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Compound Detail

CHEMBL3091687

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NCCCCN(C[C@H]1Cc2ccccc2CN1)[C@H]1CCCc2cccnc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3091687
Phase Preclinical
Structure Type MOL
InChI Key MYCKNKHATQGHEV-YADHBBJMSA-N
11
Targets
37
Activities
1
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

364.5
MW (Da)
3.21
ALogP
4
HBA
2
HBD
54.2
PSA (Ų)
0.74
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H32N4
MW 364.54
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.06

Activity Summary

IC50 37 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-X-C chemokine receptor type 4
CHEMBL2107
 IC50 8.52 7.3863 3.0 19
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.3 7.96 5.0 2
Unchecked
CHEMBL612545
 IC50 8.2 8.2 6.3 1
Cytochrome P450 2D6
CHEMBL289
 IC50 6.5 6.5 320.0 5
Kappa-type opioid receptor
CHEMBL237
 IC50 5.8 5.8 1600.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 5.43 5.43 3700.0 2
D(2) dopamine receptor
CHEMBL217
 IC50 5.24 5.24 5700.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 5.12 5.12 7600.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.05 5.05 8900.0 2
Mu-type opioid receptor
CHEMBL233
 IC50 4.83 4.825 14900.0 2
Alpha-2C adrenergic receptor
CHEMBL1916
 IC50 4.64 4.64 23000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 328.0 ng.hr.mL-1 Rattus norvegicus
AUC 108.0 ng.hr.mL-1 Rattus norvegicus
CL 20.0 mL.min-1.g-1 Homo sapiens
CL 35.0 mL.min-1.g-1 Rattus norvegicus
CL 64.0 mL.min-1.g-1 Mus musculus
F 63.0 % Rattus norvegicus
F 63.0 % Rattus norvegicus
T1/2 6.0 hr Rattus norvegicus
T1/2 1.2 hr Rattus norvegicus
T1/2 1.0 hr Homo sapiens
T1/2 0.65 hr Rattus norvegicus
T1/2 0.3667 hr Mus musculus
T1/2 1.0 hr Homo sapiens
T1/2 6.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-X-C chemokine receptor type 4 IC50 = 3.0 nM 8.52 Antagonist activity at CXCR4 in human Chem-1 cells assessed as inhibition of SDF... 24936240
C-X-C chemokine receptor type 4 IC50 = 5.0 nM 8.3 Antagonist activity at CXCR4 in human MAGI-CCR5 cells assessed as inhibition of ... 24936240
Human immunodeficiency virus 1 IC50 = 5.0 nM 8.3 Antiviral activity against CXCR4 tropic HIV1 3B infected in human MAGI-CCR5/CXCR... 30655949
C-X-C chemokine receptor type 4 IC50 = 6.0 nM 8.22 Antagonist activity at CXCR4 in human CCRF-CEM cells assessed as inhibition of S... 29795757
C-X-C chemokine receptor type 4 IC50 = 6.25 nM 8.2 Antagonist activity at human CXCR4 in CCRF-CEM cells assessed as decrease in SDF... 29350534
C-X-C chemokine receptor type 4 IC50 = 6.25 nM 8.2 Antagonist activity at CXCR4 in human CCRF-CEM cells assessed as inhibition of S... 30052039
C-X-C chemokine receptor type 4 IC50 = 6.25 nM 8.2 Antagonist activity at CXCR4 receptor in human CCRF-CEM cells assessed as inhibi... 34676043
Unchecked IC50 = 6.3 nM 8.2 Antagonist activity at human CXCR4 receptor expressed in CCRF-CEM cells assessed... 35179893
C-X-C chemokine receptor type 4 IC50 = 7.0 nM 8.15 Antagonist activity at CXCR4 in human CCRF-CEM cells assessed as inhibition of S... 29348805
C-X-C chemokine receptor type 4 IC50 = 15.0 nM 7.82 Antagonist activity at CXCR4 (unknown origin) assessed as inhibition of SDF-1-in... 24936240
C-X-C chemokine receptor type 4 IC50 = 19.0 nM 7.72 Antagonist activity at CXCR4 (unknown origin) expressed in CHO-K1 cells assessed... 24936240
Human immunodeficiency virus 1 IC50 = 24.0 nM 7.62 Antiviral activity against HIV1 3B infected in PBMC 25935642
C-X-C chemokine receptor type 4 IC50 = 35.0 nM 7.46 Antagonist activity at CXCR4 in human PBMC assessed as inhibition of HIV-1 3B in... 24936240
C-X-C chemokine receptor type 4 IC50 = 66.0 nM 7.18 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
C-X-C chemokine receptor type 4 IC50 = 91.0 nM 7.04 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
C-X-C chemokine receptor type 4 IC50 = 112.0 nM 6.95 Displacement of [125I]-SDF-1 from CXCR4 (unknown origin) 25935642
C-X-C chemokine receptor type 4 IC50 = 120.0 nM 6.92 Displacement of [125I]SDF-1alpha from CXCR4 in human Chem-1 cells after 90 mins 24936240
C-X-C chemokine receptor type 4 IC50 = 152.0 nM 6.82 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
C-X-C chemokine receptor type 4 IC50 = 197.0 nM 6.71 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
C-X-C chemokine receptor type 4 IC50 = 288.0 nM 6.54 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949

Literature References

PubMed DOI Target Context # Activities
24936240 10.1021/ml400183q C-X-C chemokine receptor type 4 8
30655949 10.1021/acsmedchemlett.8b00441 C-X-C chemokine receptor type 4 7
30655949 10.1021/acsmedchemlett.8b00441 Unchecked 6
35179893 10.1021/acs.jmedchem.1c01564 ADMET 6
24936240 10.1021/ml400183q Mus musculus 5
24936240 10.1021/ml400183q Rattus norvegicus 5
29350534 10.1021/acs.jmedchem.7b01420 Unchecked 5
24936240 10.1021/ml400183q Plasma 4
24936240 10.1021/ml400183q Liver microsome 4
24936240 10.1021/ml400183q ADMET 4
29795757 10.1021/acsmedchemlett.8b00030 Unchecked 3
29350534 10.1021/acs.jmedchem.7b01420 C-X-C chemokine receptor type 4 3
29348805 10.1021/acsmedchemlett.7b00381 ADMET 3
29350534 10.1021/acs.jmedchem.7b01420 Liver 3
29795757 10.1021/acsmedchemlett.8b00030 ADMET 3
34676043 10.1021/acsmedchemlett.1c00449 ADMET 3
29348805 10.1021/acsmedchemlett.7b00381 Cytochrome P450 2D6 2
29795757 10.1021/acsmedchemlett.8b00030 C-X-C chemokine receptor type 4 2
29348805 10.1021/acsmedchemlett.7b00381 No relevant target 2
30052039 10.1021/acs.jmedchem.8b00450 ADMET 2

Data from ChEMBL 36 via Core Engine