Compound Detail

CHEMBL56

8-OH-DPAT

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CCCN(CCC)C1CCc2cccc(O)c2C1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL56
Name	8-OH-DPAT
Phase	Preclinical
Structure Type	MOL
InChI Key	ASXGJMSKWNBENU-UHFFFAOYSA-N

Targets

223

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

247.4

MW (Da)

3.37

ALogP

HBA

HBD

23.5

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	C16H25NO
MW	247.38
Aromatic Rings	1
Heavy Atoms	18
NP-Likeness	-0.31

Activity Summary

Ki 161 meas. best 9.8

IC50 37 meas. best 9.55

EC50 24 meas. best 8.59

Kd 1 meas. best 8.6

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	9.8	8.7447	0.2	53
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	9.57	8.7806	0.3	49
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	9.55	9.164	0.3	10
Rattus norvegicus CHEMBL376	Ki	9.04	9.04	0.9	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	8.96	8.5208	1.1	12
Serotonin 3 (5-HT3) receptor CHEMBL2094116	Ki	8.92	8.92	1.2	1
5-hydroxytryptamine receptor 1A CHEMBL273	Kd	8.6	8.6	2.5	1
5-hydroxytryptamine receptor 1A CHEMBL214	EC50	8.59	7.8816	2.6	19
D(2) dopamine receptor CHEMBL339	IC50	8.28	6.76	5.2	4
5-hydroxytryptamine receptor 1A CHEMBL273	EC50	7.85	7.85	14.0	1
HeLa CHEMBL399	EC50	7.75	7.75	18.0	1
D(2) dopamine receptor CHEMBL217	Ki	7.08	6.6775	84.0	4
D(2) dopamine receptor CHEMBL339	Ki	7.07	6.1775	86.0	8
Serotonin 1 (5-HT1) receptor CHEMBL2095159	IC50	7.0	7.0	100.0	1
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	6.94	6.865	115.0	2
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	6.82	6.82	150.0	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	6.82	6.285	151.4	4
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	6.8	6.8	160.0	1
D(3) dopamine receptor CHEMBL3138	Ki	6.61	6.5633	248.0	3
D(3) dopamine receptor CHEMBL234	Ki	6.59	5.715	259.0	2
5-hydroxytryptamine receptor 1B CHEMBL1898	EC50	6.58	6.58	260.0	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	6.41	6.372	388.0	5
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	6.25	6.225	559.0	2
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	6.2	5.608	635.0	5
D(2) dopamine receptor CHEMBL3998	IC50	6.1	6.1	800.0	2
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	6.09	6.09	810.0	2
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	6.08	6.08	831.8	1
Alpha-2A adrenergic receptor CHEMBL4744	IC50	6.0	6.0	1000.0	1
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	6.0	5.7333	1000.0	3
Unchecked CHEMBL612545	Ki	5.96	5.49	1100.0	2
Serotonin 2 (5-HT2) receptor CHEMBL2095200	Ki	5.79	5.79	1614.0	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	5.72	5.3867	1882.0	3
Alpha-1A adrenergic receptor CHEMBL319	Ki	5.68	5.68	2082.0	1
D(2) dopamine receptor CHEMBL3998	Ki	5.62	5.62	2380.0	1
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	5.59	4.895	2570.0	2
5-hydroxytryptamine receptor 1B CHEMBL3459	IC50	5.42	5.42	3801.9	1
Sigma non-opioid intracellular receptor 1 CHEMBL3602	Ki	5.28	5.28	5240.0	1
Alpha-1D adrenergic receptor CHEMBL326	Ki	5.27	5.27	5421.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.14	4.985	7250.0	2
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	5.0	5.0	10000.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	4.75	4.75	18000.0	1
Alpha-1A adrenergic receptor CHEMBL4892	IC50	4.52	4.52	30000.0	1
5-hydroxytryptamine receptor 2A CHEMBL3446	IC50	4.31	4.31	49000.0	1
Unchecked CHEMBL612545	IC50	4.31	4.31	49000.0	1
D(1A) dopamine receptor CHEMBL2967	Ki	4.06	4.06	87300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	213.0	pM hr-1 g-1	-
AUC	104.0	pM hr-1 g-1	-
AUC	213.0	pM ml-1	Rattus norvegicus
AUC	104.0	pM ml-1	Rattus norvegicus
Cmax	344.0	nM	-
Cmax	63.0	nM	-
Cmax	344.0	min	-
Cmax	63.0	min	-
F	2.4	%	Rattus norvegicus
F	2.4	%	Rattus norvegicus
T1/2	1.2	hr	Rattus norvegicus
T1/2	1.0	hr	Rattus norvegicus
T1/2	1.2	hr	-
T1/2	1.2	%	Rattus norvegicus
Tmax	0.05	hr	-
Tmax	0.4833	hr	-
Tmax	3.0	hr	-
Tmax	29.0	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 1A	Ki	=	0.16	nM	9.8	Binding affinity to human 5-HT1A receptor extracted from HEK293 cell membrane as...	38552597
5-hydroxytryptamine receptor 1A	Ki	=	0.17	nM	9.77	Displacement of [3H]8-OH-DPAT from human 5HT1A receptor	21726069
5-hydroxytryptamine receptor 1A	Ki	=	0.18	nM	9.74	Displacement of [3H]OH-DPAT from human recombinant 5-HT1A receptor measured afte...	31112891
5-hydroxytryptamine receptor 1A	Ki	=	0.21	nM	9.68	Binding affinity to human 5-HT1A receptor by radioligand displacement assay	23466604
5-hydroxytryptamine receptor 1A	Ki	=	0.27	nM	9.57	The compound was evaluated for binding affinity against 5-hydroxytryptamine 1A r...	-
5-hydroxytryptamine receptor 1A	IC50	=	0.28	nM	9.55	Displacement of [3H]OH-DPAT from human recombinant 5-HT1A receptor measured afte...	31112891
5-hydroxytryptamine receptor 1A	Ki	=	0.31	nM	9.51	Binding affinity to 5HT1A receptor (unknown origin) assessed as inhibition const...	28849908
5-hydroxytryptamine receptor 1A	IC50	=	0.33	nM	9.48	Binding affinity to human 5-HT1A receptor by radioligand displacement assay	23466604
5-hydroxytryptamine receptor 1A	Ki	=	0.4	nM	9.4	Displacement of [3H]-8-OH-DPAT from human 5-HT1A receptor expressed in HEK-293 c...	25557493
5-hydroxytryptamine receptor 1A	Ki	=	0.4	nM	9.4	Tested in vitro for the inhibition of [3H]8-OH-DPAT binding to 5-hydroxytryptami...	-
5-hydroxytryptamine receptor 1A	Ki	=	0.4	nM	9.4	Displacement of [3H]8-OH-DPAT from human recombinant 5-HT1A receptor expressed i...	24805037
5-hydroxytryptamine receptor 1A	Ki	=	0.47	nM	9.33	Displacement of [3H]8-OH-DPAT from rat striata 5-hydroxytryptamine 1A receptor	10743959
5-hydroxytryptamine receptor 1A	Ki	=	0.5	nM	9.3	Binding affinity against rat 5-hydroxytryptamine 1A receptor	9083484
5-hydroxytryptamine receptor 1A	Ki	=	0.5	nM	9.3	Binding affinity against [3H]- -8-OH-DPAT -labeled 5-hydroxytryptamine 1A sites ...	8340922
5-hydroxytryptamine receptor 1A	Ki	=	0.5	nM	9.3	Binding affinity against 5-hydroxytryptamine 1A receptor from CHO-K1 cells, usin...	7783152
5-hydroxytryptamine receptor 1A	Ki	=	0.5	nM	9.3	Displacement of [3H]8-OH-DPAT from 5-hydroxytryptamine 1A receptor of rat hippoc...	9083484
5-hydroxytryptamine receptor 1A	Ki	=	0.5	nM	9.3	In vitro displacement of radioactively labeled ligand [3H]8-OH-DPAT from 5-hydro...	7861420
5-hydroxytryptamine receptor 1A	IC50	=	0.51	nM	9.29	Binding affinity to human 5-HT1A receptor by radioligand displacement assay	23582449
5-hydroxytryptamine receptor 1A	IC50	=	0.53	nM	9.28	Displacement of [3H]8-OHDPAT from human recombinant 5-HT1A receptor expressed in...	26988801
5-hydroxytryptamine receptor 1A	IC50	=	0.53	nM	9.28	Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in...	27876250

