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Compound Detail

CHEMBL536743

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CCCCN1C(=O)C(CC2CCCCC2)NC(=O)C12CCN(Cc1ccc(Oc3ccccc3)cc1)CC2.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL536743
Phase Preclinical
Structure Type MOL
InChI Key PIMBSDCVZVPYEY-UHFFFAOYSA-N
Parent Compound CHEMBL1188557
Active Moiety CHEMBL1188557
6
Targets
13
Activities
1
Assay Types
22
PK Parameters
20
Publications
0
Known Names

Molecular Properties

517.7
MW (Da)
5.91
ALogP
4
HBA
1
HBD
61.9
PSA (Ų)
0.45
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C32H44ClN3O3
MW 554.18
Aromatic Rings 2
Heavy Atoms 38
NP-Likeness -0.36

Activity Summary

IC50 13 meas. best 8.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-C chemokine receptor type 5
CHEMBL274
 IC50 8.21 7.6271 6.1 7
Human immunodeficiency virus
CHEMBL613758
 IC50 7.51 7.51 31.0 1
Human immunodeficiency virus 1
CHEMBL378
 IC50 6.47 6.47 337.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.26 5.26 5500.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.11 5.11 7800.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.03 5.03 9300.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 74.4 ng.hr.mL-1 Rattus norvegicus
AUC 400.0 ng.hr.mL-1 Rattus norvegicus
AUC 74.4 ng.hr.mL-1 Rattus norvegicus
AUC 400.0 ng Rattus norvegicus
AUC 400.0 ng.hr.mL-1 Rattus norvegicus
AUC 24.8 ng.hr.mL-1 Rattus norvegicus
CL 113.0 mL.min-1.kg-1 Rattus norvegicus
CL 113.0 mL.min-1.kg-1 Rattus norvegicus
CL 113.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 32.26 nM Rattus norvegicus
Cmax 32.26 nM Rattus norvegicus
Cmax 10.82 nM Rattus norvegicus
F 1.9 % Rattus norvegicus
F 1.9 % Rattus norvegicus
F 1.9 % Rattus norvegicus
T1/2 1.717 hr Rattus norvegicus
T1/2 0.3317 hr Rattus norvegicus
T1/2 0.4 hr Rattus norvegicus
T1/2 1.717 hr Rattus norvegicus
T1/2 0.3317 hr Rattus norvegicus
T1/2 1.717 hr Rattus norvegicus
T1/2 0.3317 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 = 6.1 nM 8.21 Inhibition of radio-isotope labeled MIP1-alpha binding to human recombinant CCR5 16821774
C-C chemokine receptor type 5 IC50 = 6.1 nM 8.21 Displacement of [125I]MIP1-alpha from human CCR5 expressed in CHO cells 17118654
C-C chemokine receptor type 5 IC50 = 28.0 nM 7.55 Antagonist activity at human CCR5 expressed in CHO cells assessed as inhibition ... 17118654
C-C chemokine receptor type 5 IC50 = 28.0 nM 7.55 Antagonist activity at human CCR5 receptor overexpressed in CHO cells assessed a... 20005712
C-C chemokine receptor type 5 IC50 = 28.0 nM 7.55 Antagonist activity at human CCR5 receptor expressed in CHO cells assessed as in... 20542438
C-C chemokine receptor type 5 IC50 = 28.0 nM 7.55 Antagonist activity at human CCR5 expressed in CHO cells assessed as inhibition ... 21256008
Human immunodeficiency virus IC50 = 31.0 nM 7.51 Antiviral activity against HIV 17118654
C-C chemokine receptor type 5 IC50 = 170.0 nM 6.77 Antagonist activity against human recombinant CCR5 expressed in CHO cells assess... 16821774
Human immunodeficiency virus 1 IC50 = 337.0 nM 6.47 Anti-infective activity against HIV1 BAL in MAGI CCR5+ cells 17118654
Cytochrome P450 2C9 IC50 = 5500.0 nM 5.26 Inhibition of CYP2C9 21256008
Cytochrome P450 2D6 IC50 = 7800.0 nM 5.11 Inhibition of CYP2D6 21256008
Cytochrome P450 3A4 IC50 = 9300.0 nM 5.03 Inhibition of CYP3A4 17118654
Cytochrome P450 3A4 IC50 = 9300.0 nM 5.03 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
20005712 10.1016/j.bmcl.2009.11.018 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
20542438 10.1016/j.bmc.2010.05.057 Liver microsomes 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 Cytochrome P450 3A4 1
17118654 10.1016/j.bmcl.2006.10.084 No relevant target 1
20005712 10.1016/j.bmcl.2009.11.018 C-C chemokine receptor type 5 1
20005712 10.1016/j.bmcl.2009.11.018 Liver microsomes 1
17118654 10.1016/j.bmcl.2006.10.084 Human immunodeficiency virus 1 1
20005712 10.1016/j.bmcl.2009.11.018 No relevant target 1
20005712 10.1016/j.bmcl.2009.11.018 Caco-2 1
20542438 10.1016/j.bmc.2010.05.057 C-C chemokine receptor type 5 1
17118654 10.1016/j.bmcl.2006.10.084 Human immunodeficiency virus 1
21256008 10.1016/j.bmcl.2010.12.109 No relevant target 1

Data from ChEMBL 36 via Core Engine