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Compound Detail

CHEMBL122226

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Cc1ccc(CN2CCCNCCNCCCNCC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL122226
Phase Preclinical
Structure Type MOL
InChI Key YYKNLRGFDMOOFB-UHFFFAOYSA-N
3
Targets
21
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

304.5
MW (Da)
1.36
ALogP
4
HBA
3
HBD
39.3
PSA (Ų)
0.77
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H32N4
MW 304.48
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness -0.83

Activity Summary

Ki 19 meas. best 6.77
EC50 2 meas. best 5.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-X-C chemokine receptor type 4
CHEMBL2107
 Ki 6.77 4.968 170.0 15
Human immunodeficiency virus 2
CHEMBL380
 EC50 5.94 5.94 1146.2 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 5.85 5.85 1416.9 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-X-C chemokine receptor type 4 Ki = 170.0 nM 6.77 Binding affinity to CXCR4 (unknown origin) assessed as inhibition constant 28165741
Human immunodeficiency virus 2 EC50 = 1146.2 nM 5.94 Concentration required to protect the virus infected cells against viral cytopat... 7830280
Human immunodeficiency virus 1 EC50 = 1416.9 nM 5.85 Concentration required to protect the virus infected cells against viral cytopat... 7830280
C-X-C chemokine receptor type 4 Ki = 2300.0 nM 5.64 Antagonist activity at human CXCR4 I284A mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 2500.0 nM 5.6 Antagonist activity at transmembrane domain 6 of human CXCR4 I259A mutant expres... 17599916
C-X-C chemokine receptor type 4 Ki = 2900.0 nM 5.54 Antagonist activity at human CXCR4 D262N mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 3300.0 nM 5.48 Antagonist activity at human CXCR4 T287A mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 13000.0 nM 4.89 Antagonist activity at human CXCR4 L120F mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 15000.0 nM 4.82 Antagonist activity at human CXCR4 F172A mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 20000.0 nM 4.7 Antagonist activity at human wild type CXCR4 expressed in COS7 cells coexpressin... 17599916
C-X-C chemokine receptor type 4 Ki = 22000.0 nM 4.66 Antagonist activity at human CXCR4 H281A mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 24000.0 nM 4.62 Antagonist activity at human CXCR4 I259W mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 28000.0 nM 4.55 Antagonist activity at human CXCR4 V196A mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 32000.0 nM 4.5 Antagonist activity at human CXCR4 H203A mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 37000.0 nM 4.43 Antagonist activity at human CXCR4 Y255A mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 60000.0 nM 4.22 Antagonist activity at human CXCR4 Q200W mutant expressed in COS7 cells coexpres... 17599916
C-X-C chemokine receptor type 4 Ki = 80000.0 nM 4.1 Antagonist activity at human CXCR4 Q200A mutant expressed in COS7 cells coexpres... 17599916

Literature References

PubMed DOI Target Context # Activities
17599916 10.1074/jbc.m704739200 C-X-C chemokine receptor type 4 36
7830280 10.1021/jm00002a019 Human immunodeficiency virus 1 1
7830280 10.1021/jm00002a019 Human immunodeficiency virus 2 1
7830280 10.1021/jm00002a019 MT4 1
28165741 10.1021/acs.jmedchem.6b01309 C-X-C chemokine receptor type 4 1

Data from ChEMBL 36 via Core Engine