Compound Detail

CHEMBL134519

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COc1cc(C[C@@H](C)N)c(OC)cc1I

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL134519
Phase	Preclinical
Structure Type	MOL
InChI Key	BGMZUEKZENQUJY-SSDOTTSWSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

321.2

MW (Da)

2.20

ALogP

HBA

HBD

44.5

PSA (Å²)

0.86

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	C11H16INO2
MW	321.16
Aromatic Rings	1
Heavy Atoms	15
NP-Likeness	-0.04

Activity Summary

Ki 15 meas. best 10.0

EC50 9 meas. best 8.56

IC50 4 meas. best 9.68

Kd 1 meas. best 7.63

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	10.0	10.0	0.1	1
5-hydroxytryptamine receptor 2A CHEMBL322	IC50	9.68	9.4733	0.2	3
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	9.19	9.19	0.7	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	9.19	8.68	0.7	2
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	8.66	8.0533	2.2	3
No relevant target CHEMBL2362975	EC50	8.56	8.56	2.7	1
Cynomolgus monkey CHEMBL613847	EC50	8.56	8.56	2.7	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	8.4	8.4	4.0	2
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	8.0	8.0	9.9	3
5-hydroxytryptamine receptor 2B CHEMBL323	EC50	7.92	7.92	11.9	2
5-hydroxytryptamine receptor 2A CHEMBL322	EC50	7.75	7.67	17.8	3
Serotonin (5-HT) receptor CHEMBL2094123	Kd	7.63	7.63	23.4	1
5-hydroxytryptamine receptor 2C CHEMBL324	EC50	7.52	7.52	30.2	2
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	5.64	5.64	2290.0	3
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	5.42	5.42	3843.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	Ki	=	0.1	nM	10.0	In vitro inhibitory constant against [125I]DOI binding to 5-hydroxytryptamine 2A...	12954071
5-hydroxytryptamine receptor 2A	IC50	=	0.21	nM	9.68	Inhibition of [125I]DOI binding to 5HT2A receptor in rat cerebral cortex	16392816
5-hydroxytryptamine receptor 2A	IC50	=	0.4	nM	9.4	In vitro inhibition of [125I]DOI binding to 5-hydroxytryptamine 2A receptor in r...	12954071
5-hydroxytryptamine receptor 2A	IC50	=	0.46	nM	9.34	Displacement of [125I]DOI from 5HT2A receptor in rat cerebral cortex	17419053
5-hydroxytryptamine receptor 2A	Ki	=	0.65	nM	9.19	Displacement of [125I]DOI from cloned human 5HT2A receptor expressed in CHO cell...	16392816
5-hydroxytryptamine receptor 1A	Ki	=	0.65	nM	9.19	Inhibitory constant against cloned human 5-hydroxytryptamine 2A receptor using w...	12954071
5-hydroxytryptamine receptor 2B	Ki	=	2.2	nM	8.66	Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in CHO ...	34467758
Cynomolgus monkey	EC50	=	2.72	nM	8.56	Reduction of intra ocular pressure in cynomolgus monkey at 300 ug	17419053
No relevant target	EC50	=	2.72	nM	8.56	Distribution coefficient, log D at pH 7.4	17419053
5-hydroxytryptamine receptor 2C	Ki	=	4.0	nM	8.4	Inhibitory constant against cloned human 5-hydroxytryptamine 2C receptor using w...	12954071
5-hydroxytryptamine receptor 2C	Ki	=	4.0	nM	8.4	Displacement of [125I]DOI from cloned human 5HT2C receptor expressed in CHO cell...	16392816
5-hydroxytryptamine receptor 2A	Ki	=	6.8	nM	8.17	Displacement of [3H]LSD from human recombinant 5-HT2A receptor expressed in HEK ...	34467758
Serotonin 2 (5-HT2) receptor	Ki	=	10.0	nM	8.0	Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece...	3543362
Serotonin 2 (5-HT2) receptor	Ki	=	10.0	nM	8.0	Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece...	3543362
Serotonin 2 (5-HT2) receptor	Ki	=	9.9	nM	8.0	Displacement of [3H]ketanserin from rat prefrontal cortex 5-hydroxytryptamine 2 ...	3950904
5-hydroxytryptamine receptor 2B	EC50	=	11.9	nM	7.92	Agonist activity at 5HT2B receptor in rat stomach fundus assessed as intracellul...	17419053
5-hydroxytryptamine receptor 2B	EC50	=	11.9	nM	7.92	Activity against 5HT2B receptor in longitudinal stomach fundus strips in wistar ...	16392816
5-hydroxytryptamine receptor 2B	Ki	=	18.0	nM	7.75	Displacement of [125I]DOI from cloned human 5HT2B receptor expressed in CHO cell...	16392816
5-hydroxytryptamine receptor 2B	Ki	=	18.0	nM	7.75	Inhibitory constant against cloned human 5-hydroxytryptamine 2B receptor using w...	12954071
5-hydroxytryptamine receptor 2A	EC50	=	17.8	nM	7.75	Agonist activity at 5HT2A receptor in rat A7r5 cells assessed as intracellular c...	17419053

Literature References

PubMed	DOI	Target Context	# Activities
7143352	10.1021/jm00352a013	Rattus norvegicus	9
16392816	10.1021/jm050663x	MDCK	6
12954071	10.1021/jm030205t	5-hydroxytryptamine receptor 2A	6
17419053	10.1016/j.bmcl.2007.03.073	5-hydroxytryptamine receptor 2A	4
16392816	10.1021/jm050663x	5-hydroxytryptamine receptor 2A	4
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	4
16392816	10.1021/jm050663x	Serotonin 2 (5-HT2) receptor	3
16392816	10.1021/jm050663x	5-hydroxytryptamine receptor 2C	3
15537358	10.1021/jm040082s	Monkey	3
12954071	10.1021/jm030205t	Monkey	3
17419053	10.1016/j.bmcl.2007.03.073	5-hydroxytryptamine receptor 2C	3
12954071	10.1021/jm030205t	5-hydroxytryptamine receptor 1A	3
16392816	10.1021/jm050663x	5-hydroxytryptamine receptor 2B	2
3543362	10.1021/jm00384a001	Serotonin 1 (5-HT1) receptor	2
12954071	10.1021/jm030205t	5-hydroxytryptamine receptor 2C	1
3950904	10.1021/jm00152a005	Serotonin 1 (5-HT1) receptor	1
34467758	10.1021/acs.jmedchem.1c00726	5-hydroxytryptamine receptor 1A	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 2C	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1B	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1A	1

Data from ChEMBL 36 via Core Engine