Tauroursodeoxycholic acid dihydrateProduct ingredient for Tauroursodeoxycholic acid
- Name
- Tauroursodeoxycholic acid dihydrate
- Drug Entry
- Tauroursodeoxycholic acid
Tauroursodeoxycholic acid, also known as ursodoxicoltaurine, is a highly hydrophilic tertiary bile acid 3 that is produced in humans at a low concentration.3 It is a taurine conjugate of ursodeoxycholic acid 2 with comparable therapeutic efficacy and safety,3 but a much higher hydrophilicity.1 Normally, hydrophilic bile acids regulates hydrophobic bile acids and their cytotoxic effects. Tauroursodeoxycholic acid can reduce the absorption of cholesterol in the small intestine, thereby reducing the body's intake of dietary cholesterol and the body cholesterol content.4
Tauroursodeoxycholic acid is currently used in Europe to treat and prevent gallstones as a bile acid derivative.7 Due to a range of its molecular properties - namely its anti-apoptotic effects - tauroursodeoxycholic acid has been examined in inflammatory metabolic diseases and neurodegenerative diseases.2,3
- Accession Number
- DBSALT003104
- Structure
Structure for Tauroursodeoxycholic acid dihydrate (DBSALT003104)
- Synonyms
- Taurursodiol dihydrate / Ursodoxicoltaurine dihydrate
- UNII
- U7XRV7RZ1I
- CAS Number
- 117609-50-4
- Weight
- Average: 535.74
Monoisotopic: 535.317888716 - Chemical Formula
- C26H49NO8S
- InChI Key
- BNXLUNVCHFIPFY-GUBAPICVSA-N
- InChI
- InChI=1S/C26H45NO6S.2H2O/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);2*1H2/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-;;/m1../s1
- IUPAC Name
- 2-[(4R)-4-[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido]ethane-1-sulfonic acid dihydrate
- SMILES
- O.O.[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
- External Links
- ChemSpider
- 30653682
- Predicted Properties
Property Value Source Water Solubility 0.00748 mg/mL ALOGPS logP 1.38 ALOGPS logP 1.1 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) -0.8 Chemaxon pKa (Strongest Basic) -0.32 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 123.93 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 130.68 m3·mol-1 Chemaxon Polarizability 56.72 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon