Basic information
- CAS
516-90-5- Standard SMILES
C[C@H](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-GBURMNQMSA-N- Molecular formula
- C26H45NO5S
- Average molar mass
- 483.7 g/mol
- Monoisotopic mass
- 483.30184454
Overview
Taurolithocholic acid is the bile acid taurine conjugate of lithocholic acid. It has a role as a human metabolite. It is a bile acid taurine conjugate and a monocarboxylic acid amide. It is functionally related to a lithocholic acid. It is a conjugate acid of a taurolithocholate.
Names & identifiers
- Preferred name
- Taurolithocholic Acid
- IUPAC
- 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
- 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
TAUROLITHOCHOLIC ACID516-90-5LithocholyltaurineDTXSID209659252-[[(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 acidCHEBI:36259N-(3alpha-hydroxy-5beta-cholan-24-oyl)-taurineAcid, TaurolithocholicLithocholate, TaurineEthanesulfonic acid, 2-(((3alpha,5beta)-3-hydroxy-24-oxocholan-24-yl)amino)-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 acidRefChem:389301
Show more names
Apigenine Impurity 6Cholic acid Impurity 72Taurolithocholic Acid D8Taurodeoxycholic Acid Impurity 3Taurolithocholic Acid MaxSpec? StandardN-(3α-Hydroxy-24-oxo-5β-cholan-24-yl)taurine
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
Experimental & physicochemical properties
Chemical ClassesBile Acids -> Quant Bile Acids
LipidsLipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Taurine conjugates [ST0504]
Melting Point212 - 213 °C
Physical DescriptionSolid
Collision Cross Section
212.4 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]
204.62 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
213.1 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
206.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated]
206.5 Ų [M-H]-
Physicochemical properties
- Melting point
- 212 · 212-213 °C
- Density
- 1.0476 · 1.0476 (rough estimate)
- refractive index
- 1.565 · 1.5650 (estimate)
Safety & regulation
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS08
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic).
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Metabolite Pathways27-Hydroxylase Deficiency
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.
Suppliers26 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
奥夫仑医药（四川）有限公司17336178085 · [email protected]
上海科骊科生物技术有限公司021-34975789 18721102763
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
Related reactions
2 records
Compound notes
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