2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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
2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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 Basic information
- Product Name:
- 2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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
- Synonyms:
-
- 2-[[(3a,5,12)-3,12-Dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic Acid
- Deoxycholyltaurine
- Deoxytaurocholic Acid
- N-(3a,12a-Dihydroxy-5-cholan-24-oyl)taurine
- Taurodeoxychloic Acid
- Taurodesoxycholic Acid
- Tudcabil
- 2-[[(3α,5β,12α)-3,12-Dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic acid
- CAS:
- 516-50-7
- MF:
- C26H45NO6S
- MW:
- 499.7
- Product Categories:
-
- Chiral Reagents
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Steroids
- Mol File:
- 516-50-7.mol
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2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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 Chemical Properties
- Melting point:
- 175-200 °C
- Density
- 1.216±0.06 g/cm3(Predicted)
- storage temp.
- -20°C
- solubility
- DMSO (Slightly, Heated, Sonicated), Methanol (Slightly, Heated, Sonicated)
- form
- Solid
- pka
- 1.42±0.50(Predicted)
- color
- White to Off-White
- Stability:
- Hygroscopic
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2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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 Usage And Synthesis
Uses
Deoxycholyltaurine rescues human colon cancer cells from apoptosis by activating EGFR-dependent PI3K/Akt signaling.
Definition
ChEBI: A bile acid taurine conjugate of deoxycholic acid.
in vivo
Taurodeoxycholic acid (1.25-5 mg/kg, p.o., 6 days) ameliorates dextran sodium sulfate (DSS)-induced colitis in mice[9].
Taurodeoxycholic acid (Taurodeoxycholic acid form, 50 mg/kg; i.p.; once daliy for 34 d) prevents neuropathology and associated behavioral deficits in the 3-nitropropionic acid rat model of Huntington's disease (HD) [10].
Taurodeoxycholic acid (Taurodeoxycholic acid form, 500 mg/kg; s.c.; once every 3 d for 7 weeks) leads to a significant reduction in striatal neuropathology of the R6/2 transgenic HD mouse[11].
Taurodeoxycholic acid (0.5 mg/kg; i.v., once) confers protection to C57BL/6N mice with sepsis, but does not protect TGR5 KO mice under sepsis[12].
| Animal Model: | A mouse colitis model (fed with 3% (w/v) DSS in drinking water for the first seven days and then switched to normal drinking water for an additional two days)[9] |
| Dosage: | 1.25, 2.5, and 5 mg/kg |
| Administration: | Oral gavage (p.o.), from day 3 to day 8, once a day |
| Result: | Prevented loss of body weight, shortening of the colon, production of pro-inflammatory cytokines, infiltration of pro-inflammatory cells, and mucosal ulceration in the colon. |
| Animal Model: | Huntington's disease model in mouse[10] |
| Dosage: | 50 mg/kg |
| Administration: | Intraperitoneal injection; once daliy for 34 d, injected 3-NP at 6 hr after Taurodeoxycholic acid treatment |
| Result: | Reduced striatal atrophy, decreased striatal apoptosis, as well as fewer and smaller size ubiquitinated neuronal intranuclear huntingtin inclusions. Significantly improved locomotor and sensorimotor deficits. |
| Animal Model: | C57BL/6N mice, Lipopolysaccharides (HY-D1056) injection model of sepsis[12] |
| Dosage: | 0.5 mg/kg |
| Administration: | Intravenous injection, 30 min or 24 h after LPS injection |
| Result: | Improved the survival rate of mice with sepsis. Decreased liver and kidney damage in septic mice. Ameliorated systemic inflammation and normalized blood pressure in septic mice. |
IC 50
Microbial Metabolite
2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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 acidSupplier
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2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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(516-50-7)Related Product Information
- Taurohyodeoxycholic acid sodium salt hydrate
- taurohyodeoxycholic acid
- Taurohyodeoxycholic Acid-d5
- Taurohyodeoxycholic Acid Sodium Salt-d5
- 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
- Taurohyodeoxycholic Acid Sodium Salt Impurity 1
- Tauroursodeoxycholic acid