Compound Detail

CHEMBL113830

(S,R)-IFENPRODIL

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C[C@H]([C@@H](O)c1ccc(O)cc1)N1CCC(Cc2ccccc2)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL113830
Name	(S,R)-IFENPRODIL
Phase	Preclinical
Structure Type	MOL
InChI Key	UYNVMODNBIQBMV-IIBYNOLFSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

325.4

MW (Da)

3.77

ALogP

HBA

HBD

43.7

PSA (Å²)

0.88

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	C21H27NO2
MW	325.45
Aromatic Rings	2
Heavy Atoms	24
NP-Likeness	0.06

Activity Summary

Ki 15 meas. best 9.0

IC50 7 meas. best 7.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
C-8 sterol isomerase ERG2 CHEMBL3224	Ki	9.0	9.0	1.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	8.7	8.7	2.0	1
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase CHEMBL4931	Ki	8.3	8.3	5.0	1
Glutamate receptor ionotropic, NMDA 2B CHEMBL1904	Ki	8.11	8.055	7.8	2
Sigma intracellular receptor 2 CHEMBL4105864	Ki	7.82	7.415	15.0	2
Alpha-1A adrenergic receptor CHEMBL229	Ki	7.57	7.57	27.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.34	7.34	46.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.18	7.18	66.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL4153	Ki	7.12	7.01	75.0	2
Alpha-1A adrenergic receptor CHEMBL229	IC50	7.0	7.0	100.0	1
Glutamate NMDA receptor; Grin1/Grin2b CHEMBL2096666	IC50	6.96	6.96	110.0	1
Sodium-dependent dopamine transporter CHEMBL338	Ki	6.44	6.44	363.1	1
Glutamate NMDA receptor CHEMBL1907608	IC50	6.33	6.32	470.0	3
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.29	6.29	510.0	1
Glutamate receptor ionotropic, NMDA 2B CHEMBL1904	IC50	6.16	6.16	698.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.64	5.64	2300.0	1
Glutamate NMDA receptor; Grin1/Grin2a CHEMBL2096680	IC50	4.7	4.7	20000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
C-8 sterol isomerase ERG2	Ki	=	1.0	nM	9.0	Affinity for ERG2 of Saccharomyces cerevisiae using [3H]ifenprodil or (+)-[3H]pe...	16033255
Sigma non-opioid intracellular receptor 1	Ki	=	2.0	nM	8.7	Affinity for sigma receptor type 1 of guinea pig using [3H]ifenprodil or (+)-[3H...	16033255
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Ki	=	5.0	nM	8.3	Affinity for human EMP expressed in ERG2 deficient strain of Saccharomyces cerev...	16033255
Glutamate receptor ionotropic, NMDA 2B	Ki	=	7.8	nM	8.11	Displacement of [3H]-unlike-ifenprodil from recombinant human GluN2B expressed i...	33426889
Glutamate receptor ionotropic, NMDA 2B	Ki	=	10.0	nM	8.0	Displacement of [3H]ifenprodil from human GluN2B expressed in mouse L(tk-) cell ...	31255496
Sigma intracellular receptor 2	Ki	=	15.0	nM	7.82	Displacement of [3H](+)-[3H]di-o-tolylguanidine from sigma2 receptor in rat live...	33426889
Alpha-1A adrenergic receptor	Ki	=	27.0	nM	7.57	Displacement of [3H]prazosin from alpha-1A adrenergic receptor (unknown origin)	33426889
5-hydroxytryptamine receptor 1A	Ki	=	46.0	nM	7.34	Displacement of [3H]-8-OH-DPAT from human 5-HT1A receptor expressed in HEK293 ce...	33426889
5-hydroxytryptamine receptor 2B	Ki	=	66.0	nM	7.18	Binding affinity to 5-HT2B receptor (unknown origin) incubated for 1 hr by radio...	33426889
Sigma non-opioid intracellular receptor 1	Ki	=	75.0	nM	7.12	Displacement of [3H](+)-pentazocine from sigma1 receptor in guinea pig brain mem...	33426889
Sigma intracellular receptor 2	Ki	=	98.0	nM	7.01	Displacement of [3H]-Di-o-tolylguanidine from sigma-2 receptor in rat liver memb...	31255496
Alpha-1A adrenergic receptor	IC50	=	100.0	nM	7.0	Inhibition of Alpha-1 adrenergic receptor	10464027
Glutamate NMDA receptor; Grin1/Grin2b	IC50	=	110.0	nM	6.96	Antagonistic activity against N-methyl-D-aspartate glutamate receptor 1/2B.	10464027
Sigma non-opioid intracellular receptor 1	Ki	=	125.0	nM	6.9	Displacement of [3H]-(+)pentazocine from sigma-1 receptor in guinea pig brain me...	31255496
Sodium-dependent dopamine transporter	Ki	=	363.08	nM	6.44	Binding affinity to dopamine transporter (DAT) using [3H]WIN-35428 as a radiolig...	11063611
Glutamate NMDA receptor	IC50	=	470.0	nM	6.33	Inhibition of NMDA receptor in rat cortical cells assessed as NMDA-evoked increa...	17074483
Glutamate NMDA receptor	IC50	=	470.0	nM	6.33	Inhibition of NMDA-evoked intracellular calcium increase in rat cortical cells	16213709
Glutamate NMDA receptor	IC50	=	500.0	nM	6.3	Negative allosteric modulator activity at NMDA receptor in Wistar rat hippocampa...	35923717
5-hydroxytryptamine receptor 2A	Ki	=	510.0	nM	6.29	Displacement of [3H]ketanserin from human 5-HT2A receptor expressed in CHO-K1 ce...	33426889
Glutamate receptor ionotropic, NMDA 2B	IC50	=	698.0	nM	6.16	Antagonist activity at human GluN2B expressed in Xenopus laevis oocytes assessed...	33426889

