Compound Detail

CHEMBL514409

HESPERADIN

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

CCS(=O)(=O)Nc1ccc2c(c1)/C(=C(/Nc1ccc(CN3CCCCC3)cc1)c1ccccc1)C(=O)N2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL514409
Name	HESPERADIN
Phase	Preclinical
Structure Type	MOL
InChI Key	GLDSKRNGVVYJAB-DQSJHHFOSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

516.7

MW (Da)

5.37

ALogP

HBA

HBD

90.5

PSA (Å²)

0.35

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C29H32N4O3S
MW	516.67
Aromatic Rings	3
Heavy Atoms	37
NP-Likeness	-1.16

Activity Summary

IC50 16 meas. best 8.52

Kd 12 meas. best 8.3

EC50 8 meas. best 8.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aurora kinase B CHEMBL2185	IC50	8.52	6.92	3.0	6
Aurora kinase B-A CHEMBL2176838	IC50	8.52	8.52	3.0	1
Unchecked CHEMBL612545	Kd	8.3	8.3	5.0	1
Serine/threonine-protein kinase 26 CHEMBL5941	IC50	8.22	8.22	6.0	1
Plasmodium falciparum CHEMBL364	EC50	8.0	7.8825	10.0	4
Protein-tyrosine kinase 2-beta CHEMBL5469	Kd	8.0	8.0	10.0	1
Serine/threonine-protein kinase 24 CHEMBL5082	IC50	8.0	8.0	10.0	1
Aurora kinase A CHEMBL4722	IC50	7.96	7.96	11.0	1
5'-AMP-activated protein kinase catalytic subunit alpha-1 CHEMBL4045	Kd	7.72	7.72	19.0	1
Ribosomal protein S6 kinase alpha-5 CHEMBL4237	Kd	7.51	7.51	31.0	1
Focal adhesion kinase 1 CHEMBL2695	Kd	7.48	7.48	33.0	1
Leukocyte tyrosine kinase receptor CHEMBL5627	Kd	7.28	7.28	52.0	1
Trypanosoma brucei CHEMBL612849	EC50	7.22	7.22	60.0	1
Non-receptor tyrosine-protein kinase TYK2 CHEMBL3553	Kd	7.12	7.12	75.0	1
Proto-oncogene tyrosine-protein kinase ROS CHEMBL5568	Kd	7.11	7.11	77.0	1
Serine/threonine-protein kinase BRSK2 CHEMBL4574	Kd	7.04	7.04	92.0	1
Ribosomal protein S6 kinase alpha-4 CHEMBL3125	Kd	7.03	7.03	94.0	1
Leishmania major CHEMBL612879	EC50	6.92	6.27	120.0	2
Tyrosine-protein kinase Fes/Fps CHEMBL5455	Kd	6.83	6.83	149.0	1
Maternal embryonic leucine zipper kinase CHEMBL4578	IC50	6.65	6.65	225.0	2
Unchecked CHEMBL612545	IC50	6.6	6.6	250.0	1
Influenza A virus CHEMBL613740	EC50	6.55	6.55	280.0	1
Glucose transporter CHEMBL3431938	IC50	5.95	5.95	1114.0	1
Hexose transporter 1 CHEMBL4697	IC50	5.87	5.87	1344.0	1
Solute carrier family 2, facilitated glucose transporter member 1 CHEMBL2535	IC50	5.84	5.84	1434.0	1
Serine/threonine-protein kinase PAK 2 CHEMBL4487	Kd	4.85	4.85	14000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aurora kinase B	IC50	=	3.0	nM	8.52	Inhibition of human Aurora kinase B/INCEP complex expressed in Escherichia coli ...	22920039
Aurora kinase B-A	IC50	=	3.0	nM	8.52	Inhibition of Xenopus laevis Aurora kinase B/INCEP complex using gamma-[32P]ATP ...	22920039
Unchecked	Kd	=	5.0	nM	8.3	Binding affinity to human KHS2	19035792
Serine/threonine-protein kinase 26	IC50	=	6.0	nM	8.22	Inhibition of MST4 (unknown origin)	38422480
Plasmodium falciparum	EC50	=	10.0	nM	8.0	Antiprotozoal activity against Plasmodium falciparum D6 assessed as growth inhib...	24910766
Protein-tyrosine kinase 2-beta	Kd	=	10.0	nM	8.0	Binding affinity to human PYK2	19035792
Plasmodium falciparum	EC50	=	10.0	nM	8.0	Antiprotozoal activity against chloroquine/mefloquine/pyrimethamine-resistant Pl...	24910766
Serine/threonine-protein kinase 24	IC50	=	10.0	nM	8.0	Inhibition of MST3 (unknown origin)	38422480
Aurora kinase A	IC50	=	11.0	nM	7.96	Inhibition of human Aurora kinase A/TPX2 complex using gamma-[32P]ATP incubated ...	22920039
Plasmodium falciparum	EC50	=	14.0	nM	7.85	Antiprotozoal activity against chloroquine-resistant Plasmodium falciparum C2B a...	24910766
5'-AMP-activated protein kinase catalytic subunit alpha-1	Kd	=	19.0	nM	7.72	Binding affinity to human AMPKA1	19035792
Plasmodium falciparum	EC50	=	21.0	nM	7.68	Antiprotozoal activity against chloroquine-resistant Plasmodium falciparum W2 as...	24910766
Ribosomal protein S6 kinase alpha-5	Kd	=	31.0	nM	7.51	Binding affinity to human MSK1	19035792
Focal adhesion kinase 1	Kd	=	33.0	nM	7.48	Binding affinity to human FAK	19035792
Leukocyte tyrosine kinase receptor	Kd	=	52.0	nM	7.28	Binding affinity to human LTK	19035792
Trypanosoma brucei	EC50	=	60.0	nM	7.22	Antiprotozoal activity against Trypanosoma brucei 427 assessed as growth inhibit...	24910766
Non-receptor tyrosine-protein kinase TYK2	Kd	=	75.0	nM	7.12	Binding affinity to human TYK2	19035792
Proto-oncogene tyrosine-protein kinase ROS	Kd	=	77.0	nM	7.11	Binding affinity to human ROS	19035792
Serine/threonine-protein kinase BRSK2	Kd	=	92.0	nM	7.04	Binding affinity to human BRSK2	19035792
Ribosomal protein S6 kinase alpha-4	Kd	=	94.0	nM	7.03	Binding affinity to human MSK2	19035792