Literature References

PubMed	DOI	Target Context	# Activities
8340922	10.1021/jm00067a018	Rattus norvegicus	21
2967374	10.1021/jm00401a005	Rattus norvegicus	20
3339604	10.1021/jm00397a007	Rattus norvegicus	16
8097537	10.1021/jm00060a014	Mus musculus	15
8459396	10.1021/jm00058a003	Mus musculus	15
8230131	10.1021/jm00074a022	Rattus norvegicus	15
32883072	10.1021/acs.jmedchem.0c00814	5-hydroxytryptamine receptor 1A	15
8097538	10.1021/jm00060a015	Mus musculus	15
8340910	10.1021/jm00067a002	Rattus norvegicus	14
19665823	10.1016/j.ejmech.2009.07.007	Mus musculus	12
30721053	10.1021/acs.jmedchem.9b00062	5-hydroxytryptamine receptor 1A	12
7783152	10.1021/jm00012a021	Rattus norvegicus	10
1433207	10.1021/jm00100a002	Rattus norvegicus	8
3339604	10.1021/jm00397a007	Unchecked	8
8340910	10.1021/jm00067a002	ADMET	8
12213056	10.1021/jm0111200	5-hydroxytryptamine receptor 1A	8
7932553	10.1021/jm00046a010	Rattus norvegicus	7
-	10.1016/S0960-894X(97)10068-3	Rattus norvegicus	6
8097537	10.1021/jm00060a014	Rattus norvegicus	6
11728188	10.1021/jm010866v	5-hydroxytryptamine receptor 1A	6

Data from ChEMBL 36 via Core Engine