino)ethanesulfonic acidEthanesulfonic acid, 2-(((3-alpha,5-beta)-3-hydroxy-24-oxocholan-24-yl)amino)-LithocholyltaurineApigenine Impurity 6Cholic acid Impurity 72Taurolithocholic Acid D8Taurolithocholic Acid(TLCA)Taurodeoxycholic Acid Impurity 3
Show more names
Taurolithocholic Acid MaxSpec? StandardN-(3α-Hydroxy-24-oxo-5β-cholan-24-yl)taurine5β-CHOLANIC ACID-3α-OL N-(2-SULPHOETHYL)-AMIDE
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 825
Physicochemical properties
- Melting point
- 212 · 212-213 °C
- Density
- 1.0476 · 1.0476 (rough estimate)
- refractive index
- 1.565 · 1.5650 (estimate)
- storage temp.
- -20 °C · -20°C
- form
- powder
- pka
- 1.42 · 1.42±0.50(Predicted)
- color
- Colorless to light yellow
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 2 · GHS02,GHS08
- Signal word
- Danger
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS08
Chemistry & industry
Applications
UsesTaurolithocholic acid is a bile acid that has the activity of increasing cell viability, inducing the S phase of the cell cycle, and promoting DNA synthesis in a concentration-dependent manner in the intrahepatic cholangiocarcinoma cell line RMCCA-1. It can also increase the phosphorylation of EGFR and ERK 1/2 and the expression of cyclin D1 in RMCCA-1 cells, and its induced RMCCA-1 cell growth can be inhibited by specific antagonists and inhibitors.
Additional notes
DefinitionChEBI: Taurolithocholic acid is the bile acid taurine conjugate of lithocholic acid. It has a role as a human metabolite. It is a monocarboxylic acid amide and a bile acid taurine conjugate. It is functionally related to a lithocholic acid. It is a conjugate acid of a taurolithocholate.
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