Structure Database (LMSD)
Common Name
Norursodeoxycholic acid
Systematic Name
24-nor-3α,7β-dihydroxy-5β-cholan-23-oic acid
Synonyms
LM ID
LMST04060021
Formula
Exact Mass
Calculate m/z
378.27701
Sum Composition
Status
Curated
3D model of Norursodeoxycholic 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
Norursodeoxycholic acid (norUDCA) is a bile acid and the C23 homolog of UDCA .1,2 Unlike UDCA, norUDCA does not undergo conjugation to taurine or glycine and is secreted in an unchanged form, as trihydroxy derivatives, or as sulfate or glucuronide conjugates. Dietary administration of norUDCA (0.5% w/w) decreases serum levels of alanine aminotransferase (ALT) and alkaline phosphatase, markers of cholestasis, periductal fibrosis, and hepatic hydroxyproline content in an Mdr2-/- mouse model of sclerosing cholangitis.1
This information has been provided by Cayman Chemical
References
1. Fickert, P., Wagner, M., Marschall, H.-U., et al. 24-norUrsodeoxycholic acid is superior to ursodeoxycholic acid in the treatment of sclerosing cholangitis in Mdr2 (Abcb4) knockout mice. Gastroenterology 130(2), 465-481 (2006).
String Representations
InChiKey (Click to copy)
QYYDXDSPYPOWRO-JHMCBHKWSA-N
InChi (Click to copy)
InChI=1S/C23H38O4/c1-13(10-20(26)27)16-4-5-17-21-18(7-9-23(16,17)3)22(2)8-6-15(24)11-14(22)12-19(21)25/h13-19,21,24-25H,4-12H2,1-3H3,(H,26,27)/t13-,14+,15-,16-,17+,18+,19+,21+,22+,23-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CC(=O)O)CC[C@@]4([H])[C@]3([H])[C@@H](O)C[C@]2([H])C[C@H](O)C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
4
Aromatic Rings
0
Rotatable Bonds
3
Van der Waals Molecular Volume
389.54
Topological Polar Surface Area
77.76
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
4.66
Molar Refractivity
105.05
Admin
Created at
-
Updated at
9th Jun 2022