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Compound Detail

CHEMBL311795

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Cc1ncnc(C)c1C(=O)N1CCC(C)(N2CCN([C@@H](C)c3ccc(C(F)(F)F)cc3)[C@@H](C)C2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL311795
Phase Preclinical
Structure Type MOL
InChI Key HMBFXHIQISYDKM-RXVVDRJESA-N
7
Targets
21
Activities
2
Assay Types
12
PK Parameters
13
Publications
0
Known Names

Molecular Properties

503.6
MW (Da)
4.87
ALogP
5
HBA
0
HBD
52.6
PSA (Ų)
0.60
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H36F3N5O
MW 503.61
Aromatic Rings 2
Heavy Atoms 36
NP-Likeness -0.79

Activity Summary

IC50 13 meas. best 11.0
Ki 8 meas. best 8.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-C chemokine receptor type 5
CHEMBL274
 IC50 11.0 11.0 0.0 1
ADMET
CHEMBL612558
 IC50 9.7 8.226 0.2 10
Unchecked
CHEMBL612545
 IC50 9.41 9.41 0.4 1
U-87 MG
CHEMBL614247
 IC50 9.3 9.3 0.5 1
C-C chemokine receptor type 5
CHEMBL274
 Ki 8.55 8.53 2.8 3
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 6.34 6.3067 456.0 3
Muscarinic acetylcholine receptor M1
CHEMBL216
 Ki 6.24 6.24 575.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
 Ki 6.14 6.14 716.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6210.0 ng.hr.mL-1 Rattus norvegicus
AUC 22700.0 ng.hr.mL-1 Rattus norvegicus
AUC 22000.0 ng.hr.mL-1 Rattus norvegicus
AUC 4710.0 ng.hr.mL-1 Cercopithecidae
AUC 2370.0 ng.hr.mL-1 Cercopithecidae
AUC 6210.0 ng.hr.mL-1 Rattus norvegicus
Cmax 2958.64 nM Rattus norvegicus
Cmax 675.13 nM Cercopithecidae
F 97.0 % Rattus norvegicus
F 50.0 % Cercopithecidae
T1/2 22.0 hr Rattus norvegicus
T1/2 8.0 hr Cercopithecidae

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-C chemokine receptor type 5 IC50 = 0.01 nM 11.0 Inhibition of 0.1 nM of MIP-1beta induced migration of recombinant mouse pro-B c... 12565973
ADMET IC50 = 0.2 nM 9.7 Compound was tested for inhibition of HIV isolate ASM 108 (hz) in peripheral blo... 12565973
Unchecked IC50 = 0.39 nM 9.41 Compound was tested for inhibiting the entry of replication deffective HIV-1 (YU... 15115380
U-87 MG IC50 = 0.5 nM 9.3 Tested for inhibiting HIV (ADA) entry into cells 12565973
ADMET IC50 = 0.7 nM 9.15 Compound was tested for inhibition of HIV isolate US-1 in peripheral blood monon... 12565973
ADMET IC50 = 1.3 nM 8.89 Compound was tested for inhibition of HIV isolate YU-2 (hz) in peripheral blood ... 12565973
ADMET IC50 = 2.3 nM 8.64 Compound was tested for inhibition of HIV isolate YU-2 (wt) in peripheral blood ... 12565973
C-C chemokine receptor type 5 Ki = 2.8 nM 8.55 Antagonistic activity against C-C chemokine receptor type 5 15115380
C-C chemokine receptor type 5 Ki = 3.0 nM 8.52 Inhibition of RANTES binding to the human C-C chemokine receptor type 5 (CCR5) 14521412
C-C chemokine receptor type 5 Ki = 3.0 nM 8.52 Ability of compound to inhibit [125I]-labeled RANTES binding to the CCR5 recepto... 12565973
ADMET IC50 = 3.2 nM 8.49 Compound was tested for inhibition of HIV isolate 301657 (wt) in peripheral bloo... 12565973
ADMET IC50 = 6.4 nM 8.19 Compound was tested for inhibition of HIV isolate bal (hz) in peripheral blood m... 12565973
ADMET IC50 = 7.0 nM 8.15 Compound was tested for inhibition of HIV isolate ASM 108 (wt) in peripheral blo... 12565973
ADMET IC50 = 26.8 nM 7.57 Compound was tested for inhibition of HIV isolate 301657 (hz) in peripheral bloo... 12565973
ADMET IC50 = 166.0 nM 6.78 Compound was tested for inhibition of HIV isolate JV 1083 in peripheral blood mo... 12565973
ADMET IC50 = 200.0 nM 6.7 Compound was tested for inhibition of HIV isolate BCF01 in peripheral blood mono... 12565973
Muscarinic acetylcholine receptor M2 Ki = 456.0 nM 6.34 Inhibition of binding affinity to muscarinic receptor M2 12565973
Muscarinic acetylcholine receptor M2 Ki = 456.0 nM 6.34 Antagonistic activity against Muscarinic acetylcholine receptor M2 15115380
Muscarinic acetylcholine receptor M2 Ki = 575.0 nM 6.24 Binding affinity towards muscarinic receptor M2 12565973
Muscarinic acetylcholine receptor M1 Ki = 575.0 nM 6.24 Antagonistic activity against muscarinic M1 receptor 15115380

Literature References

PubMed DOI Target Context # Activities
12565973 10.1016/s0960-894x(02)00918-6 ADMET 25
12565973 10.1016/s0960-894x(02)00918-6 Rattus norvegicus 7
15115380 10.1021/jm0304515 ADMET 5
12565973 10.1016/s0960-894x(02)00918-6 C-C chemokine receptor type 5 2
12565973 10.1016/s0960-894x(02)00918-6 Muscarinic acetylcholine receptor M2 2
12565973 10.1016/s0960-894x(02)00918-6 U-87 MG 1
15115380 10.1021/jm0304515 C-C chemokine receptor type 5 1
15115380 10.1021/jm0304515 Muscarinic acetylcholine receptor M1 1
15115380 10.1021/jm0304515 Muscarinic acetylcholine receptor M2 1
15115380 10.1021/jm0304515 Muscarinic acetylcholine receptor M3 1
15115380 10.1021/jm0304515 Unchecked 1
15115380 10.1021/jm0304515 Rattus norvegicus 1
14521412 10.1021/jm030265z C-C chemokine receptor type 5 1

Data from ChEMBL 36 via Core Engine