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





Classification

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ursus americanus (#9643)
Mammalia (#40674)
Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores.,
J Lipid Res, 1993
Pubmed ID: 8263415

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

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Created at
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Updated at
5th Mar 2024