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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40O5
Molecular Weight 408.5714
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URSOCHOLIC ACID

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])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

InChI

InChIKey=BHQCQFFYRZLCQQ-UTLSPDKDSA-N
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1

HIDE SMILES / InChI
Ursocholic acid (UCA) is the 7 beta epimer of the naturally occurring primary bile acid, cholic acid. Cholic acid (CA) administration does not reduce biliary cholesterol saturation unless its 7 alpha dehydroxylation to deoxycholic acid (DCA) is prevented by concomitant antibiotic treatment. It was shown, that UCA caused diarrhoea and hypercholesterolemia, had only a modest effect on biliary cholesterol saturation and thus UCA was not able to replace ursodeoxycholic and chenodeoxycholic acid for medical treatment of gallstones. In addition, as discovered, during ursocholic acid therapy the synthesis of primary bile acids continued whereas the formation of secondary bile acids was greatly increase.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Effect of ursocholic acid on bile lipid secretion and composition.
1986 Apr
Effect of chronic ursocholic acid administration on bile lipid composition and bile acid pool size in gallstone patients.
1990 Jul
Metabolism of ursocholic acid in humans: conversion of ursocholic acid to deoxycholic acid.
1992 Apr
Ursocholic acid, a hydrophilic bile acid, fails to improve liver function parameters in primary biliary cirrhosis: comparison with ursodeoxycholic acid.
1997 Jun
A paucity of unusual trihydroxy bile acids in the urine of patients with severe liver diseases.
1999 May
FXR-activating ligands inhibit rabbit ASBT expression via FXR-SHP-FTF cascade.
2005 Jan
Patents

Patents

Sample Use Guides

were fed ursocholic acid 900 mg/day
Route of Administration: Oral
Caco-2 cells were treated with 10 μM hydrophobic bile acids DCA, CDCA, and CA, which activate FXR, and 10 μM ursocholic acid (UCA), which almost do not activate FXR, for 40 h. Neither UCA nor ursochenodeoxycholic acid (UDCA) significantly reduced luciferase activity in P2 with intact α-fetoprotein transcription factor (FTF) binding site.
Name Type Language
URSOCHOLIC ACID
Common Name English
7-EPICHOLIC ACID
Common Name English
URSODEOXYCHOLIC ACID IMPURITY D [EP IMPURITY]
Common Name English
3.ALPHA.,7.BETA.,12.ALPHA.-TRIHYDROXY-5.BETA.-CHOLANIC ACID
Systematic Name English
URSOCHOLIC ACID [EP IMPURITY]
Common Name English
3.ALPHA.,7.BETA.,12.ALPHA.-TRIHYDROXY-5 BETA-CHOLAN-24-OIC ACID
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID301018756
Created by admin on Fri Dec 15 15:17:49 GMT 2023 , Edited by admin on Fri Dec 15 15:17:49 GMT 2023
PRIMARY
CHEBI
81240
Created by admin on Fri Dec 15 15:17:49 GMT 2023 , Edited by admin on Fri Dec 15 15:17:49 GMT 2023
PRIMARY
FDA UNII
MLP1T05RBX
Created by admin on Fri Dec 15 15:17:49 GMT 2023 , Edited by admin on Fri Dec 15 15:17:49 GMT 2023
PRIMARY
PUBCHEM
122340
Created by admin on Fri Dec 15 15:17:49 GMT 2023 , Edited by admin on Fri Dec 15 15:17:49 GMT 2023
PRIMARY
EVMPD
SUB11390MIG
Created by admin on Fri Dec 15 15:17:49 GMT 2023 , Edited by admin on Fri Dec 15 15:17:49 GMT 2023
PRIMARY
CAS
2955-27-3
Created by admin on Fri Dec 15 15:17:49 GMT 2023 , Edited by admin on Fri Dec 15 15:17:49 GMT 2023
PRIMARY