4β-Hydroxywithanolide E

Name: 4β-Hydroxywithanolide E
CAS#: 54334-04-2
Chemical Formula: C28H38O8
Exact Mass: 502.2567
Molecular Weight: 502.6
Elemental Analysis: C, 66.91; H, 7.62; O, 25.47

Description: 4β-Hydroxywithanolide E is a withanolide steroidal lactone that has anti-inflammatory and anticancer activities. It inhibits LPS-induced nitric oxide (NO) production and TNF-α-induced NF-κB activity. 4β-Hydroxywithanolide E inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 levels and Akt and STAT1 phosphorylation. 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.

IUPAC/Chemical Name: (4S,4aR,5aR,6aR,6bR,9S,9aS,11aS,11bR)-9-((S)-1-((R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl)-4,6b,9-trihydroxy-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one

InChi Key: UPBUGICUKQIKTJ-KABTZXSUSA-N

InChi Code: 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 Code: O=C1[C@@]2(C)[C@@]([C@H]3C[C@]4([H])[C@]2([H])CC[C@@]5(C)[C@@]4(O)CC[C@@]5(O)[C@@](C)(O)[C@@]6([H])CC(C)=C(C)C(O6)=O)(O3)[C@@H](O)C=C1

Appearance: Solid powder