Structure Database (LMSD)

Common Name
Taraxasterol
Systematic Name
18α,19α-urs-20(30)-en-3β-ol
Synonyms
LM ID
LMPR0106180006
Formula
Exact Mass
Calculate m/z
426.386165
Status
Curated

Classification

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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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