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Compound Detail

CHEMBL537424

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CCCCN1C(=O)C(CC(C)C)NC(=O)C12CCN(Cc1ccc(Oc3ccccc3)cc1)CC2.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL537424
Phase Preclinical
Structure Type MOL
InChI Key UXAMBBJHHKLTIB-UHFFFAOYSA-N
Parent Compound CHEMBL1188807
Active Moiety CHEMBL1188807
5
Targets
13
Activities
1
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

477.6
MW (Da)
4.99
ALogP
4
HBA
1
HBD
61.9
PSA (Ų)
0.55
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H40ClN3O3
MW 514.11
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness -0.30

Activity Summary

IC50 13 meas. best 8.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-C chemokine receptor type 5
CHEMBL274
 IC50 8.08 7.0338 8.3 8
Human immunodeficiency virus 1
CHEMBL378
 IC50 6.8 6.8 160.0 2
Cytochrome P450 2D6
CHEMBL289
 IC50 5.34 5.34 4600.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.23 5.23 5900.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.71 4.71 19700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 290.0 ng.hr.mL-1 Rattus norvegicus
AUC 372.0 ng Rattus norvegicus
AUC 372.0 ng.hr.mL-1 Rattus norvegicus
AUC 96.7 ng.hr.mL-1 Rattus norvegicus
CL 137.0 mL.min-1.kg-1 Rattus norvegicus
CL 137.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 209.36 nM Rattus norvegicus
Cmax 69.72 nM Rattus norvegicus
F 1.3 % Rattus norvegicus
F 1.3 % Rattus norvegicus
F 1.3 % Rattus norvegicus
T1/2 0.2 hr Rattus norvegicus
T1/2 1.262 hr Rattus norvegicus
T1/2 0.2167 hr Rattus norvegicus
T1/2 1.262 hr Rattus norvegicus
T1/2 0.2167 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-C chemokine receptor type 5 IC50 = 8.3 nM 8.08 Displacement of [125I]MIP1-alpha from human CCR5 expressed in CHO cells 17118654
C-C chemokine receptor type 5 IC50 = 83.0 nM 7.08 Inhibition of radio-isotope labeled MIP1-alpha binding to human recombinant CCR5 16821774
C-C chemokine receptor type 5 IC50 = 94.0 nM 7.03 Antagonist activity at human CCR5 expressed in CHO cells assessed as inhibition ... 17118654
C-C chemokine receptor type 5 IC50 = 94.0 nM 7.03 Antagonist activity at human CCR5 receptor overexpressed in CHO cells assessed a... 20005712
C-C chemokine receptor type 5 IC50 = 94.0 nM 7.03 Antagonist activity at human CCR5 receptor expressed in CHO cells assessed as in... 20542438
C-C chemokine receptor type 5 IC50 = 94.0 nM 7.03 Antagonist activity at human CCR5 expressed in CHO cells assessed as inhibition ... 21256008
C-C chemokine receptor type 5 IC50 = 120.0 nM 6.92 Antagonist activity against human recombinant CCR5 expressed in CHO cells assess... 16821774
Human immunodeficiency virus 1 IC50 = 160.0 nM 6.8 Antiviral activity against HIV1 Ba-L(R5) infected in human PBMC by p24 antigen c... 20005712
Human immunodeficiency virus 1 IC50 = 160.0 nM 6.8 Antiviral activity against HIV1 BAL by p24 assay 20542438
C-C chemokine receptor type 5 IC50 = 851.14 nM 6.07 Antagonist activity at human CCR5 expressed in HOS cells assessed as inhibition ... 21256008
Cytochrome P450 2D6 IC50 = 4600.0 nM 5.34 Inhibition of CYP2D6 21256008
Cytochrome P450 2C9 IC50 = 5900.0 nM 5.23 Inhibition of CYP2C9 21256008
Cytochrome P450 3A4 IC50 = 19700.0 nM 4.71 Inhibition of CYP3A4 21256008

Literature References

PubMed DOI Target Context # Activities
21256008 10.1016/j.bmcl.2010.12.109 Rattus norvegicus 8
20542438 10.1016/j.bmc.2010.05.057 Rattus norvegicus 8
16821774 10.1021/jm060051s C-X-C chemokine receptor type 4 2
21256008 10.1016/j.bmcl.2010.12.109 C-C chemokine receptor type 5 2
20542438 10.1016/j.bmc.2010.05.057 Caco-2 2
17118654 10.1016/j.bmcl.2006.10.084 C-C chemokine receptor type 5 2
16821774 10.1021/jm060051s C-C chemokine receptor type 5 2
16821774 10.1021/jm060051s C-C chemokine receptor type 2 2
17118654 10.1016/j.bmcl.2006.10.084 Rattus norvegicus 1
17118654 10.1016/j.bmcl.2006.10.084 Human immunodeficiency virus 1
20005712 10.1016/j.bmcl.2009.11.018 C-C chemokine receptor type 5 1
20005712 10.1016/j.bmcl.2009.11.018 Human immunodeficiency virus 1 1
20542438 10.1016/j.bmc.2010.05.057 C-C chemokine receptor type 5 1
20542438 10.1016/j.bmc.2010.05.057 Liver microsomes 1
20542438 10.1016/j.bmc.2010.05.057 No relevant target 1
20542438 10.1016/j.bmc.2010.05.057 Human immunodeficiency virus 1 1
21256008 10.1016/j.bmcl.2010.12.109 Cytochrome P450 2C9 1
21256008 10.1016/j.bmcl.2010.12.109 Cytochrome P450 2D6 1
21256008 10.1016/j.bmcl.2010.12.109 Cytochrome P450 3A4 1
16821774 10.1021/jm060051s Human immunodeficiency virus 1 1

Data from ChEMBL 36 via Core Engine