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
502.25667
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

1. Sang-Ngern, M., Youn, U.J., Park, E.J., et al. Withanolides derived from Physalis peruviana (Poha) with potential anti-inflammatory activity. Bioorg. Med. Chem. Lett. 26(12), 2755-2759 (2016).

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

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Created at
-
Updated at
19th Oct 2020