Compound Detail

CHEMBL267930

SPIPERONE

🧪 Phase II

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🧪 Phase II

O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL267930
Name	SPIPERONE
Phase	Phase II
Structure Type	MOL
InChI Key	DKGZKTPJOSAWFA-UHFFFAOYSA-N

Known Names

Espiperona NSC-170983 R 5147 R-5147 Spiperone Spiropitan

Targets

127

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

395.5

MW (Da)

3.22

ALogP

HBA

HBD

52.6

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

USAN Stem	-perone
USAN Year	1966

Extended Properties

Molecular Formula	C23H26FN3O2
MW	395.48
Aromatic Rings	2
Heavy Atoms	29
NP-Likeness	-0.84

Activity Summary

Ki 95 meas. best 10.82

IC50 27 meas. best 10.22

Kd 3 meas. best 9.8

EC50 2 meas. best 8.85

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
D(2) dopamine receptor CHEMBL339	Ki	10.82	9.88	0.0	7
Rattus norvegicus CHEMBL376	Ki	10.7	8.982	0.0	5
D(2) dopamine receptor CHEMBL339	IC50	10.22	10.22	0.1	1
D(2) dopamine receptor CHEMBL217	Ki	10.22	9.7025	0.1	12
D(3) dopamine receptor CHEMBL234	Ki	9.92	9.4713	0.1	8
D(2) dopamine receptor CHEMBL217	Kd	9.8	9.8	0.2	1
D(4) dopamine receptor CHEMBL219	Ki	9.7	9.346	0.2	5
D(2) dopamine receptor CHEMBL217	IC50	9.6	9.048	0.2	5
D(3) dopamine receptor CHEMBL234	IC50	9.44	7.8267	0.4	3
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	9.35	9.07	0.5	5
D(4) dopamine receptor CHEMBL219	IC50	9.3	8.9033	0.5	3
Serotonin receptor 2a and 2c (5HT2A and 5HT2C) CHEMBL2111383	Ki	9.3	8.9867	0.5	3
Unchecked CHEMBL612545	Ki	9.1	8.69	0.8	2
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	9.0	8.87	1.0	2
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	8.96	8.6683	1.1	6
Alpha-1B adrenergic receptor CHEMBL315	Ki	8.89	8.89	1.3	1
D(2) dopamine receptor CHEMBL217	EC50	8.85	8.85	1.4	1
Beta-casein CHEMBL2210	Ki	8.81	8.81	1.5	1
Dopamine receptor CHEMBL2093868	Ki	8.7	8.7	2.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	8.67	8.67	2.1	1
Rattus norvegicus CHEMBL376	IC50	8.62	8.365	2.4	2
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	8.25	8.25	5.7	2
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	8.16	8.16	6.9	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	8.15	8.15	7.1	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	8.14	7.78	7.2	2
Alpha-1A adrenergic receptor CHEMBL229	Ki	8.1	8.1	7.9	1
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	8.0	7.8	9.9	3
Alpha-1A adrenergic receptor CHEMBL4892	Ki	7.87	7.87	13.5	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.76	7.76	17.2	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.7	7.116	19.9	5
Alpha-1D adrenergic receptor CHEMBL326	Ki	7.66	7.66	21.9	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.6	7.215	25.1	6
5-hydroxytryptamine receptor 1A CHEMBL214	Kd	7.4	7.4	39.8	1
5-hydroxytryptamine receptor 7 CHEMBL4764	Ki	7.2	7.2	63.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.91	6.91	123.0	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	6.87	6.87	134.9	1
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	6.8	6.8	160.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.49	6.49	323.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	6.22	6.22	600.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.2	6.07	631.0	2
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	6.02	6.02	955.0	1
5-hydroxytryptamine receptor 2C CHEMBL324	Ki	6.0	5.9	1000.0	2
5-hydroxytryptamine receptor 1B CHEMBL3459	IC50	6.0	6.0	1000.0	1
Vesicular acetylcholine transporter CHEMBL2125	Ki	5.99	5.99	1033.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.9	5.9	1258.9	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	5.8	5.8	1595.0	2
Plasmodium falciparum CHEMBL364	IC50	5.75	5.75	1760.0	1
HLA class I histocompatibility antigen, A alpha chain CHEMBL2632	Kd	5.6	5.6	2500.0	1
