Compound Detail

CHEMBL478

CHLOROPHENYLPIPERAZINE

🧪 Phase II

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🧪 Phase II

Clc1cccc(N2CCNCC2)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL478
Name	CHLOROPHENYLPIPERAZINE
Phase	Phase II
Structure Type	MOL
InChI Key	VHFVKMTVMIZMIK-UHFFFAOYSA-N

Known Names

1-m-chlorophenyl piperazine metabolite Chlorophenylpiperazine Mcpp

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

196.7

MW (Da)

1.75

ALogP

HBA

HBD

15.3

PSA (Å²)

0.74

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C10H13ClN2
MW	196.68
Aromatic Rings	1
Heavy Atoms	13
NP-Likeness	-1.66

Indications

Alcoholism Cocaine-Related Disorders

Activity Summary

Ki 42 meas. best 8.36

EC50 26 meas. best 8.14

IC50 2 meas. best 5.7

Kd 1 meas. best 7.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	8.36	7.74	4.4	2
5-hydroxytryptamine receptor 2A CHEMBL224	EC50	8.14	6.9533	7.2	9
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	8.1	7.8833	7.9	6
5-hydroxytryptamine receptor 2C CHEMBL225	EC50	8.1	7.625	7.9	10
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	8.0	7.648	10.0	5
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.64	6.7825	23.0	8
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	7.6	7.6	25.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.6	7.2629	25.1	7
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	7.4	7.4	40.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	EC50	7.4	6.8886	39.8	7
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.38	7.38	42.0	1
Serotonin 3 (5-HT3) receptor CHEMBL2094132	Ki	7.21	7.21	62.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Kd	7.0	7.0	100.0	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	6.79	6.655	163.0	2
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	6.63	6.63	236.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.57	6.57	271.0	1
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	6.45	6.45	352.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	5.76	5.7	1748.0	2
Beta-1 adrenergic receptor CHEMBL213	IC50	5.7	5.7	2000.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.21	5.21	6150.0	1
5-hydroxytryptamine receptor 5A CHEMBL3597	Ki	5.06	5.06	8700.0	2
Beta-2 adrenergic receptor CHEMBL2289	IC50	4.75	4.75	18000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	-	-	Homo sapiens
CL	6.1	mL.min-1.kg-1	Homo sapiens
MRT	7.0	hr	Homo sapiens
T1/2	4.7	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 1B	Ki	=	4.4	nM	8.36	Binding affinity at rat 5-hydroxytryptamine 1B receptor by [3H]5-HT displacement...	2565400
5-hydroxytryptamine receptor 2A	EC50	=	7.2	nM	8.14	Agonist activity at serotonin-activated human recombinant 5HT-2A receptor expres...	23537943
5-hydroxytryptamine receptor 2C	EC50	=	7.943	nM	8.1	Agonist activity at human 5HT2C receptor expressed in HEK293 cells assessed as i...	18095642
5-hydroxytryptamine receptor 2C	Ki	=	7.943	nM	8.1	Displacement of [125I]DOI from recombinant human 5-HT2C receptor expressed in HE...	27864071
5-hydroxytryptamine receptor 2C	EC50	=	8.1	nM	8.09	Agonist activity at serotonin-activated human recombinant 5HT-2C receptor expres...	23537943
5-hydroxytryptamine receptor 2C	Ki	=	9.0	nM	8.05	Displacement of [3H]5-HT from human 5HT2C	16257207
5-hydroxytryptamine receptor 2C	Ki	=	9.0	nM	8.05	Affinity for human 5-hydroxytryptamine 2C receptor expressed in mammalian cell l...	15081042
5-hydroxytryptamine receptor 2B	Ki	=	10.0	nM	8.0	Displacement of [125I]DOI from recombinant human 5-HT2B receptor expressed in HE...	27864071
5-hydroxytryptamine receptor 2C	EC50	=	12.59	nM	7.9	Agonist activity at unedited 5-HT2C receptor (unknown origin) expressed in HEK29...	27864071
5-hydroxytryptamine receptor 2C	EC50	=	15.0	nM	7.82	Agonist activity at recombinant human 5-HT2C receptor expressed in HEK293E cells...	28635286
5-hydroxytryptamine receptor 2C	EC50	=	15.0	nM	7.82	Agonist activity at human recombinant 5HT2C receptor expressed in HEK293E cells ...	20022752
5-hydroxytryptamine receptor 2C	EC50	=	15.0	nM	7.82	Activity at human 5HT2C expressed in HEK293E cells assessed as elevation of intr...	17315987
5-hydroxytryptamine receptor 2C	Ki	=	17.0	nM	7.77	Displacement of [125I]DOI from human recombinant 5HT2C expressed in HEK293E cell...	17315987
5-hydroxytryptamine receptor 2C	Ki	=	17.0	nM	7.77	Displacement of [125I]DOI from human recombinant 5HT2C receptor expressed in HEK...	20022752
5-hydroxytryptamine receptor 1A	Ki	=	23.0	nM	7.64	Binding affinity at rat 5-hydroxytryptamine 1A receptor by [3H]WB-4101 displacem...	2565400
5-hydroxytryptamine receptor 2B	Ki	=	24.0	nM	7.62	Displacement of [125I]LSD from human recombinant 5HT2B receptor expressed in HEK...	20022752
5-hydroxytryptamine receptor 2B	Ki	=	24.0	nM	7.62	Displacement of [3H]LSD from human recombinant 5HT2B expressed in HEK293E cells	17315987
5-hydroxytryptamine receptor 2A	Ki	=	25.12	nM	7.6	Displacement of [125I]DOI from recombinant human 5-HT2A receptor expressed in HE...	27864071
Serotonin 1 (5-HT1) receptor	Ki	=	25.0	nM	7.6	Inhibition of [3H]5-HT radioligand binding against 5-hydroxytryptamine 1 recepto...	2565400
5-hydroxytryptamine receptor 2C	EC50	=	26.0	nM	7.58	Functional activity against human 5-hydroxytryptamine 2C receptor expressed in C...	15081042

