Compound Detail

CHEMBL27173

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NCCc1c[nH]c2ccc3c(c12)CCCO3

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL27173
Phase	Preclinical
Structure Type	MOL
InChI Key	CRBUBLCOTKWRPR-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

216.3

MW (Da)

1.99

ALogP

HBA

HBD

51.0

PSA (Å²)

0.81

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C13H16N2O
MW	216.28
Aromatic Rings	2
Heavy Atoms	16
NP-Likeness	0.21

Activity Summary

IC50 7 meas. best 8.74

Ki 5 meas. best 9.22

EC50 1 meas. best 6.74

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	9.22	9.22	0.6	1
5-hydroxytryptamine receptor 2A CHEMBL322	IC50	8.74	8.74	1.8	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	8.31	8.31	4.9	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	8.2	8.2	6.3	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.85	7.85	14.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	7.85	6.755	14.0	2
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	7.39	7.39	41.0	1
5-hydroxytryptamine receptor 1D CHEMBL1983	IC50	6.96	6.96	110.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	EC50	6.74	6.74	181.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	6.54	6.54	287.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	6.52	6.52	302.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.21	6.21	610.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	Ki	=	0.6	nM	9.22	In vitro inhibitory constant against [125I]DOI binding to 5-hydroxytryptamine 2A...	12954071
5-hydroxytryptamine receptor 2A	IC50	=	1.8	nM	8.74	In vitro inhibition of [125I]DOI binding to 5-hydroxytryptamine 2A receptor in r...	12954071
5-hydroxytryptamine receptor 2A	Ki	=	4.9	nM	8.31	Inhibitory constant determined against cloned human 5-hydroxytryptamine 2A recep...	12954071
5-hydroxytryptamine receptor 2C	Ki	=	6.3	nM	8.2	Inhibitory constant against cloned human 5-hydroxytryptamine 2C receptor using w...	12954071
Serotonin 2 (5-HT2) receptor	IC50	=	14.0	nM	7.85	Compound was evaluated for binding affinity towards 5-hydroxytryptamine 2 recept...	1433172
5-hydroxytryptamine receptor 2B	Ki	=	14.0	nM	7.85	Inhibitory constant against cloned human 5-hydroxytryptamine 2B receptor using w...	12954071
5-hydroxytryptamine receptor 2C	IC50	=	41.0	nM	7.39	Compound was evaluated for binding affinity towards 5-hydroxytryptamine 1C recep...	1433172
5-hydroxytryptamine receptor 1D	IC50	=	110.0	nM	6.96	Compound was evaluated for binding affinity towards 5-hydroxytryptamine 1D recep...	1433172
5-hydroxytryptamine receptor 2A	EC50	=	181.0	nM	6.74	In vitro relative agonist activity against 5-hydroxytryptamine 2A using PI assay...	12954071
5-hydroxytryptamine receptor 1A	IC50	=	287.0	nM	6.54	In vitro inhibitory concentration required against [3H]8-OH-DPAT binding to clon...	12954071
5-hydroxytryptamine receptor 1A	Ki	=	302.0	nM	6.52	Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) r...	8568799
5-hydroxytryptamine receptor 1A	IC50	=	610.0	nM	6.21	Compound was evaluated for binding affinity towards 5-hydroxytryptamine 1A recep...	1433172
Serotonin 2 (5-HT2) receptor	IC50	=	2200.0	nM	5.66	Compound was evaluated for binding affinity towards 5-hydroxytryptamine 2 recept...	1433172

Literature References

PubMed	DOI	Target Context	# Activities
12954071	10.1021/jm030205t	5-hydroxytryptamine receptor 2A	7
12954071	10.1021/jm030205t	5-hydroxytryptamine receptor 1A	2
1433172	10.1021/jm00098a005	Serotonin 2 (5-HT2) receptor	2
12954071	10.1021/jm030205t	5-hydroxytryptamine receptor 2B	1
12954071	10.1021/jm030205t	5-hydroxytryptamine receptor 2C	1
8568799	10.1021/jm950410b	5-hydroxytryptamine receptor 1A	1
1433172	10.1021/jm00098a005	5-hydroxytryptamine receptor 1A	1
1433172	10.1021/jm00098a005	5-hydroxytryptamine receptor 1D	1
1433172	10.1021/jm00098a005	5-hydroxytryptamine receptor 2C	1

Data from ChEMBL 36 via Core Engine