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SML0428

Sigma-Aldrich

GSK690693

≥98% (HPLC)

Synonym(s):

4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-{[(3S)-3-piperidinylmethyl]oxy}-1H-imidazo[4,5-c]pyridin-4-yl)-2-methyl-3-butyn-2-ol

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About This Item

Empirical Formula (Hill Notation):
C21H27N7O3
CAS Number:
937174-76-0
Molecular Weight:
425.48
MDL number:
MFCD14105605
UNSPSC Code:
12352200
PubChem Substance ID:
329825423
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

CCn1c(nc2c(ncc(OC[C@H]3CCCNC3)c12)C#CC(C)(C)O)-c4nonc4N

InChI

1S/C21H27N7O3/c1-4-28-18-15(30-12-13-6-5-9-23-10-13)11-24-14(7-8-21(2,3)29)16(18)25-20(28)17-19(22)27-31-26-17/h11,13,23,29H,4-6,9-10,12H2,1-3H3,(H2,22,27)/t13-/m0/s1

InChI key

KGPGFQWBCSZGEL-ZDUSSCGKSA-N

Gene Information

human ... AKT1(207) , AKT2(208) , AKT3(10000) , PRKACA(5566) , PRKACB(5567) , PRKACG(5568) , PRKCA(5578) , PRKCB(5579) , PRKCD(5580) , PRKCE(5581) , PRKCG(5582) , PRKCH(5583) , PRKCI(5584) , PRKCQ(5588) , PRKCZ(5590) , PRKD1(5587) , PRKD3(23683)

Application

GSK690693 has been used in western blotting and immunoprecipitations.

Biochem/physiol Actions

4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-{[(3S)-3-piperidinylmethyl]oxy}-1H-imidazo[4,5-c]pyridin-4-yl)-2-methyl-3-butyn-2-ol/GSK690693 is a protein kinase B/AKT inhibitor. GSK690693 can prevent growth and apoptosis in acute lymphoblastic leukemia cell lines.
GSK690693 is an ATP competitive, potent pan-AKT kinase inhibitor with IC50 values of 2, 13, and 9 nM against AKT1, 2, and 3, respectively.

Features and Benefits

This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Masayuki Yamaji et al.
Cancer medicine, 6(11), 2646-2659 (2017-09-30)
Malignant pleural mesothelioma (MPM), an asbestos-related occupational disease, is an aggressive and incurable tumor of the thoracic cavity. Despite recent advances in MPM treatment, overall survival of patients with MPM is very low. Recent studies have implicated that PI3K/Akt signaling
Chengchun Tang et al.
BioMed research international, 2020, 4370832-4370832 (2020-05-29)
Platelet-derived growth factor-BB (PDGF-BB) can induce the proliferation, migration, and phenotypic modulation of vascular smooth muscle cells (VSMCs). We used patch clamp methods to study the effects of PDGF-BB on inward rectifier K+ channel 2.1 (Kir2.1) channels in rat thoracic
N Panupinthu et al.
Oncogene, 33(22), 2846-2856 (2013-07-16)
The Y-box binding protein-1 (YB-1) transcription factor is associated with unfavorable clinical outcomes. However, the mechanisms underlying this association remain to be fully elucidated. We demonstrate that YB-1 phosphorylation, indicative of YB-1 activation, is a powerful marker of outcomes for
Michaella Ben-Shachar et al.
Nutrients, 11(6) (2019-06-27)
Sarcopoterium spinosum (S. spinosum) is a medicinal plant, traditionally used as an antidiabetic remedy. Previous studies demonstrated its beneficial properties in the treatment of insulin resistance. The aim of this study was to further clarify the effect of S. spinosum
AKT inhibitor, GSK690693, induces growth inhibition and apoptosis in acute lymphoblastic leukemia cell lines
Levy D S, et al.
Blood, 113(8), 1723-1729 (2009)
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