Compound Detail

CHEMBL274654

ORANTINIB

🧪 Phase III

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🧪 Phase III

Cc1[nH]c(/C=C2\C(=O)Nc3ccccc32)c(C)c1CCC(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL274654
Name	ORANTINIB
Phase	Phase III
Structure Type	MOL
InChI Key	NHFDRBXTEDBWCZ-ZROIWOOFSA-N

Known Names

NSC-702827 Orantinib SU-006668 Su-6668 Su006668 TSU-68

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

310.4

MW (Da)

3.14

ALogP

HBA

HBD

82.2

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem

-tinib

Extended Properties

Molecular Formula	C18H18N2O3
MW	310.35
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	-0.07

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Fibroblast growth factor receptor inhibitor	INHIBITOR	Fibroblast growth factor receptor	✓	✓
Platelet-derived growth factor receptor inhibitor	INHIBITOR	Platelet-derived growth factor receptor	✓	✓
Vascular endothelial growth factor receptor 2 inhibitor	INHIBITOR	Vascular endothelial growth factor receptor 2	✓	✓

Indications

Carcinoma, Hepatocellular Breast Neoplasms Colorectal Neoplasms Kidney Neoplasms Lung Neoplasms Multiple Myeloma Neoplasms Pancreatic Neoplasms Prostatic Neoplasms, Castration-Resistant Stomach Neoplasms

