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Compound Detail

CHEMBL536754

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CCCCN1C(=O)[C@@H]([C@H](O)C2CCCCC2)NC(=O)C12CCN(Cc1ccc(Oc3ccccc3)cc1)CC2.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL536754
Phase Preclinical
Structure Type MOL
InChI Key AOOTYIRLUTVCBQ-PQQSRXGVSA-N
Parent Compound CHEMBL1188566
Active Moiety CHEMBL1188566
5
Targets
10
Activities
1
Assay Types
1
PK Parameters
12
Publications
0
Known Names

Molecular Properties

533.7
MW (Da)
4.88
ALogP
5
HBA
2
HBD
82.1
PSA (Ų)
0.48
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C32H44ClN3O4
MW 570.17
Aromatic Rings 2
Heavy Atoms 39
NP-Likeness -0.23

Activity Summary

IC50 10 meas. best 9.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus
CHEMBL613758
 IC50 9.22 9.22 0.6 1
C-C chemokine receptor type 5
CHEMBL274
 IC50 8.96 7.348 1.1 5
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.22 8.22 6.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.43 5.43 3700.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.01 5.01 9800.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 1.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus IC50 = 0.6 nM 9.22 Antiviral activity against HIV 17118654
C-C chemokine receptor type 5 IC50 = 1.1 nM 8.96 Displacement of [125I]MIP1-alpha from human CCR5 expressed in CHO cells 17118654
Human immunodeficiency virus 1 IC50 = 6.0 nM 8.22 Anti-infective activity against HIV1 BAL in MAGI CCR5+ cells 17118654
C-C chemokine receptor type 5 IC50 = 7.762 nM 8.11 Antagonist activity at human CCR5 expressed in HOS cells assessed as inhibition ... 21256008
C-C chemokine receptor type 5 IC50 = 53.0 nM 7.28 Antagonist activity at human CCR5 expressed in CHO cells assessed as inhibition ... 17118654
C-C chemokine receptor type 5 IC50 = 53.0 nM 7.28 Antagonist activity at human CCR5 expressed in CHO cells assessed as inhibition ... 21256008
Cytochrome P450 2C9 IC50 = 3700.0 nM 5.43 Inhibition of CYP2C9 21256008
C-C chemokine receptor type 5 IC50 = 7800.0 nM 5.11 Antagonist activity against human CCR5 receptor assessed as inhibition of HIV1 g... 21658961
Cytochrome P450 2D6 IC50 = 9800.0 nM 5.01 Inhibition of CYP2D6 21256008

Literature References

PubMed DOI Target Context # Activities
17118654 10.1016/j.bmcl.2006.10.084 C-C chemokine receptor type 5 2
21256008 10.1016/j.bmcl.2010.12.109 C-C chemokine receptor type 5 2
21256008 10.1016/j.bmcl.2010.12.109 Cytochrome P450 3A4 2
21658961 10.1016/j.bmc.2011.05.022 Liver microsomes 2
21658961 10.1016/j.bmc.2011.05.022 C-C chemokine receptor type 5 2
17118654 10.1016/j.bmcl.2006.10.084 Human immunodeficiency virus 1
17118654 10.1016/j.bmcl.2006.10.084 Human immunodeficiency virus 1 1
17118654 10.1016/j.bmcl.2006.10.084 Rattus norvegicus 1
17118654 10.1016/j.bmcl.2006.10.084 No relevant target 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 No relevant target 1

Data from ChEMBL 36 via Core Engine