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Details

Stereochemistry ACHIRAL
Molecular Formula C25H22N2O2
Molecular Weight 382.4544
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GSK-650394

SMILES

OC(=O)C1=CC=C(C=C1C2CCCC2)C3=CNC4=NC=C(C=C34)C5=CC=CC=C5

InChI

InChIKey=WVSBGSNVCDAMCF-UHFFFAOYSA-N
InChI=1S/C25H22N2O2/c28-25(29)20-11-10-18(12-21(20)17-8-4-5-9-17)23-15-27-24-22(23)13-19(14-26-24)16-6-2-1-3-7-16/h1-3,6-7,10-15,17H,4-5,8-9H2,(H,26,27)(H,28,29)

HIDE SMILES / InChI
Molecular Formula C25H22N2O2
Molecular Weight 382.4544
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

GSK650394 was synthesized by the CVU Medicinal Chemistry Department at GlaxoSmithKline as an inhibitor of serum- and glucocorticoid-regulated kinases, SGK1 and SGK2. It was shown, that GSK650394 possessed antiproliferative properties against the human prostate carcinoma cell line LNCaP.

Originator

GlaxoSmithKline
197
Curator's Comment: # CVU Medicinal Chemistry Department at GlaxoSmithKline

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Serine/threonine-protein kinase Sgk1
1
Target ID: O00141|||Q5TCN4
Gene ID: 6446.0
Gene Symbol: SGK1
Target Organism: Homo sapiens (Human)
Antagonist
2849
 62.0 nM [IC50]
Serine/threonine-protein kinase Sgk2
1
Target ID: Q9HBY8
Gene ID: 10110.0
Gene Symbol: SGK2
Target Organism: Homo sapiens (Human)
Antagonist
2849
 103.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of nominally selective inhibitors of the kinases PI3K, SGK1 and PKB on the insulin-dependent control of epithelial Na+ absorption.
2010-10
Development of a small-molecule serum- and glucocorticoid-regulated kinase-1 antagonist and its evaluation as a prostate cancer therapeutic.
2008-09-15
Patents

Patents

WO2013126581A1
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
The inhibitory effects of GSK650394 on SGK1 activity were evaluated using cell-based assays. Importantly, GSK650394 is relatively nontoxic, with LC50 values of 41 μmol/L in M-1 cells (68 times its activity IC50) and LC50 >100 μmol/L in HeLa cells in XTT assays, which measure mitochondrial enzymatic activity. GSK650394 was evaluated for its effects on this well-documented SGK1-mediated biological activity, which was measured using an aldosterone-stimulated SCC cellular assay. GSK650394 inhibited SGK1-mediated epithelial transport with an IC50 of 0.6 μmol/L in the SCC assay.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:51:23 GMT 2025
Edited
by admin
on Mon Mar 31 22:51:23 GMT 2025
Record UNII
56887611DJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZOIC ACID, 2-CYCLOPENTYL-4-(5-PHENYL-1H-PYRROLO(2,3-B)PYRIDIN-3-YL)-
Preferred Name English
GSK-650394
Common Name English
Code System Code Type Description
PUBCHEM
25022668
Created by admin on Mon Mar 31 22:51:23 GMT 2025 , Edited by admin on Mon Mar 31 22:51:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID60237532
Created by admin on Mon Mar 31 22:51:23 GMT 2025 , Edited by admin on Mon Mar 31 22:51:23 GMT 2025
PRIMARY
FDA UNII
56887611DJ
Created by admin on Mon Mar 31 22:51:23 GMT 2025 , Edited by admin on Mon Mar 31 22:51:23 GMT 2025
PRIMARY
CAS
890842-28-1
Created by admin on Mon Mar 31 22:51:23 GMT 2025 , Edited by admin on Mon Mar 31 22:51:23 GMT 2025
PRIMARY
Related Record Type Details
Structure of GSK-650394
ACTIVE MOIETY
NIH
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