Compound Detail

CHEMBL1236962

OMIPALISIB

🧪 Phase II

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🧪 Phase II

COc1ncc(-c2ccc3nccc(-c4ccnnc4)c3c2)cc1NS(=O)(=O)c1ccc(F)cc1F

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1236962
Name	OMIPALISIB
Phase	Phase II
Structure Type	MOL
InChI Key	CGBJSGAELGCMKE-UHFFFAOYSA-N

Known Names

Gsk-2126458 GSK2126458 Omipalisib

Targets

107

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

505.5

MW (Da)

4.84

ALogP

HBA

HBD

107.0

PSA (Å²)

0.35

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

USAN Stem	-lisib
USAN Year	2014

Extended Properties

Molecular Formula	C25H17F2N5O3S
MW	505.51
Aromatic Rings	5
Heavy Atoms	36
NP-Likeness	-1.41

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
PI3-kinase class I inhibitor	INHIBITOR	PI3-kinase class I	✓	✓
Serine/threonine-protein kinase mTOR inhibitor	INHIBITOR	Serine/threonine-protein kinase mTOR	✓	✓

Indications

Idiopathic Pulmonary Fibrosis Neoplasms Neoplasms

Activity Summary

IC50 64 meas. best 10.72

Ki 33 meas. best 10.72

EC50 8 meas. best 10.4

Kd 2 meas. best 5.86

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	Ki	10.72	10.715	0.0	4
PI3-kinase p110-alpha/p85-alpha CHEMBL2111367	IC50	10.72	10.72	0.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	IC50	10.72	9.5931	0.0	13
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	Ki	10.7	10.6467	0.0	3
Unchecked CHEMBL612545	Ki	10.7	10.11	0.0	2
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	Ki	10.7	10.052	0.0	5
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform CHEMBL3267	IC50	10.62	9.3886	0.0	7
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	EC50	10.4	10.4	0.0	1
Unchecked CHEMBL612545	IC50	10.4	9.49	0.0	5
PI3-kinase p110-alpha/p85-alpha CHEMBL2111367	Ki	10.22	10.22	0.1	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	IC50	10.22	9.1529	0.1	7
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform CHEMBL3267	Ki	10.22	9.9875	0.1	4
PI3-kinase p110-delta/p85-alpha CHEMBL2111432	Ki	10.15	10.15	0.1	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	IC50	9.89	9.2329	0.1	7
mTORC1 CHEMBL4296661	Ki	9.74	9.74	0.2	4
mTORC2 CHEMBL4523999	IC50	9.74	9.74	0.2	1
Serine/threonine-protein kinase mTOR CHEMBL2842	IC50	9.74	9.3186	0.2	7
Unchecked CHEMBL612545	EC50	9.68	9.264	0.2	5
DNA-dependent protein kinase catalytic subunit CHEMBL3142	IC50	9.55	9.55	0.3	1
mTORC2 CHEMBL4523999	Ki	9.52	9.52	0.3	3
PI3K p110 beta/p85 alpha CHEMBL3038510	Ki	9.28	9.28	0.5	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	EC50	8.87	8.87	1.3	1
BT-474 CHEMBL614529	IC50	8.62	8.62	2.4	1
T47D CHEMBL614361	IC50	8.52	8.52	3.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.0	7.186	10.0	5
SARS-CoV-2 CHEMBL4303835	IC50	7.85	7.85	14.0	1
MCF7 CHEMBL387	IC50	7.52	7.52	30.0	1
Trypanosoma brucei CHEMBL612849	IC50	6.96	6.96	111.0	1
MDA-MB-231 CHEMBL400	IC50	6.89	6.89	130.0	1
HCT-116 CHEMBL394	IC50	6.85	6.85	140.0	1
Phosphatidylinositol 3-kinase catalytic subunit type 3 CHEMBL1075165	EC50	6.44	6.44	364.0	1
A549 CHEMBL392	IC50	6.22	6.145	600.0	2
Phosphatidylinositol 5-phosphate 4-kinase type-2 gamma CHEMBL1770034	Kd	5.86	5.86	1372.0	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	IC50	5.75	5.75	1770.0	1
Interleukin-1 receptor-associated kinase 3 CHEMBL5081	Kd	5.52	5.52	3033.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	10.0	mL.min-1.kg-1	Mus musculus
CL	2.3	mL.min-1.kg-1	Rattus norvegicus
CL	5.8	mL.min-1.kg-1	Canis lupus familiaris
CL	3.6	mL.min-1.kg-1	Macaca mulatta
F	100.0	%	Mus musculus
F	81.0	%	Rattus norvegicus
F	80.0	%	Canis lupus familiaris
F	49.0	%	Macaca mulatta
T1/2	2.1	hr	Mus musculus
T1/2	6.2	hr	Rattus norvegicus
T1/2	1.3	hr	Canis lupus familiaris
T1/2	3.5	hr	Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Ki	=	0.019	nM	10.72	Affinity Biochemical interaction (HTRF-based inhibition assay) EUB0000691a PIK3C...	-
