Compound Detail

CHEMBL6616

Enter ChEMBL ID:

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

COc1cc(CC(C)N)c(OC)cc1I

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL6616
Phase	Preclinical
Structure Type	MOL
InChI Key	BGMZUEKZENQUJY-UHFFFAOYSA-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 30 meas. best 9.55

IC50 9 meas. best 8.82

EC50 8 meas. best 8.2

Kd 2 meas. best 7.49

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	9.55	8.0856	0.3	9
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	9.32	9.03	0.5	2
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	9.15	8.1967	0.7	3
Serotonin receptor 2a and 2c (5HT2A and 5HT2C) CHEMBL2111383	Ki	9.15	8.4667	0.7	3
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	9.12	8.5638	0.8	8
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	8.82	8.5125	1.5	8
5-hydroxytryptamine receptor 2A CHEMBL224	EC50	8.2	8.2	6.3	1
5-hydroxytryptamine receptor 2B CHEMBL1833	EC50	8.15	7.96	7.0	4
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	7.72	7.6333	19.0	3
5-hydroxytryptamine receptor 2C CHEMBL324	Ki	7.52	7.52	30.0	1
Serotonin (5-HT) receptor CHEMBL2094123	Kd	7.49	7.49	32.4	1
5-hydroxytryptamine receptor 2C CHEMBL225	EC50	7.34	7.34	45.7	1
5-hydroxytryptamine receptor 2A CHEMBL322	EC50	7.24	7.24	57.0	1
5-hydroxytryptamine receptor 2C CHEMBL324	EC50	6.75	6.75	178.0	1
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	6.04	6.04	920.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Kd	5.3	5.3	5011.9	1
Amine oxidase [flavin-containing] A CHEMBL3358	IC50	4.36	4.36	44000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	Ki	=	0.28	nM	9.55	Binding affinity to human [125I]DOI-labeled 5-HT2A receptor expressed in HEK293 ...	38593423
5-hydroxytryptamine receptor 2A	Ki	=	0.46	nM	9.34	Binding activity against cloned human 5-hydroxytryptamine 2A receptor using [125...	9857084
5-hydroxytryptamine receptor 2C	Ki	=	0.48	nM	9.32	Binding affinity to human [125I]DOI-labeled 5-HT2C receptor expressed in HEK293 ...	38593423
5-hydroxytryptamine receptor 2A	Ki	=	0.7	nM	9.15	Displacement of [125I]DOI from recombinant human 5HT2A expressed in Syrian hamst...	28244748
Serotonin receptor 2a and 2c (5HT2A and 5HT2C)	Ki	=	0.7	nM	9.15	Binding affinity at [3H]DOB labeled sites of 5-hydroxytryptamine 2 receptor dete...	3336031
5-hydroxytryptamine receptor 2A	Ki	=	0.7	nM	9.15	Displacement of [3H]DOB from 5HT2A in Sprague-Dawley rat cortex membranes measur...	28244748
5-hydroxytryptamine receptor 2B	Ki	=	0.75	nM	9.12	Binding affinity to 5HT2B receptor (unknown origin) assessed as inhibition const...	28849908
5-hydroxytryptamine receptor 2A	Ki	=	0.92	nM	9.04	Displacement of [3H]ketanserin from 5HT2A receptor expressed in NIH3T3 cells	18847250
5-hydroxytryptamine receptor 2B	Ki	=	1.5	nM	8.82	Binding affinity to human [125I]DOI-labeled 5-HT2B receptor expressed in CHO cel...	38593423
5-hydroxytryptamine receptor 2B	IC50	=	1.5	nM	8.82	Inhibition of 5HT2B (unknown origin)	28849908
5-hydroxytryptamine receptor 2B	Ki	=	1.6	nM	8.8	Displacement of [125I](+/-)DOI from human recombinant 5-HT2B receptor expressed ...	27997171
5-hydroxytryptamine receptor 2C	Ki	=	1.82	nM	8.74	Binding activity against cloned human 5-hydroxytryptamine 2C receptor using [125...	9857084
5-hydroxytryptamine receptor 2B	Ki	=	2.0	nM	8.7	Binding affinity to human 5-HT2B receptor by radioligand displacement assay	23466604
5-hydroxytryptamine receptor 2B	Ki	=	2.0	nM	8.7	Displacement of [125I](+/-)-DOI from human 5HT2B receptor	21726069
5-hydroxytryptamine receptor 2B	IC50	=	2.5	nM	8.6	Displacement of [125I]DOI from human recombinant 5HT2B receptor expressed in CHO...	27876250
5-hydroxytryptamine receptor 2B	IC50	=	2.5	nM	8.6	Displacement of [125I](+/-)DOI from human recombinant 5-HT2B receptor expressed ...	26988801
Serotonin receptor 2a and 2c (5HT2A and 5HT2C)	Ki	=	2.8	nM	8.55	Binding affinity at 5-hydroxytryptamine 2 receptor determined using [125I]- DOI ...	3336031
5-hydroxytryptamine receptor 2B	Ki	=	2.9	nM	8.54	Binding affinity to 5HT2B (unknown origin) assessed as inhibition constant	28849908
5-hydroxytryptamine receptor 2B	IC50	=	3.2	nM	8.49	Displacement of [125I](+/-)DOI from human recombinant 5-HT2B receptor expressed ...	27997171
5-hydroxytryptamine receptor 2B	IC50	=	3.2	nM	8.49	Binding affinity to human 5-HT2B receptor by radioligand displacement assay	23582449

Literature References

PubMed	DOI	Target Context	# Activities
6611416	10.1021/jm00374a023	Rattus norvegicus	30
3950904	10.1021/jm00152a005	Rattus norvegicus	10
7143352	10.1021/jm00352a013	Rattus norvegicus	9
-	10.1016/S0960-894X(97)00291-6	Rattus norvegicus	9
10090793	10.1021/jm980692q	Rattus norvegicus	6
10514296	10.1021/jm990325u	Rattus norvegicus	5
7996545	10.1021/jm00051a011	Rattus norvegicus	5
38593423	10.1021/acs.jmedchem.3c01961	5-hydroxytryptamine receptor 2B	5
18468904	10.1016/j.bmc.2008.04.050	5-hydroxytryptamine receptor 2A	4
28849908	10.1021/acschembio.7b00481	5-hydroxytryptamine receptor 2B	4
3336031	10.1021/jm00396a003	Serotonin receptor 2a and 2c (5HT2A and 5HT2C)	4
28244748	10.1021/acs.jmedchem.7b00085	5-hydroxytryptamine receptor 2A	3
38593423	10.1021/acs.jmedchem.3c01961	5-hydroxytryptamine receptor 2C	3
25583099	10.1016/j.bmc.2014.12.011	5-hydroxytryptamine receptor 2C	2
23466604	10.1016/j.ejmech.2013.01.044	5-hydroxytryptamine receptor 2B	2
18983139	10.1021/jm8007618	5-hydroxytryptamine receptor 2B	2
1542100	10.1021/jm00082a014	Serotonin 2 (5-HT2) receptor	2
25583099	10.1016/j.bmc.2014.12.011	5-hydroxytryptamine receptor 2A	2
7996545	10.1021/jm00051a011	5-hydroxytryptamine receptor 2A	2
7996545	10.1021/jm00051a011	5-hydroxytryptamine receptor 2C	2

Data from ChEMBL 36 via Core Engine