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Compound Detail

CHEMBL319706

(S)-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 CHEMBL319706
Name (S)-IFENPRODIL
Phase Preclinical
Structure Type MOL
InChI Key UYNVMODNBIQBMV-HRAATJIYSA-N
12
Targets
29
Activities
2
Assay Types
2
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 16 meas. best 8.07
IC50 13 meas. best 7.88

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma intracellular receptor 2
CHEMBL4105864
 Ki 8.07 8.07 8.6 1
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
 Ki 8.0 7.9567 10.0 3
Glutamate NMDA receptor; GRIN1/GRIN2B
CHEMBL1907603
 Ki 8.0 8.0 10.0 2
Glutamate NMDA receptor; GRIN1/GRIN2B
CHEMBL1907603
 IC50 7.88 7.88 13.3 1
Glutamate NMDA receptor
CHEMBL1907608
 IC50 7.88 7.43 13.3 4
Unchecked
CHEMBL612545
 IC50 7.88 7.88 13.3 1
Glutamate receptor ionotropic, NMDA 2C
CHEMBL401
 IC50 7.26 7.26 55.0 1
Unchecked
CHEMBL612545
 Ki 7.01 7.01 98.0 3
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.9 6.9 125.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 6.9 6.7867 125.0 3
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.43 6.43 369.0 1
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
 IC50 6.28 6.28 525.0 1
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 6.28 6.28 530.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
 IC50 6.2 6.01 629.0 5
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 5.21 5.21 6100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 108.6 mL.min-1.g-1 Homo sapiens
T1/2 0.2133 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma intracellular receptor 2 Ki = 8.6 nM 8.07 Displacement of [3H](+)-[3H]di-o-tolylguanidine from sigma2 receptor in rat live... 33426889
Glutamate NMDA receptor; GRIN1/GRIN2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from human NR1-1a/NR2B receptor expressed in Mous... 28797770
Glutamate receptor ionotropic, NMDA 2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from recombinant human GluN2B expressed in mouse ... 27061977
Glutamate NMDA receptor; GRIN1/GRIN2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from recombinant human GluN1a/GluN2B expressed in... 26750254
Glutamate receptor ionotropic, NMDA 2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from Glun2B receptor (unknown origin) expressed i... 26531150
Glutamate NMDA receptor; GRIN1/GRIN2B IC50 = 13.3 nM 7.88 Displacement of [3H]ifenprodil from human NR1a/NR2B receptor expressed in mouse ... 26531150
Glutamate NMDA receptor IC50 = 13.3 nM 7.88 N-methyl-D-aspartate glutamate receptor antagonistic activity in cell culture(CC... 1681106
Unchecked IC50 = 13.3 nM 7.88 Binding affinity to Xenopus laevis GluN2B expressed in HEK293S GnTI- cells by sc... 27061977
Glutamate receptor ionotropic, NMDA 2B Ki = 13.5 nM 7.87 Displacement of [3H]-unlike-ifenprodil from recombinant human GluN2B expressed i... 33426889
Glutamate NMDA receptor IC50 = 48.0 nM 7.32 N-methyl-D-aspartate glutamate receptor antagonistic activity in cell culture(CC... 1681106
Glutamate NMDA receptor IC50 = 55.0 nM 7.26 N-methyl-D-aspartate glutamate receptor antagonistic activity in cell culture(CC... 1681106
Glutamate NMDA receptor IC50 = 55.0 nM 7.26 In vitro inhibition of glutamate induced neuronal death in primary cultures of r... 7636876
Glutamate receptor ionotropic, NMDA 2C IC50 = 55.0 nM 7.26 Tested for the NMDA antagonist activity using a functional assay, by protection ... -
Unchecked Ki = 98.0 nM 7.01 Displacement of [3H]DTG from sigma2 receptor in rat liver membranes by scintilla... 26531150
Unchecked Ki = 98.0 nM 7.01 Binding affinity to sigma-2 receptor (unknown origin) by radioligand displacemen... 26750254
Unchecked Ki = 98.3 nM 7.01 Displacement of [3H]DTG from sigma2 receptor in rat liver homogenate incubated f... 27061977
Sigma non-opioid intracellular receptor 1 Ki = 125.0 nM 6.9 Binding affinity to sigma-1 receptor (unknown origin) by radioligand displacemen... 26750254
Sigma non-opioid intracellular receptor 1 Ki = 125.0 nM 6.9 Displacement of [3H]-(+)-Pentazocine from sigma1 receptor in guinea pig brain ho... 27061977
Sigma non-opioid intracellular receptor 1 Ki = 125.0 nM 6.9 Displacement of [3H]-(+)-Pentazocine from sigma1 receptor in guniea pig brain co... 26531150
Sigma non-opioid intracellular receptor 1 Ki = 278.0 nM 6.56 Displacement of [3H](+)-pentazocine from sigma1 receptor in guinea pig brain mem... 33426889

Literature References

PubMed DOI Target Context # Activities
29604542 10.1016/j.ejmech.2018.03.052 SH-SY5Y 4
29604542 10.1016/j.ejmech.2018.03.052 ADMET 3
1681106 10.1021/jm00114a018 Glutamate NMDA receptor 3
1681106 10.1021/jm00114a018 Adrenergic receptor alpha-1 3
1681106 10.1021/jm00114a018 ADMET 3
31494474 10.1016/j.ejmech.2019.111654 SH-SY5Y 3
33426889 10.1021/acs.jmedchem.0c01912 Glutamate receptor ionotropic, NMDA 2B 3
28797770 10.1016/j.bmc.2017.07.059 Unchecked 2
27061977 10.1016/j.ejmech.2016.03.065 Unchecked 2
26531150 10.1016/j.bmcl.2015.10.076 Glutamate receptor ionotropic, NMDA 2B 1
27061977 10.1016/j.ejmech.2016.03.065 Glutamate receptor ionotropic, NMDA 2B 1
33426889 10.1021/acs.jmedchem.0c01912 5-hydroxytryptamine receptor 7 1
26750254 10.1016/j.bmcl.2015.12.067 Sigma non-opioid intracellular receptor 1 1
26531150 10.1016/j.bmcl.2015.10.076 Glutamate NMDA receptor; GRIN1/GRIN2B 1
26531150 10.1016/j.bmcl.2015.10.076 Unchecked 1
26531150 10.1016/j.bmcl.2015.10.076 Sigma non-opioid intracellular receptor 1 1
- 10.1016/S0960-894X(00)80098-0 Unchecked 1
- 10.1016/S0960-894X(00)80098-0 Adrenergic receptor alpha-1 1
- 10.1016/S0960-894X(00)80098-0 Glutamate receptor ionotropic, NMDA 2C 1
7636876 10.1021/jm00016a017 Unchecked 1

Data from ChEMBL 36 via Core Engine