Structure Database (LMSD)
Common Name
4beta-Hydroxywithanolide E
Systematic Name
15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one
Synonyms
LM ID
LMST01160010
Formula
Exact Mass
Calculate m/z
502.256671
Sum Composition
Status
Curated
3D model of 4beta-Hydroxywithanolide E
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
4β-Hydroxywithanolide E is a withanolide steroidal lactone that has been found in P. peruviana and has anti-inflammatory and anticancer activities.1,2,3 It inhibits LPS-induced nitric oxide (NO) production in RAW 264.7 cells and TNF-α-induced NF-κB activity in HEK293 cells (IC50s = 0.32 and 0.04 μM, respectively).1 4β-Hydroxywithanolide E (5 μM) inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 levels and Akt and STAT1 phosphorylation in RAW 264.7 cells.2 It inhibits Wnt signaling in HCT116 and SW480 colorectal cancer cells (IC50s = 1.85 and 2.67 μM, respectively).3 4β-Hydroxywithanolide E inhibits the proliferation of HCT116, SW480, HT-29, and LoVo cells (IC50s = 0.24-0.51 μM). It halts the cell cycle at the G0/G1 phase in HCT116 and HT-29 cells and induces apoptosis in HCT116 and SW480 cells in a concentration-dependent manner. 4β-Hydroxywithanolide E (10 mg/kg per day for 14 days) reduces tumor growth in an HCT116 mouse xenograft model.
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
UPBUGICUKQIKTJ-KABTZXSUSA-N
InChi (Click to copy)
InChI=1S/C28H38O8/c1-14-12-20(35-22(31)15(14)2)25(5,32)27(34)11-10-26(33)17-13-21-28(36-21)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30,32-34H,8-13H2,1-5H3/t16-,17+,19-,20+,21+,23-,24-,25-,26+,27-,28+/m0/s1
SMILES (Click to copy)
C1(=O)C=C[C@H](O)[C@@]23O[C@@H]2C[C@@]2([H])[C@]4(O)CC[C@@](O)([C@](O)(C)[C@]5([H])OC(=O)C(C)=C(C)C5)[C@@]4(C)CC[C@]2([H])[C@@]13C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
36
Rings
6
Aromatic Rings
0
Rotatable Bonds
2
Van der Waals Molecular Volume
478.56
Topological Polar Surface Area
138.89
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
8
logP
3.73
Molar Refractivity
131.02
Admin
Created at
-
Updated at
19th Oct 2020