Literature References

PubMed	DOI	Target Context	# Activities
19035792	10.1021/jm8011036	Unchecked	9
33691794	10.1186/s13148-021-01037-1	A549	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
20485427	10.1038/nature09107	Plasmodium falciparum	4
24910766	10.1039/c4md00045e	Plasmodium falciparum	4
19035792	10.1021/jm8011036	Ribosomal protein S6 kinase alpha-4	3
19035792	10.1021/jm8011036	Proto-oncogene tyrosine-protein kinase ROS	2
19035792	10.1021/jm8011036	Mitogen-activated protein kinase kinase kinase kinase 4	2
19035792	10.1021/jm8011036	Atypical kinase COQ8B, mitochondrial	2
27519462	10.1016/j.bmc.2016.07.069	Trypanosoma brucei	2
-	10.6019/CHEMBL3433997	Hexose transporter 1	2
-	10.6019/CHEMBL3433997	Glucose transporter	2
19035792	10.1021/jm8011036	Non-receptor tyrosine-protein kinase TYK2	2
19035792	10.1021/jm8011036	Protein-tyrosine kinase 2-beta	2
19035792	10.1021/jm8011036	Focal adhesion kinase 1	2
19035792	10.1021/jm8011036	Leukocyte tyrosine kinase receptor	2
19035792	10.1021/jm8011036	Tyrosine-protein kinase Fes/Fps	2
19035792	10.1021/jm8011036	Serine/threonine-protein kinase BRSK2	2
19035792	10.1021/jm8011036	5'-AMP-activated protein kinase catalytic subunit alpha-1	2
19035792	10.1021/jm8011036	Ribosomal protein S6 kinase alpha-5	2

Data from ChEMBL 36 via Core Engine