Structure Database (LMSD)
Common Name
Ursodeoxycholic acid
Systematic Name
3α,7β-Dihydroxy-5β-cholan-24-oic Acid
Synonyms
- Ursodiol
- Ursodeoxycholate
- UDCA
LM ID
LMST04010033
Formula
Exact Mass
Calculate m/z
392.292661
Sum Composition
Status
Curated
3D model of Ursodeoxycholic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Ursodeoxycholic acid (UDCA) is a secondary bile acid formed via epimerization of chenodeoxycholic acid (CDCA).1,2 UDCA is also a metabolite of lithocholic acid (LCA) in human liver microsomes.3 It inhibits taurocholic acid uptake in HeLa cells expressing recombinant human sodium/taurocholate cotransporting polypeptide (NTCP) with an IC50 value of 3.6 μM.4 UDCA (50 μM) inhibits apoptosis induced by deoxycholic acid (DCA) or ethanol in primary rat hepatocytes.5 Dietary administration of UDCA blocks DCA-induced increases in the number of TUNEL-positive hepatocytes in rats. Formulations containing UDCA have been used in the treatment of primary biliary cirrhosis.
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
RUDATBOHQWOJDD-UZVSRGJWSA-N
InChi (Click to copy)
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])[C@@H](O)C[C@]2([H])C[C@H](O)C1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
BBA0033
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
4
Aromatic Rings
0
Rotatable Bonds
4
Van der Waals Molecular Volume
406.84
Topological Polar Surface Area
77.76
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
5.05
Molar Refractivity
109.67
Admin
Created at
-
Updated at
5th Mar 2024