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Compound Detail

CHEMBL49623

(R,S)-IFENPRODIL
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C[C@@H]([C@H](O)c1ccc(O)cc1)N1CCC(Cc2ccccc2)CC1

Basic Information

ChEMBL ID CHEMBL49623
Name (R,S)-IFENPRODIL
Phase Preclinical
Structure Type MOL
InChI Key UYNVMODNBIQBMV-KKSFZXQISA-N
16
Targets
27
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

325.4
MW (Da)
3.77
ALogP
3
HBA
2
HBD
43.7
PSA (Ų)
0.88
QED
0
Ro5 Violations
5
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 8.34
IC50 10 meas. best 7.0
Kd 2 meas. best 8.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma intracellular receptor 2
CHEMBL4105864
Ki 8.34 7.675 4.6 2
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
Kd 8.12 7.575 7.6 2
Unchecked
CHEMBL612545
Ki 8.0 7.945 10.0 2
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 7.92 7.92 12.0 1
Glutamate [NMDA] receptor
CHEMBL2094124
Ki 7.89 7.89 13.0 1
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
Ki 7.84 7.84 14.4 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
Ki 7.66 7.28 22.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.02 7.02 95.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 7.0 6.8825 100.0 4
Glutamate NMDA receptor; Grin1/Grin2b
CHEMBL2096666
IC50 6.96 6.96 110.0 1
Glutamate NMDA receptor
CHEMBL1907608
IC50 6.96 6.77 110.0 2
Alpha-1A adrenergic receptor
CHEMBL229
Ki 6.85 6.85 140.0 1
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
IC50 6.7 6.7 200.0 1
Glutamate receptor ionotropic, NMDA 2C
CHEMBL401
IC50 6.58 6.58 263.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.38 6.38 421.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.29 6.29 513.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.13 6.13 748.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.8 5.8 1600.0 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
Sigma intracellular receptor 2 Ki = 4.6 nM 8.34 Displacement of [3H](+)-[3H]di-o-tolylguanidine from sigma2 receptor in rat live... 33426889
Glutamate receptor ionotropic, NMDA 2B Kd = 7.6 nM 8.12 Binding affinity to GluN2B (unknown origin) expressed in mouse L(tk-) cell membr... 31129453
Unchecked Ki = 10.0 nM 8.0 Displacement of [3H] ifenprodil from GluN2B/GluN1a (unknown origin) expressed in... 31129453
Adrenergic receptor alpha-1 Ki = 12.0 nM 7.92 Binding affinity towards Alpha-1 adrenergic receptor in rat brain using [3H]praz... 12729659
Unchecked Ki = 13.0 nM 7.89 Inhibition of [3H]25-6981 binding to N-methyl-D-aspartate glutamate receptor 2B ... 12729659
Glutamate [NMDA] receptor Ki = 13.0 nM 7.89 Binding affinity against NMDA receptor by displacement of [3H]Ro-256981 12617901
Glutamate receptor ionotropic, NMDA 2B Ki = 14.4 nM 7.84 Displacement of [3H]-unlike-ifenprodil from recombinant human GluN2B expressed i... 33426889
Sigma non-opioid intracellular receptor 1 Ki = 22.0 nM 7.66 Displacement of [3H](+)-pentazocine from sigma1 receptor in guinea pig brain mem... 33426889
Glutamate receptor ionotropic, NMDA 2B Kd = 94.0 nM 7.03 Binding affinity towards human NR2B receptor 12639561
5-hydroxytryptamine receptor 2B Ki = 95.0 nM 7.02 Binding affinity to 5-HT2B receptor (unknown origin) incubated for 1 hr by radio... 33426889
Sigma intracellular receptor 2 Ki = 98.0 nM 7.01 Displacement of [3H]-di-o-tolylguanidine from sigma2 receptor in rat liver membr... 31129453
Adrenergic receptor alpha-1 IC50 = 100.0 nM 7.0 Tested for the Alpha-1 adrenergic receptor affinity in a standard radioligand bi... -
Adrenergic receptor alpha-1 IC50 = 100.0 nM 7.0 In vitro binding affinity against Alpha-1 adrenergic receptor using [3H]prazosin... 7636876
Glutamate NMDA receptor IC50 = 110.0 nM 6.96 N-methyl-D-aspartate glutamate receptor antagonistic activity in cell culture(CC... 1681106
Glutamate NMDA receptor; Grin1/Grin2b IC50 = 110.0 nM 6.96 In vitro inhibitory concentration against NMDA responses at NR1A/2B receptors ex... 10425109
Sigma non-opioid intracellular receptor 1 Ki = 125.0 nM 6.9 Displacement of [3H]-(+)-pentazocine from sigma1 receptor in guinea pig brain co... 31129453
Adrenergic receptor alpha-1 IC50 = 135.0 nM 6.87 Binding affinity against alpha-1 adrenergic receptor 1681106
Alpha-1A adrenergic receptor Ki = 140.0 nM 6.85 Displacement of [3H]prazosin from alpha-1A adrenergic receptor (unknown origin) 33426889
Glutamate receptor ionotropic, NMDA 2B IC50 = 200.0 nM 6.7 Antagonist activity at human GluN2B expressed in Xenopus laevis oocytes assessed... 33426889
Adrenergic receptor alpha-1 IC50 = 220.0 nM 6.66 Affinity for alpha-1 adrenergic receptor in rat was determined by [3H]- prazosin... 10425109

Literature References

PubMed DOI Target Context # Activities
33426889 10.1021/acs.jmedchem.0c01912 Glutamate receptor ionotropic, NMDA 2B 3
31129453 10.1016/j.ejmech.2019.05.034 Unchecked 2
1681106 10.1021/jm00114a018 Adrenergic receptor alpha-1 2
1681106 10.1021/jm00114a018 Glutamate NMDA receptor 2
- 10.1016/S0960-894X(00)80098-0 Adrenergic receptor alpha-1 1
33426889 10.1021/acs.jmedchem.0c01912 Unchecked 1
12729659 10.1016/s0960-894x(03)00232-4 Mus musculus 1
12729659 10.1016/s0960-894x(03)00232-4 Adrenergic receptor alpha-1 1
12729659 10.1016/s0960-894x(03)00232-4 Unchecked 1
12617901 10.1016/s0960-894x(03)00007-6 Glutamate [NMDA] receptor 1
- 10.1016/S0960-894X(00)80098-0 Unchecked 1
10425109 10.1021/jm990246i Glutamate NMDA receptor; Grin1/Grin2a 1
- 10.1016/S0960-894X(00)80098-0 Glutamate receptor ionotropic, NMDA 2C 1
7636876 10.1021/jm00016a017 Unchecked 1
7636876 10.1021/jm00016a017 Adrenergic receptor alpha-1 1
7636876 10.1021/jm00016a017 Glutamate NMDA receptor 1
10425109 10.1021/jm990246i Mus musculus 1
10425109 10.1021/jm990246i Rattus 1
10425109 10.1021/jm990246i Adrenergic receptor alpha-1 1
10425109 10.1021/jm990246i Glutamate NMDA receptor; Grin1/Grin2c 1

Data from ChEMBL 36 via Core Engine