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

Classification

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Physalis peruviana (#126903)
Magnoliopsida (#3398)
Isolation of 4 beta-hydroxywithanolide E, a new withanolide from Physalis peruviana L.,
Chem Pharm Bull (Tokyo), 1976
Pubmed ID: 1021295

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

HMDB ID
CHEBI ID
PubChem CID
Cayman ID

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