Compound Detail

CHEMBL281350

SB-224289

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Cc1nc(-c2ccc(-c3ccc(C(=O)N4CCc5cc6c(cc54)C4(CCN(C)CC4)CO6)cc3)c(C)c2)no1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL281350
Name	SB-224289
Phase	Preclinical
Structure Type	MOL
InChI Key	ATQMRMGXINTJHV-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

520.6

MW (Da)

5.58

ALogP

HBA

HBD

71.7

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	C32H32N4O3
MW	520.63
Aromatic Rings	4
Heavy Atoms	39
NP-Likeness	-0.89

Activity Summary

Ki 23 meas. best 8.56

IC50 9 meas. best 8.7

Kd 1 meas. best 7.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 1B CHEMBL3459	IC50	8.7	8.7	2.0	1
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	8.56	8.19	2.8	4
Unchecked CHEMBL612545	Kd	7.4	7.4	39.8	1
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	6.58	6.4367	260.0	3
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	6.46	6.46	344.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.43	6.43	369.4	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	6.3	6.3	502.1	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.2	6.135	631.0	2
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	6.03	6.03	926.1	1
D(1B) dopamine receptor CHEMBL1850	Ki	5.97	5.97	1077.8	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.93	5.93	1180.6	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	5.9	5.9	1263.9	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.8	5.775	1584.9	2
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.76	5.76	1729.6	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	5.68	5.68	2106.2	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	5.66	5.66	2172.4	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.61	5.61	2431.1	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	5.47	5.47	3422.5	1
Apelin receptor CHEMBL1628481	IC50	5.44	5.44	3632.4	1
N-formyl peptide receptor 3 CHEMBL5646	IC50	5.42	5.42	3838.1	1
Psychosine receptor CHEMBL3714081	IC50	5.39	5.39	4058.0	1
fMet-Leu-Phe receptor CHEMBL3359	IC50	5.37	5.37	4245.5	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.36	5.36	4339.6	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	5.34	5.34	4581.9	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	5.33	5.33	4700.0	1
G-protein coupled receptor 183 CHEMBL3259470	IC50	5.19	5.19	6499.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 1B	IC50	=	2.0	nM	8.7	Inhibition affinity against 5-HT-1B receptor in rat frontal cortex using radio b...	10669578
5-hydroxytryptamine receptor 1B	Ki	=	2.777	nM	8.56	PDSP Secondary Binding target: HTR1B - Compounds are tested at 10 uM concentrati...	-
5-hydroxytryptamine receptor 1B	Ki	=	6.31	nM	8.2	Binding affinity for human 5-hydroxytryptamine 1B receptor	9548813
5-hydroxytryptamine receptor 1B	Ki	=	10.0	nM	8.0	Affinity for 5-hydroxytryptamine 1B receptor subtype	-
5-hydroxytryptamine receptor 1B	Ki	=	10.0	nM	8.0	In vitro binding affinity towards cloned human 5-HT1B receptor using [3H]5-carbo...	16143528
Unchecked	Kd	=	39.81	nM	7.4	pA2 value for the effect in RSV model.	10669578
5-hydroxytryptamine receptor 1D	Ki	=	260.0	nM	6.58	Affinity for 5-hydroxytryptamine 1D receptor subtype	-
Muscarinic acetylcholine receptor M5	Ki	=	344.0	nM	6.46	PDSP Secondary Binding target: CHRM5 - Compounds are tested at 10 uM concentrati...	-
5-hydroxytryptamine receptor 1D	Ki	=	367.88	nM	6.43	PDSP Secondary Binding target: HTR1D - Compounds are tested at 10 uM concentrati...	-
D(1A) dopamine receptor	Ki	=	369.36	nM	6.43	PDSP Secondary Binding target: DRD1 - Compounds are tested at 10 uM concentratio...	-
Sigma intracellular receptor 2	Ki	=	502.11	nM	6.3	PDSP Secondary Binding target: TMEM97 - Compounds are tested at 10 uM concentrat...	-
5-hydroxytryptamine receptor 1D	Ki	=	501.19	nM	6.3	Binding affinity for human 5-hydroxytryptamine 1D receptor	9548813
5-hydroxytryptamine receptor 2C	Ki	=	630.96	nM	6.2	Compound was tested for binding affinity against human 5-hydroxytryptamine 2C re...	9548813
5-hydroxytryptamine receptor 2C	Ki	=	859.31	nM	6.07	PDSP Secondary Binding target: HTR2C - Compounds are tested at 10 uM concentrati...	-
Muscarinic acetylcholine receptor M3	Ki	=	926.08	nM	6.03	PDSP Secondary Binding target: CHRM3 - Compounds are tested at 10 uM concentrati...	-
D(1B) dopamine receptor	Ki	=	1077.83	nM	5.97	PDSP Secondary Binding target: DRD5 - Compounds are tested at 10 uM concentratio...	-
Sodium-dependent dopamine transporter	Ki	=	1180.59	nM	5.93	PDSP Secondary Binding target: SLC6A3 - Compounds are tested at 10 uM concentrat...	-
Muscarinic acetylcholine receptor M1	Ki	=	1263.86	nM	5.9	PDSP Secondary Binding target: CHRM1 - Compounds are tested at 10 uM concentrati...	-
5-hydroxytryptamine receptor 2A	Ki	=	1584.89	nM	5.8	Binding affinity for human 5-hydroxytryptamine 2A receptor	9548813
Sodium-dependent noradrenaline transporter	Ki	=	1729.62	nM	5.76	PDSP Secondary Binding target: SLC6A2 - Compounds are tested at 10 uM concentrat...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	Fibroblast	345
-	10.6019/CHEMBL4689842	HEK-293T	345
-	10.6019/CHEMBL4689842	U2OS	343
9548813	10.1021/jm970457s	Cavia porcellus	15
9548813	10.1021/jm970457s	Serotonin 1 receptors; 5-HT1B & 5-HT1D	12
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	5
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	5
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
-	10.6019/CHEMBL5209801	Apelin receptor	5
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	5
-	10.6019/CHEMBL5209801	C5a anaphylatoxin chemotactic receptor 1	5
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	5
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	5
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	5
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5
9548813	10.1021/jm970457s	5-hydroxytryptamine receptor 1B	3
-	10.6019/CHEMBL5209801	G-protein coupled receptor 35	2
-	10.1016/S0960-894X(97)10164-0	5-hydroxytryptamine receptor 1B	2

Data from ChEMBL 36 via Core Engine