Compound Detail

CHEMBL305195

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C[C@@H](CN1CCC(Cc2ccccc2)CC1)[C@@H](O)c1ccc(O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL305195
Phase	Preclinical
Structure Type	MOL
InChI Key	WVZSEUPGUDIELE-HTAPYJJXSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

339.5

MW (Da)

4.02

ALogP

HBA

HBD

43.7

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C22H29NO2
MW	339.48
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	-0.02

Activity Summary

IC50 20 meas. best 8.22

Ki 6 meas. best 8.25

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Glutamate [NMDA] receptor CHEMBL2094124	Ki	8.25	8.235	5.6	2
Glutamate [NMDA] receptor CHEMBL2094124	IC50	8.22	8.22	6.0	2
Glutamate receptor ionotropic, NMDA 2B CHEMBL311	IC50	8.22	7.7467	6.0	3
Glutamate receptor ionotropic, NMDA 2B CHEMBL1904	IC50	8.05	8.05	9.0	3
Glutamate NMDA receptor; Grin1/Grin2b CHEMBL2096666	IC50	8.05	7.98	9.0	4
Glutamate NMDA receptor; GRIN1/GRIN2B CHEMBL1907603	Ki	8.0	8.0	10.0	1
Unchecked CHEMBL612545	IC50	7.89	7.82	13.0	2
Glutamate NMDA receptor; GRIN1/GRIN2B CHEMBL1907603	IC50	7.24	7.24	57.0	2
Glutamate NMDA receptor CHEMBL1907608	IC50	6.8	6.8	159.0	1
Unchecked CHEMBL612545	Ki	6.77	6.77	170.0	1
Glutamate receptor ionotropic, NMDA 2B CHEMBL1904	Ki	6.76	6.76	173.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	Ki	6.75	6.75	180.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.4	6.4	400.0	1
Glutamate receptor ionotropic, NMDA 2A CHEMBL1972	IC50	4.28	4.28	52000.0	1
Glutamate NMDA receptor; Grin1/Grin2a CHEMBL2096680	IC50	4.28	4.28	52000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Glutamate [NMDA] receptor	Ki	=	5.6	nM	8.25	Displacement of [3H]25-6981 from N-methyl-D-aspartate glutamate receptor	11514163
Glutamate [NMDA] receptor	IC50	=	6.0	nM	8.22	Inhibition of [3H]-Ro-25-6981 binding to NMDA receptor	15225705
Glutamate [NMDA] receptor	Ki	=	6.0	nM	8.22	Binding affinity against NMDA receptor by displacement of [3H]Ro-256981	12617901
Glutamate [NMDA] receptor	IC50	=	6.0	nM	8.22	Inhibition of [3H]Ro-256981 binding to N-methyl-D-aspartate glutamate receptor	14552795
Glutamate receptor ionotropic, NMDA 2B	IC50	=	6.0	nM	8.22	Displacement of [3H]Ro 25,6981 from NR2B NMDA receptor in rat forebrain	17290978
Glutamate receptor ionotropic, NMDA 2B	IC50	=	6.0	nM	8.22	Displacement of [3H]Ro25-6981 from NR2B NMDA receptor in rat forebrain membrane	16782335
Glutamate NMDA receptor; Grin1/Grin2b	IC50	=	9.0	nM	8.05	Antagonist activity against rat 1A/2B subtype of N-methyl-D-aspartate (NMDA) rec...	10386947
Glutamate NMDA receptor; Grin1/Grin2b	IC50	=	9.0	nM	8.05	Antagonistic activity against N-methyl-D-aspartate glutamate receptor 1/2B.	10464027
Glutamate NMDA receptor; Grin1/Grin2b	IC50	=	9.0	nM	8.05	Inhibition of rat NMDA receptor NR1C/NR2B subunit expressed in Xenopus laevis oo...	23140383
Glutamate receptor ionotropic, NMDA 2B	IC50	=	9.0	nM	8.05	Negative allosteric modulation of GluN2B receptor (unknown origin) expressed in ...	29446949
Glutamate receptor ionotropic, NMDA 2B	IC50	=	9.0	nM	8.05	Inhibition of GluN2B (unknown origin)	30881618
Glutamate receptor ionotropic, NMDA 2B	IC50	=	9.0	nM	8.05	Antagonist activity at NMDA receptor NR2B subunit (unknown origin)	36870623
Glutamate NMDA receptor; GRIN1/GRIN2B	Ki	=	10.0	nM	8.0	Displacement of [3H]ifenprodil binding to recombinant human NR1a/NR2B receptors ...	12639560
Unchecked	IC50	=	13.0	nM	7.89	Cytoprotection against glutamate/glycine-induced cytotoxicity against mouse LTK ...	31648876
Glutamate NMDA receptor; Grin1/Grin2b	IC50	=	17.0	nM	7.77	Inhibition of rat NMDA receptor NR1F/NR2B subunit expressed in Xenopus laevis oo...	23140383
Unchecked	IC50	=	18.0	nM	7.75	Antagonist activity at GluN2B/GluN1a receptor (unknown origin) expressed in mous...	29289890
Glutamate NMDA receptor; GRIN1/GRIN2B	IC50	=	57.0	nM	7.24	Inhibition of N-methyl-D-aspartate glutamate receptor-evoked increase of intrace...	14552795
Glutamate NMDA receptor; GRIN1/GRIN2B	IC50	=	57.0	nM	7.24	Inhibition of NMDA-evoked increased intracellular [Ca2+] in cells expressing NR1...	15225705
Glutamate receptor ionotropic, NMDA 2B	IC50	=	159.0	nM	6.8	Antagonist activity at NR2B NMDA receptor in Wistar rat neocortical cells assess...	17290978
Glutamate NMDA receptor	IC50	=	159.0	nM	6.8	Inhibition of NMDA-evoked increase in intracellular calcium ion in rat cortical ...	16782335

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5303304	Fibroblast	7
-	10.6019/CHEMBL5303304	U2OS	7
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
-	10.6019/CHEMBL5303304	HEK-293T	3
11514163	10.1016/s0960-894x(01)00392-4	Adrenergic receptor alpha-1	2
31648876	10.1016/j.bmc.2019.115146	Unchecked	2
23140383	10.1021/jm301508d	Glutamate NMDA receptor; Grin1/Grin2b	2
20692832	10.1016/j.bmcl.2010.07.043	Glutamate NMDA receptor; GRIN1/GRIN2B	2
19157884	10.1016/j.bmc.2008.12.058	Mus musculus	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
17290978	10.1021/jm060420k	Glutamate receptor ionotropic, NMDA 2B	2
15225705	10.1016/j.bmcl.2004.05.053	Mus musculus	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
15225705	10.1016/j.bmcl.2004.05.053	Glutamate NMDA receptor; GRIN1/GRIN2B	1
16782335	10.1016/j.bmcl.2006.06.002	Glutamate receptor ionotropic, NMDA 2B	1
15225705	10.1016/j.bmcl.2004.05.053	Glutamate [NMDA] receptor	1
14552795	10.1016/s0960-894x(03)00708-x	Glutamate [NMDA] receptor	1
12617901	10.1016/s0960-894x(03)00007-6	Glutamate [NMDA] receptor	1
10464027	10.1021/jm990199u	Glutamate NMDA receptor; Grin1/Grin2b	1
-	10.6019/CHEMBL5665443	Uracil-DNA glycosylase	1

Data from ChEMBL 36 via Core Engine