Compound Detail

CHEMBL416526

BUFOTENINE

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CN(C)CCc1c[nH]c2ccc(O)cc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL416526
Name	BUFOTENINE
Phase	Preclinical
Structure Type	MOL
InChI Key	VTTONGPRPXSUTJ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

204.3

MW (Da)

1.98

ALogP

HBA

HBD

39.3

PSA (Å²)

0.80

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	C12H16N2O
MW	204.27
Aromatic Rings	2
Heavy Atoms	15
NP-Likeness	0.19

Activity Summary

Ki 8 meas. best 8.1

IC50 4 meas. best 5.92

Kd 2 meas. best 8.5

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 1A CHEMBL214	Kd	8.5	8.5	3.2	1
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	8.1	8.1	7.9	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.6	7.095	25.1	2
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Kd	7.41	7.41	38.9	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	7.16	7.16	70.0	1
Rattus norvegicus CHEMBL376	Ki	6.47	5.835	341.0	2
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	6.42	6.42	380.0	1
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	6.04	6.04	910.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	5.92	5.92	1200.0	1
Rattus norvegicus CHEMBL376	IC50	5.88	5.39	1318.3	2
Acetylcholinesterase CHEMBL4078	IC50	4.94	4.94	11400.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 1A	Kd	=	3.162	nM	8.5	Binding affinity to 5HT1A receptor	19754201
5-hydroxytryptamine receptor 7	Ki	=	7.943	nM	8.1	Binding affinity at rat 5-hydroxytryptamine 7 receptor.	14640545
5-hydroxytryptamine receptor 1A	Ki	=	25.12	nM	7.6	Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) r...	8568799
Serotonin 1 (5-HT1) receptor	Kd	=	38.9	nM	7.41	Antagonist activity at 5-HT1 receptor in Sprague-Dawley rat assessed as inhibiti...	533890
5-hydroxytryptamine receptor 2C	Ki	=	70.0	nM	7.16	Evaluated for the binding affinity to porcine choroid plexus at 5-hydroxytryptam...	3543362
5-hydroxytryptamine receptor 1A	Ki	=	259.0	nM	6.59	Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydrox...	3543362
Rattus norvegicus	Ki	=	341.0	nM	6.47	Compound was evaluated for its activity at membrane-bound receptor (M+L+P fracti...	3746815
Serotonin 2 (5-HT2) receptor	Ki	=	380.0	nM	6.42	Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece...	3543362
5-hydroxytryptamine receptor 1B	Ki	=	910.0	nM	6.04	Binding affinity (Ki) to rat cortical membranes at 5-HT1B binding site by using ...	3543362
Sodium-dependent serotonin transporter	IC50	=	1200.0	nM	5.92	Inhibitory concentration against serotonin transporter protein (SERT) expressed ...	15745809
Rattus norvegicus	IC50	=	1318.26	nM	5.88	Compound was evaluated for its activity at membrane-bound receptor (M+L+P fracti...	3746815
Rattus norvegicus	Ki	=	6295.0	nM	5.2	Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solu...	3746815
Acetylcholinesterase	IC50	=	11400.0	nM	4.94	Inhibition of Electric eel AChE assessed as amount of thiocholine released using...	24521095
Rattus norvegicus	IC50	=	12589.25	nM	4.9	Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solu...	3746815

Literature References

PubMed	DOI	Target Context	# Activities
6259355	10.1021/jm00134a016	No relevant target	5
3746815	10.1021/jm00159a017	Rattus norvegicus	4
7658443	10.1021/jm00018a016	5-hydroxytryptamine receptor 1D	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
14640545	10.1021/jm030826m	5-hydroxytryptamine receptor 7	2
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	1
6127411	10.1021/jm00351a015	GABA-A receptor; anion channel	1
8568799	10.1021/jm950410b	5-hydroxytryptamine receptor 1A	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 2C	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1B	1
7658443	10.1021/jm00018a016	5-hydroxytryptamine receptor 2A	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1A	1
15745809	10.1016/j.bmcl.2005.01.059	Sodium-dependent serotonin transporter	1
19754201	10.1021/jm901096y	5-hydroxytryptamine receptor 1A	1
24521095	10.1021/np401003p	Acetylcholinesterase	1
533890	10.1021/jm00197a025	Serotonin 1 (5-HT1) receptor	1
533890	10.1021/jm00197a025	No relevant target	1
6094812	10.1021/jm00378a021	ADMET	1

Data from ChEMBL 36 via Core Engine