Activity Summary

IC50 31 meas. best 7.55

Kd 31 meas. best 9.52

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Fibroblast growth factor receptor 1 CHEMBL3650	Kd	9.52	9.52	0.3	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Kd	9.1	9.1	0.8	1
TRAF2 and NCK-interacting protein kinase CHEMBL4527	Kd	7.92	7.92	12.0	1
Bone morphogenetic protein receptor type-2 CHEMBL5467	Kd	7.72	7.72	19.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	7.55	7.55	28.0	1
Aurora kinase B CHEMBL2185	IC50	7.46	7.3733	35.0	3
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	7.3	6.704	50.0	5
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	6.87	6.0117	135.0	6
Aurora kinase C CHEMBL3935	IC50	6.68	6.68	210.0	1
Platelet-derived growth factor receptor CHEMBL2096980	IC50	6.52	5.1271	300.0	7
BMP-2-inducible protein kinase CHEMBL4522	Kd	6.52	6.52	303.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	6.5	6.5	316.0	1
Unchecked CHEMBL612545	Kd	6.2	5.975	637.0	2
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	6.13	6.13	744.0	1
Aurora kinase B CHEMBL2185	Kd	6.03	6.03	933.0	1
Uncharacterized protein FLJ45252 CHEMBL4105933	Kd	5.93	5.93	1183.0	1
AP2-associated protein kinase 1 CHEMBL3830	Kd	5.93	5.93	1174.0	1
RNA cytidine acetyltransferase CHEMBL4105935	Kd	5.91	5.91	1240.0	1
Ribosomal protein S6 kinase alpha-4 CHEMBL3125	Kd	5.86	5.86	1388.0	1
Serine/threonine-protein kinase ULK3 CHEMBL5047	Kd	5.84	5.84	1455.0	1
Inhibitor of nuclear factor kappa-B kinase subunit epsilon CHEMBL3529	Kd	5.84	5.84	1430.0	1
Serine/threonine-protein kinase 4 CHEMBL4598	Kd	5.8	5.8	1567.0	1
Fibroblast growth factor receptor 1 CHEMBL3650	IC50	5.74	5.504	1810.0	5
Serine/threonine-protein kinase 3 CHEMBL4708	Kd	5.74	5.74	1809.0	1
Serine/threonine-protein kinase TBK1 CHEMBL5408	Kd	5.7	5.7	1982.0	1
Mitogen-activated protein kinase kinase kinase kinase 1 CHEMBL5749	Kd	5.7	5.7	2015.0	1
Unchecked CHEMBL612545	IC50	5.7	5.7	2000.0	1
Casein kinase II subunit alpha' CHEMBL4070	Kd	5.68	5.68	2103.0	1
Cyclin-G-associated kinase CHEMBL4355	Kd	5.68	5.68	2090.0	1
Mitogen-activated protein kinase kinase kinase kinase 2 CHEMBL5330	Kd	5.64	5.64	2276.0	1
Mitogen-activated protein kinase kinase kinase 11 CHEMBL2708	Kd	5.58	5.58	2660.0	1
Ribosomal protein S6 kinase alpha-1 CHEMBL2553	Kd	5.58	5.58	2647.0	1
Serine/threonine-protein kinase LATS1 CHEMBL6167	Kd	5.52	5.52	3011.0	1
Ribosomal protein S6 kinase alpha-5 CHEMBL4237	Kd	5.51	5.51	3117.0	1
Aurora kinase A CHEMBL4722	Kd	5.49	5.49	3254.0	1
Dual specificity mitogen-activated protein kinase kinase 2 CHEMBL2964	Kd	5.49	5.49	3225.0	1
Dual specificity mitogen-activated protein kinase kinase 1 CHEMBL3587	Kd	5.46	5.46	3426.0	1
MV4-11 CHEMBL613835	IC50	5.41	5.41	3900.0	1
Dual specificity mitogen-activated protein kinase kinase 5 CHEMBL4948	Kd	5.31	5.31	4938.0	1
Tyrosine-protein kinase ZAP-70 CHEMBL2803	IC50	4.55	4.55	28400.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Fibroblast growth factor receptor 1	Kd	=	0.3	nM	9.52	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Receptor-type tyrosine-protein kinase FLT3	Kd	=	0.8	nM	9.1	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
TRAF2 and NCK-interacting protein kinase	Kd	=	12.0	nM	7.92	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Bone morphogenetic protein receptor type-2	Kd	=	19.0	nM	7.72	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Vascular endothelial growth factor receptor 1	IC50	=	28.0	nM	7.55	Inhibition of N-terminal GST-tagged Flt1 using poly(Glu,Tyr) as substrate after ...	22765894
Aurora kinase B	IC50	=	35.0	nM	7.46	Inhibition of Aurora B in the presence of 20uM ATP	17850214
Aurora kinase B	IC50	=	47.0	nM	7.33	Inhibition of Aurora B (unknown origin)	38401190
Aurora kinase B	IC50	=	47.0	nM	7.33	Inhibition of recombinant aurora B (unknown origin)	28918096
Platelet-derived growth factor receptor beta	IC50	=	50.0	nM	7.3	Inhibition of PDGFRbeta	19110422
Platelet-derived growth factor receptor beta	IC50	=	60.0	nM	7.22	Inhibition of Platelet-derived growth factor receptor beta (PDGF-Rbeta)	12646019
Platelet-derived growth factor receptor beta	IC50	=	60.0	nM	7.22	Inhibitory activity against Platelet-derived growth factor receptor beta	10602697
Platelet-derived growth factor receptor beta	IC50	=	100.0	nM	7.0	Inhibition of PDGF-stimulated PDGFRbeta phosphorylation expressed in mouse NIH/3...	20403700
Vascular endothelial growth factor receptor 2	IC50	=	135.0	nM	6.87	Inhibition of N-terminal GST-tagged KDR after 4 hrs by luciferase-luciferin coup...	22765894
Aurora kinase C	IC50	=	210.0	nM	6.68	Inhibition of Aurora C in the presence of 5uM ATP	17850214
Platelet-derived growth factor receptor	IC50	=	300.0	nM	6.52	Inhibition of PDGF-induced BrdU incorporation in 3T3 cells without bovine serum ...	12646019
BMP-2-inducible protein kinase	Kd	=	303.0	nM	6.52	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Proto-oncogene tyrosine-protein kinase receptor Ret	Kd	=	316.0	nM	6.5	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Vascular endothelial growth factor receptor 2	IC50	=	410.0	nM	6.39	Inhibitory activity of compound against VEGF induced cell proliferation	10602697
Unchecked	Kd	=	637.0	nM	6.2	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Vascular endothelial growth factor receptor 2	IC50	=	680.0	nM	6.17	Inhibition of VEGFR2	19110422

Literature References

PubMed	DOI	Target Context	# Activities
29935772	10.1016/j.bmcl.2018.06.026	No relevant target	10
12646019	10.1021/jm0204183	Platelet-derived growth factor receptor	7
29191878	10.1126/science.aan4368	Unchecked	5
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
20014752	10.1021/tx900326k	Hepatotoxicity	3
20403700	10.1016/j.bmc.2010.03.052	B16-F10	3
22370340	10.1016/j.bmc.2012.01.029	COLO 205	3
22739090	10.1016/j.bmc.2012.05.068	B16-F10	3
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
17850214	10.1042/bj20070797	Unchecked	2
17850214	10.1042/bj20070797	Aurora kinase C	2
19110422	10.1016/j.bmcl.2008.12.023	HUVEC	2
17618113	10.1016/j.bmcl.2007.06.058	Fibroblast growth factor receptor 1	2
12646019	10.1021/jm0204183	No relevant target	2
10602697	10.1021/jm9904295	Vascular endothelial growth factor receptor 2	2
29935772	10.1016/j.bmcl.2018.06.026	Receptor-type tyrosine-protein kinase FLT3	2
10602697	10.1021/jm9904295	Epidermal growth factor receptor	2
10602697	10.1021/jm9904295	Platelet-derived growth factor receptor beta	2
10602697	10.1021/jm9904295	Fibroblast growth factor receptor 1	2

Data from ChEMBL 36 via Core Engine