Compound Detail

CHEMBL12314

MESULERGINE

🧪 Phase II

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🧪 Phase II

CN1C[C@@H](NS(=O)(=O)N(C)C)C[C@@H]2c3cccc4c3c(cn4C)C[C@H]21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL12314
Name	MESULERGINE
Phase	Phase II
Structure Type	MOL
InChI Key	JLVHTNZNKOSCNB-YSVLISHTSA-N

Known Names

Mesulergina Mesulergine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

362.5

MW (Da)

1.29

ALogP

HBA

HBD

57.6

PSA (Å²)

0.90

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-erg-

Extended Properties

Molecular Formula	C18H26N4O2S
MW	362.50
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	0.09

Activity Summary

Ki 28 meas. best 9.43

IC50 5 meas. best 8.72

Kd 1 meas. best 6.8

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2C CHEMBL324	Ki	9.43	8.8282	0.4	11
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	9.04	8.808	0.9	5
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	8.72	8.72	1.9	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	8.7	8.625	2.0	2
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	8.7	8.55	2.0	2
Serotonin 3 (5-HT3) receptor CHEMBL2094116	IC50	8.67	8.67	2.1	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	8.28	8.28	5.2	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	8.1	8.1	7.9	1
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	8.1	8.1	7.9	1
Unchecked CHEMBL612545	Ki	8.08	8.08	8.3	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.7	7.7	19.9	1
5-hydroxytryptamine receptor 7 CHEMBL3155	IC50	6.92	6.73	120.0	2
5-hydroxytryptamine receptor 1A CHEMBL214	Kd	6.8	6.8	158.5	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	6.52	6.52	300.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.11	6.11	776.0	2
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	4.89	4.89	13000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2C	Ki	=	0.37	nM	9.43	Displacement of [3H]mesulergine (0.5 nM) from rat 5-hydroxytryptamine 2C recepto...	12519065
5-hydroxytryptamine receptor 2C	Ki	=	0.73	nM	9.14	Ability to displace [3H]mesulergine bound to 5-hydroxytryptamine 2C receptor in ...	9513601
5-hydroxytryptamine receptor 2C	Ki	=	0.73	nM	9.14	Binding affinity against 5-hydroxytryptamine 2C receptor of rat cortex	10229626
5-hydroxytryptamine receptor 2C	Ki	=	0.92	nM	9.04	Ability to displace [3H]mesulergine (0.5 nM) from CHO cells of human 5-hydroxytr...	12519065
5-hydroxytryptamine receptor 2C	Ki	=	1.5	nM	8.82	Evaluated for the binding affinity to porcine choroid plexus at 5-hydroxytryptam...	3543362
5-hydroxytryptamine receptor 2C	Ki	=	1.585	nM	8.8	The compound was tested for the binding affinity against 5-hydroxytryptamine 2C ...	10543880
5-hydroxytryptamine receptor 2C	Ki	=	1.82	nM	8.74	Displacement of [3H]5-HT from human recombinant 5-HT2C receptor expressed in HEK...	24878269
5-hydroxytryptamine receptor 2C	Ki	=	1.82	nM	8.74	Displacement of [3H]5-HT from human recombinant 5-HT2C receptor expressed in HEK...	24878269
5-hydroxytryptamine receptor 2C	Ki	=	1.9	nM	8.72	Displacement of [3H]mesulergine from 5HT2C receptor in Sprague-Dawley rat brain ...	27061981
5-hydroxytryptamine receptor 2C	Ki	=	1.9	nM	8.72	Displacement of [3H]mesulergine from 5HT2C receptor in Sprague-Dawley rat brain ...	26820556
5-hydroxytryptamine receptor 2C	Ki	=	1.9	nM	8.72	Displacement of [3H]mesulergine from Sprague-Dawley rat brain cortex serotonin 5...	22133459
5-hydroxytryptamine receptor 2C	Ki	=	1.9	nM	8.72	Binding affinity to 5HT2C receptor in Sprague-Dawley rat frontal cortical homoge...	21440338
5-hydroxytryptamine receptor 2C	Ki	=	1.9	nM	8.72	Displacement of [3H]mesulergine from 5HT2C in Sprague-Dawley rat brain cortex by...	19954866
5-hydroxytryptamine receptor 2C	Ki	=	1.9	nM	8.72	Displacement of [3H]mesulergine from serotonin 5-HT2C receptor in Sprague-Dawley...	28943244
5-hydroxytryptamine receptor 2C	IC50	=	1.9	nM	8.72	Percent inhibition against 5-hydroxytryptamine 2C receptor at 1 uM	16250647
Serotonin 2 (5-HT2) receptor	Ki	=	2.0	nM	8.7	Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece...	3543362
5-hydroxytryptamine receptor 2B	Ki	=	1.995	nM	8.7	Displacement of [3H]-5-5HT from human cloned 5-hydroxytryptamine 2B receptor exp...	-
5-hydroxytryptamine receptor 2C	Ki	=	1.995	nM	8.7	Displacement of [3H]mesulergine from human cloned 5-hydroxytryptamine 2C recepto...	-
Serotonin 3 (5-HT3) receptor	IC50	=	2.13	nM	8.67	Inhibition of radiolabeled [3H]-Zacopride ligand binding to 5-hydroxytryptamine ...	9357534
5-hydroxytryptamine receptor 2B	Ki	=	2.8	nM	8.55	Antagonist activity at human recombinant 5-HT2B receptor in CHOK1 cells measured...	31112891

Literature References

PubMed	DOI	Target Context	# Activities
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	3
24878269	10.1021/jm5003759	5-hydroxytryptamine receptor 2C	2
24878269	10.1021/jm5003759	5-hydroxytryptamine receptor 6	2
25073094	10.1021/jm500880c	5-hydroxytryptamine receptor 7	2
12519065	10.1021/jm020938y	5-hydroxytryptamine receptor 2C	2
31112891	10.1016/j.ejmech.2019.04.064	5-hydroxytryptamine receptor 2B	2
-	10.1016/S0960-894X(96)00503-3	5-hydroxytryptamine receptor 2A	1
19326916	10.1021/jm8014553	5-hydroxytryptamine receptor 7	1
9214741	10.1021/np960644d	Unchecked	1
9357534	10.1021/jm970376w	Serotonin 3 (5-HT3) receptor	1
10843226	10.1016/s0960-894x(00)00166-9	5-hydroxytryptamine receptor 7	1
-	10.1016/S0960-894X(96)00503-3	5-hydroxytryptamine receptor 2C	1
-	10.1016/S0960-894X(96)00503-3	5-hydroxytryptamine receptor 2B	1
10543880	10.1021/jm990151g	5-hydroxytryptamine receptor 2C	1
9513601	10.1021/jm970645i	5-hydroxytryptamine receptor 2C	1
7629808	10.1021/jm00014a021	5-hydroxytryptamine receptor 2C	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 2C	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1B	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1A	1
3543362	10.1021/jm00384a001	Serotonin 1 (5-HT1) receptor	1

Data from ChEMBL 36 via Core Engine