Literature References

PubMed	DOI	Target Context	# Activities
33426889	10.1021/acs.jmedchem.0c01912	Glutamate receptor ionotropic, NMDA 2B	3
35923717	10.1039/d2md00001f	Glutamate NMDA receptor	2
17074483	10.1016/j.bmcl.2006.10.033	Unchecked	1
33426889	10.1021/acs.jmedchem.0c01912	5-hydroxytryptamine receptor 1A	1
33426889	10.1021/acs.jmedchem.0c01912	Sigma intracellular receptor 2	1
33426889	10.1021/acs.jmedchem.0c01912	Sigma non-opioid intracellular receptor 1	1
33426889	10.1021/acs.jmedchem.0c01912	Alpha-2A adrenergic receptor	1
33426889	10.1021/acs.jmedchem.0c01912	Alpha-1A adrenergic receptor	1
31255496	10.1016/j.bmc.2019.06.035	Sigma intracellular receptor 2	1
31255496	10.1016/j.bmc.2019.06.035	Sigma non-opioid intracellular receptor 1	1
31255496	10.1016/j.bmc.2019.06.035	Glutamate receptor ionotropic, NMDA 2B	1
10464027	10.1021/jm990199u	Glutamate NMDA receptor; Grin1/Grin2a	1
17074483	10.1016/j.bmcl.2006.10.033	Glutamate NMDA receptor	1
16213709	10.1016/j.bmcl.2005.08.110	Glutamate NMDA receptor	1
16033255	10.1021/jm049073+	C-8 sterol isomerase ERG2	1
16033255	10.1021/jm049073+	Sigma non-opioid intracellular receptor 1	1
16033255	10.1021/jm049073+	3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	1
11063611	10.1021/jm990472s	Sodium-dependent dopamine transporter	1
10464027	10.1021/jm990199u	Alpha-1A adrenergic receptor	1
10464027	10.1021/jm990199u	Glutamate NMDA receptor; Grin1/Grin2c	1

Data from ChEMBL 36 via Core Engine