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	5.32	5.32	4800.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	4.65	4.65	22350.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Fu	0.66	-	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(2) dopamine receptor	Ki	=	0.015	nM	10.82	Competitive binding assay against Dopamine receptor D2 in rat striatal membranes...	2136916
Rattus norvegicus	Ki	=	0.02	nM	10.7	Inhibition constant on radiolabeled [125 I] FIDA1 binding to rat striatal membra...	8093734
Rattus norvegicus	Ki	=	0.03	nM	10.52	Inhibition constant on radiolabeled [125 I] FIDA2 binding to rat striatal membra...	8093734
D(2) dopamine receptor	Ki	=	0.045	nM	10.35	Binding affinity of compound against Dopamine receptor D2 binding site using rad...	2569041
D(2) dopamine receptor	Ki	=	0.058	nM	10.24	Displacement of [3H]spiperone from dopamine receptor D2	1531364
D(2) dopamine receptor	IC50	=	0.06	nM	10.22	In vitro inhibition of [3H]spiroperidol binding to rat Dopamine D2 receptors.	9986719
D(2) dopamine receptor	Ki	=	0.06	nM	10.22	Displacement of [125I]IABN from recombinant human D2 long receptor stably expres...	31021617
D(2) dopamine receptor	Ki	=	0.06	nM	10.22	Displacement of [125I]ABN from human dopamine D2 long receptor expressed in HEK2...	29125762
D(2) dopamine receptor	Ki	=	0.06	nM	10.22	Binding affinity against dopamine receptor D2 by using [3H]spiperone as radiolig...	1956042
D(2) dopamine receptor	Ki	=	0.089	nM	10.05	Displacement of [3H]Spiperone from human recombinant dopamine D2S receptor expre...	23403082
D(2) dopamine receptor	Ki	=	0.1	nM	10.0	Displacement of [3H]sulpiride from dopamine D2 receptor	8496700
D(3) dopamine receptor	Ki	=	0.12	nM	9.92	Displacement of [3H]Spiperone from human recombinant dopamine D3 receptor expres...	23403082
D(2) dopamine receptor	Ki	=	0.12	nM	9.92	Binding affinity for human dopamine receptor D2 long	15689154
D(2) dopamine receptor	Ki	=	0.149	nM	9.83	Inhibitory constant against binding of [125I]- IBZM to rat striatal membrane	2966245
D(2) dopamine receptor	Kd	=	0.16	nM	9.8	Binding affinity to dopamine D2 receptor in human brain caudate nucleus	27364609
D(2) dopamine receptor	Ki	=	0.2	nM	9.7	Tested for binding affinity against dopamine receptor D2	8355253
D(4) dopamine receptor	Ki	=	0.2	nM	9.7	Displacement of [3H]Spiperone from human recombinant dopamine D4 receptor expres...	23403082
D(3) dopamine receptor	Ki	=	0.25	nM	9.6	Binding affinity for human dopamine receptor D3	15689154
D(3) dopamine receptor	Ki	=	0.25	nM	9.6	Displacement of [125I]iodosulpiride from human Dopamine receptor D3 expressed in...	14521403
D(2) dopamine receptor	IC50	=	0.25	nM	9.6	Displacement of [3H]Spiperone from human recombinant dopamine D2S receptor expre...	23403082

Literature References

PubMed	DOI	Target Context	# Activities
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	57
28666735	10.1016/j.bmcl.2017.06.051	D(2) dopamine receptor	6
12825922	10.1021/jm030030n	5-hydroxytryptamine receptor 7	5
3336031	10.1021/jm00396a003	Serotonin receptor 2a and 2c (5HT2A and 5HT2C)	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	4
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
37646374	10.1021/acs.jmedchem.3c00734	D(4) dopamine receptor	4
3746815	10.1021/jm00159a017	Rattus norvegicus	4
37646374	10.1021/acs.jmedchem.3c00734	D(2) dopamine receptor	4
23403082	10.1016/j.bmcl.2013.01.025	D(3) dopamine receptor	3
23403082	10.1016/j.bmcl.2013.01.025	D(4) dopamine receptor	3
23403082	10.1016/j.bmcl.2013.01.025	D(2) dopamine receptor	3
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	3
16033273	10.1021/jm0408969	Unchecked	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	3
18262683	10.1016/j.ejmech.2007.12.025	Cavia porcellus	3
37468498	10.1038/s41467-023-40064-9	Histamine H1 receptor	3
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	3

Data from ChEMBL 36 via Core Engine