Structure Database (LMSD)
Common Name
Taraxasterol
Systematic Name
18α,19α-urs-20(30)-en-3β-ol
Synonyms
3D model of Taraxasterol
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
Level 4 Class
Biological Context
Taraxasterol is a pentacyclic triterpene that has been found in T. mongolicum and has diverse biological activities.1,2,3 It decreases LPS-induced increases in the secreted levels of nitrite, prostaglandin E2 (PGE2), TNF-α, IL-1β, and IL-6 from RAW 264.7 macrophages when used at concentrations of 5 and 12.5 µg/ml.1 Taraxasterol reduces the levels of hepatitis B virus (HBV) surface antigen (HBsAg), HBV e antigen (HBeAg), and HBV DNA secreted from HBV-infected HepG2 2.2.15 hepatocytes in a concentration-dependent manner.2 In vivo, taraxasterol (10 mg/kg per day) prevents increases in liver damage, hepatocyte apoptosis, serum levels of alanine transaminase (ALT) and aspartate aminotransferase (AST), and hepatic levels of malondialdehyde (MDA), as well as decreases in the hepatic levels of glutathione (GSH), superoxide dismutase (SOD), and Bax in a mouse model of liver injury induced by the plant lectin concanavalin A .3
This information has been provided by Cayman Chemical
References
1. Zhang, X., Xiong, H., and Liu, L. Effects of taraxasterol on inflammatory responses in lipopolysaccharide-induced RAW 264.7 macrophages. J. Ethnopharmacol. 141(1), 206-211 (2012).
String Representations
InChiKey (Click to copy)
XWMMEBCFHUKHEX-ZJJHUPNDSA-N
InChi (Click to copy)
InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23-,24+,25-,27-,28+,29-,30-/m1/s1
SMILES (Click to copy)
[C@@]12(C)CC[C@@]3([H])C(C)(C)[C@H](CC[C@]3(C)[C@@]1([H])CC[C@]1([H])[C@@]3([H])[C@H](C)C(CC[C@@]3(CC[C@@]21C)C)=C)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
31
Rings
5
Aromatic Rings
0
Rotatable Bonds
0
Van der Waals Molecular Volume
471.91
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
8.31
Molar Refractivity
131.16
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Updated at
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