Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C26H43NO5 |
| Molecular Weight | 449.6233 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[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)NCC(O)=O
InChI
InChIKey=GHCZAUBVMUEKKP-XROMFQGDSA-N
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
| Molecular Formula | C26H43NO5 |
| Molecular Weight | 449.6233 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| pH-Solubility relations of chenodeoxycholic and ursodeoxycholic acids: physical-chemical basis for dissimilar solution and membrane phenomena. | 1980 Jan |
|
| Positions of conjugation of bile acids with glucose and N-acetylglucosamine in vitro. | 1994 Sep |
|
| Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. | 1998 Jan |
|
| Whole-cell response characteristics of ciliated and microvillous olfactory receptor neurons to amino acids, pheromone candidates and urine in rainbow trout. | 2001 Nov |
|
| Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. | 2005 Jan |
|
| Uptake of ursodeoxycholate and its conjugates by human hepatocytes: role of Na(+)-taurocholate cotransporting polypeptide (NTCP), organic anion transporting polypeptide (OATP) 1B1 (OATP-C), and oatp1B3 (OATP8). | 2006 Jan-Feb |
|
| Human multidrug resistance protein 2 transports the therapeutic bile salt tauroursodeoxycholate. | 2007 Feb |
|
| p53 is a key molecular target of ursodeoxycholic acid in regulating apoptosis. | 2007 Nov 23 |
|
| Glycoursodeoxycholic acid and interleukin-10 modulate the reactivity of rat cortical astrocytes to unconjugated bilirubin. | 2007 Sep |
|
| Combination of ursodeoxycholic acid and glucocorticoids upregulates the AE2 alternate promoter in human liver cells. | 2008 Feb |
|
| Determination of bile acids in human serum by on-line restricted access material-ultra high-performance liquid chromatography-mass spectrometry. | 2008 Jun 15 |
|
| Bilirubin injury to neurons: contribution of oxidative stress and rescue by glycoursodeoxycholic acid. | 2008 Mar |
|
| Contribution of inflammatory processes to nerve cell toxicity by bilirubin and efficacy of potential therapeutic agents. | 2009 |
|
| Effect of SLCO1B1 polymorphism on the plasma concentrations of bile acids and bile acid synthesis marker in humans. | 2009 Jun |
|
| Protective effects of glycoursodeoxycholic acid in Barrett's esophagus cells. | 2010 Feb |
|
| Bilirubin selectively inhibits cytochrome c oxidase activity and induces apoptosis in immature cortical neurons: assessment of the protective effects of glycoursodeoxycholic acid. | 2010 Jan |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:30:00 UTC 2023
by
admin
on
Sat Dec 16 09:30:00 UTC 2023
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| Record UNII |
PF1G5J2X2A
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| Record Status |
Validated (UNII)
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| Record Version |
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| Code System | Code | Type | Description | ||
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89929
Created by
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12310288
Created by
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PF1G5J2X2A
Created by
admin on Sat Dec 16 09:30:00 UTC 2023 , Edited by admin on Sat Dec 16 09:30:00 UTC 2023
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DTXSID20862344
Created by
admin on Sat Dec 16 09:30:00 UTC 2023 , Edited by admin on Sat Dec 16 09:30:00 UTC 2023
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64480-66-6
Created by
admin on Sat Dec 16 09:30:00 UTC 2023 , Edited by admin on Sat Dec 16 09:30:00 UTC 2023
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
Unit: ng/mg creatinine; healthy volunteers (n=12)
IN-VIVO
URINE
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||
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METABOLITE -> PARENT |
IN-VIVO
FECAL
|
||
|
METABOLITE -> PARENT |
Unit: percent of total bile acids; Daily dose of UDCA: 1g (n=3); Duration: 2 weeks
IN-VIVO
FECAL
|
||
|
METABOLITE TOXIC -> PARENT |
IN-VIVO
FECAL
|
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|
PARENT -> METABOLITE |
MAJOR
PLASMA
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METABOLITE -> PARENT |
IN-VITRO
Scientific Literature
|
||
|
METABOLITE -> PARENT |
IN-VIVO
URINE
|
||
|
METABOLITE -> PARENT |
LCA-sulfate in serum of gallstone patients given UDCA (n=7; 750mg/day [250mg in the morning, 500mg in the evening] for 2 to 3 weeks); Control (n=5): 0.1 micromole/L
IN-VIVO
PLASMA
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|
METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE ACTIVE -> PARENT |
IN-VIVO
URINE
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|
METABOLITE -> PARENT |
Unit: micromole/24hr (baseline: 0.12 mcmol/24hr); Excretion of LCA-sulfate on day 10 of daily oral administration of 750mg UDCA to healthy volunteers
IN-VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN-VIVO
URINE
|
||
|
METABOLITE -> PARENT |
Unit: micromole/g creatinine; LCA-sulfate in urine of gallstone patients given UDCA (n=6; 750mg/day [250mg in the morning, 500mg in the evening] for 2 to 3 weeks); Control (n=6): 0.4 micromole/g creatinine
IN-VIVO
URINE
|
||
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METABOLITE -> PARENT |
IN-VIVO
FECAL
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||
|
METABOLITE TOXIC -> PARENT |
IN-VIVO
FECAL
|
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|
METABOLITE -> PARENT |
IN-VIVO
URINE
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||
|
METABOLITE TOXIC -> PARENT |
IN-VIVO
FECAL
|
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METABOLITE -> PARENT |
IN-VIVO
URINE
|
||
|
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METABOLITE -> PARENT |
IN-VITRO
Scientific Literature
|
||
|
METABOLITE -> PARENT |
Unit: percent of total bile acids; Daily dose of UDCA: 15mg/kg (n=6); Duration: 15 days; before treatment (7-KLCA in feces): 1 % of total bile acids
IN-VIVO
FECAL
|