Literature References

PubMed	DOI	Target Context	# Activities
8410989	10.1021/jm00071a006	ADMET	6
18426954	10.1124/dmd.108.020479	ADMET	4
15081042	10.1016/j.bmcl.2003.05.001	5-hydroxytryptamine receptor 2B	3
20022752	10.1016/j.bmcl.2009.12.014	5-hydroxytryptamine receptor 2C	3
20022752	10.1016/j.bmcl.2009.12.014	5-hydroxytryptamine receptor 2A	3
16257207	10.1016/j.bmcl.2005.10.029	5-hydroxytryptamine receptor 2C	3
27864071	10.1016/j.bmcl.2016.11.016	5-hydroxytryptamine receptor 2B	3
15081042	10.1016/j.bmcl.2003.05.001	5-hydroxytryptamine receptor 2C	3
27864071	10.1016/j.bmcl.2016.11.016	5-hydroxytryptamine receptor 2C	3
15081042	10.1016/j.bmcl.2003.05.001	5-hydroxytryptamine receptor 2A	3
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	3
16257207	10.1016/j.bmcl.2005.10.029	5-hydroxytryptamine receptor 2A	3
20022752	10.1016/j.bmcl.2009.12.014	5-hydroxytryptamine receptor 2B	3
27864071	10.1016/j.bmcl.2016.11.016	5-hydroxytryptamine receptor 2A	3
16257207	10.1016/j.bmcl.2005.10.029	5-hydroxytryptamine receptor 2B	3
19716297	10.1016/j.bmcl.2009.07.136	5-hydroxytryptamine receptor 2C	2
15081042	10.1016/j.bmcl.2003.05.001	Rattus norvegicus	2
2565400	10.1021/jm00125a020	Rattus norvegicus	2
17315987	10.1021/jm0612968	5-hydroxytryptamine receptor 2C	2
19716297	10.1016/j.bmcl.2009.07.136	5-hydroxytryptamine receptor 2A	2

Data from ChEMBL 36 via Core Engine