Compound Detail

CHEMBL25554

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COc1cccc(OC)c1OCCNCC1COc2ccccc2O1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL25554
Phase	Preclinical
Structure Type	MOL
InChI Key	GYSZUJHYXCZAKI-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

345.4

MW (Da)

2.51

ALogP

HBA

HBD

58.2

PSA (Å²)

0.74

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C19H23NO5
MW	345.40
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	-0.20

Activity Summary

Ki 66 meas. best 10.42

Kd 25 meas. best 9.8

IC50 4 meas. best 9.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-1B adrenergic receptor CHEMBL232	Ki	10.42	8.1408	0.0	12
Alpha-1A adrenergic receptor CHEMBL319	Ki	10.1	9.495	0.1	2
Alpha-1A adrenergic receptor CHEMBL229	Ki	9.8	9.4467	0.2	12
Adrenergic receptor alpha CHEMBL2094111	Kd	9.8	9.8	0.2	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	9.6	9.3033	0.3	9
Alpha-1A adrenergic receptor CHEMBL319	Kd	9.51	9.365	0.3	6
Alpha-1A adrenergic receptor CHEMBL4892	Ki	9.46	9.2967	0.3	3
Unchecked CHEMBL612545	Ki	9.27	9.27	0.5	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	9.27	8.665	0.5	2
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	9.26	9.21	0.5	3
Adrenergic receptor alpha CHEMBL2095203	Kd	9.2	7.72	0.6	2
Alpha-2C adrenergic receptor CHEMBL1916	Ki	9.1	9.1	0.8	1
Alpha-1A adrenergic receptor CHEMBL229	IC50	9.0	9.0	1.0	2
Alpha-1D adrenergic receptor CHEMBL326	Ki	8.92	8.56	1.2	2
Adrenergic receptor alpha-1 CHEMBL2094251	Kd	8.9	8.9	1.3	1
Unchecked CHEMBL612545	Kd	8.83	8.83	1.5	1
Alpha-1D adrenergic receptor CHEMBL326	Kd	8.8	8.7	1.6	4
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	8.68	8.68	2.1	5
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	8.57	8.355	2.7	2
Alpha-2A adrenergic receptor CHEMBL1867	Ki	8.46	8.46	3.5	1
Alpha-1B adrenergic receptor CHEMBL315	Kd	8.21	8.195	6.2	4
Alpha-1B adrenergic receptor CHEMBL315	Ki	8.1	7.845	8.0	2
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	7.83	7.4533	14.7	3
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.55	7.55	28.0	1
Alpha-2A adrenergic receptor CHEMBL327	Ki	7.34	7.34	46.0	1
D(3) dopamine receptor CHEMBL3138	Ki	6.97	6.97	107.0	1
D(2) dopamine receptor CHEMBL339	Ki	6.91	6.91	122.8	2
Adrenergic receptor alpha-2 CHEMBL2093864	Kd	6.63	6.51	234.4	2
Alpha-2A adrenergic receptor CHEMBL327	Kd	6.59	6.59	257.0	1
Rattus norvegicus CHEMBL376	Ki	6.2	5.9233	634.0	3
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	6.0	6.0	1000.0	1
Rattus norvegicus CHEMBL376	IC50	5.57	5.34	2691.5	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Alpha-1B adrenergic receptor	Ki	=	0.038	nM	10.42	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1B receptor...	31834797
Alpha-1A adrenergic receptor	Ki	=	0.08	nM	10.1	Overall binding displacement in tissues containing only the Alpha-1A adrenergic ...	7658428
Adrenergic receptor alpha	Kd	=	0.1585	nM	9.8	Antagonist at postsynaptic alpha-adrenergic receptor in rat vas deferens	40029
Alpha-1A adrenergic receptor	Ki	=	0.1585	nM	9.8	Binding affinity was tested on human Alpha-1A adrenergic receptor	9135028
Alpha-1A adrenergic receptor	Ki	=	0.16	nM	9.8	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1A receptor...	31834797
Alpha-1D adrenergic receptor	Ki	=	0.2512	nM	9.6	Binding affinity was tested on human Alpha-1D adrenergic receptor	9135028
Alpha-1A adrenergic receptor	Kd	=	0.309	nM	9.51	Antagonistic affinity tested against isolated Rat Prostatic Vas Deferens Alpha-1...	11931617
Alpha-1A adrenergic receptor	Kd	=	0.309	nM	9.51	Antagonistic activity at ADRA1A in isolated rat prostatic vas deferens	16216506
Alpha-1A adrenergic receptor	Ki	=	0.35	nM	9.46	Binding affinity against Alpha-1A adrenergic receptor from bovine clone	7658428
Alpha-1A adrenergic receptor	Ki	=	0.37	nM	9.43	Binding affinity against Alpha-1A adrenergic receptor from human clone	7658428
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Displacement of [3H]prazosin from human recombinant alpha1A adrenergic receptor ...	23252794
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Displacement of [3H]prazosin from human cloned Alpha-1A adrenergic receptor	10514291
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Antagonistic affinity tested against isolated Human recombinant Thoracic Aorta A...	11931617
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Binding affinity measured in CHO cells expressing human cloned Alpha-1A adrenerg...	14584940
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Affinity constant towards human recombinant Alpha-1A adrenergic receptor using [...	12672251
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Displacement of [3H]prazosin from human adrenergic alpha1A expressed in CHO cell...	20801662
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Binding affinity to adrenergic alpha1A receptor (unknown origin)	-
Alpha-1A adrenergic receptor	Ki	=	0.426	nM	9.37	Binding affinity to adrenergic alpha1A receptor (unknown origin)	-
Alpha-1A adrenergic receptor	Ki	=	0.4266	nM	9.37	Displacement of [3H]prazosin from human cloned alpha1A adrenoceptor expressed in...	18817363
Alpha-1A adrenergic receptor	Kd	=	0.4365	nM	9.36	Activity at adrenergic alpha 1A receptor assessed as antagonism of noradrenaline...	17125266

Literature References

PubMed	DOI	Target Context	# Activities
3746815	10.1021/jm00159a017	Rattus norvegicus	4
16033273	10.1021/jm0408969	Unchecked	3
7658428	10.1021/jm00018a001	Alpha-1A adrenergic receptor	3
7658428	10.1021/jm00018a001	Alpha-1B adrenergic receptor	3
40029	10.1021/jm00195a024	Adrenergic receptor alpha	3
23252794	10.1021/jm301525w	PC-3	3
18817363	10.1021/jm800461k	PC-3	3
11931617	10.1021/jm011066n	Adrenergic receptors; alpha-1 A & B	3
11931617	10.1021/jm011066n	Alpha-1A adrenergic receptor	3
8667368	10.1021/jm960069a	Alpha-1B adrenergic receptor	2
7658428	10.1021/jm00018a001	Alpha-2A adrenergic receptor	2
7658428	10.1021/jm00018a001	Alpha-1D adrenergic receptor	2
8667368	10.1021/jm960069a	Alpha-1A adrenergic receptor	2
12672251	10.1021/jm021078o	Alpha-1B adrenergic receptor	2
12672251	10.1021/jm021078o	Alpha-1A adrenergic receptor	2
10514291	10.1021/jm991065j	Alpha-1D adrenergic receptor	2
10514291	10.1021/jm991065j	Alpha-1A adrenergic receptor	2
12672251	10.1021/jm021078o	Alpha-1D adrenergic receptor	2
8667368	10.1021/jm960069a	Adrenergic receptor alpha-1	2
8667368	10.1021/jm960069a	Adrenergic receptor alpha-2	2

Data from ChEMBL 36 via Core Engine