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Ki	=	0.019	nM	10.72	Binding affinity to p110 alpha (unknown origin) assessed as inhibition constant ...	24900173
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Ki	=	0.019	nM	10.72	Inhibition of PI3K alpha (unknown origin) by PIP3 production detection based flu...	28719179
PI3-kinase p110-alpha/p85-alpha	IC50	=	0.019	nM	10.72	Competitive inhibition of human PI3K p110alpha/p85alpha using PIP2 as substrate ...	28571824
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	0.019	nM	10.72	Inhibition of PI3Kalpha (unknown origin)	37669595
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Ki	=	0.02	nM	10.7	Inhibition of P13Kalpha (unknown origin) assessed as inhibition constant	36462440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform	Ki	=	0.02	nM	10.7	Inhibition of P13Kbeta (unknown origin) assessed as inhibition constant	36462440
Unchecked	Ki	=	0.02	nM	10.7	Inhibition of P13Kgamma (unknown origin) assessed as inhibition constant	36462440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform	Ki	=	0.02	nM	10.7	Inhibition of P13Kdelta (unknown origin) assessed as inhibition constant	36462440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform	Ki	=	0.024	nM	10.62	Binding affinity to p110 delta (unknown origin) assessed as inhibition constant ...	24900173
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	IC50	=	0.024	nM	10.62	Inhibition of PI3Kgamma (unknown origin)	37669595
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform	Ki	=	0.024	nM	10.62	Affinity Biochemical interaction (HTRF-based inhibition assay) EUB0000691a PIK3C...	-
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	0.04	nM	10.4	Inhibition of PI3Kalpha (unknown origin) by kinase profiling assay	37683364
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	0.04	nM	10.4	Inhibition of PI3Kalpha (unknown origin) using PIP2 as substrate preincubated fo...	24900173
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	EC50	=	0.04	nM	10.4	Inhibition of PI3K alpha (unknown origin) by PIP3 production detection based flu...	28719179
Unchecked	IC50	=	0.04	nM	10.4	Inhibition of mTORC1 (unknown origin)	34894440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	0.04	nM	10.4	Inhibition of PI3Kalpha (unknown origin)	-
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	Ki	=	0.06	nM	10.22	Binding affinity to p110 gamma (unknown origin) assessed as inhibition constant ...	24900173
PI3-kinase p110-alpha/p85-alpha	Ki	=	0.06	nM	10.22	Inhibition of human p110alpha/p85alpha using PIP2 as substrate in presence of AT...	33360802
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	Ki	=	0.06	nM	10.22	Affinity Biochemical interaction (HTRF-based inhibition assay) EUB0000691a PIK3C...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	Fibroblast	345
-	10.6019/CHEMBL4689842	HEK-293T	344
-	10.6019/CHEMBL4689842	U2OS	344
24900173	10.1021/ml900028r	ADMET	26
-	10.6019/CHEMBL5674860	Colon cancer organoid	12
27448924	10.1016/j.ejmech.2016.06.030	NON-PROTEIN TARGET	12
-	10.6019/CHEMBL5724558	Colon cancer organoid	12
33360802	10.1016/j.ejmech.2020.113109	Unchecked	9
24900173	10.1021/ml900028r	BT-474	8
24900173	10.1021/ml900028r	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	8
-	10.6019/CHEMBL5608141	Colon cancer organoid	6
27448924	10.1016/j.ejmech.2016.06.030	Mus musculus	6
29191878	10.1126/science.aan4368	Unchecked	5
24900173	10.1021/ml900028r	Unchecked	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
33561608	10.1016/j.ejmech.2021.113249	Serine/threonine-protein kinase mTOR	3
28719179	10.1021/acs.biochem.7b00413	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform	3
27519462	10.1016/j.bmc.2016.07.069	Trypanosoma brucei	3
-	10.1039/C2MD20044A	Unchecked	3
34795869	10.1021/acsmedchemlett.1c00412	Serine/threonine-protein kinase PIM	2

Data from ChEMBL 36 via Core Engine