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Compound Detail

CHEMBL469146

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Cc1ccc(-n2nccn2)c(C(=O)N2CCCN(c3ncc4ccccc4n3)CC2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL469146
Phase Preclinical
Structure Type MOL
InChI Key AHMDYOOHWSZVAL-UHFFFAOYSA-N
2
Targets
15
Activities
2
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

413.5
MW (Da)
2.87
ALogP
7
HBA
0
HBD
80.0
PSA (Ų)
0.51
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H23N7O
MW 413.49
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -1.71

Activity Summary

Ki 9 meas. best 9.23
IC50 6 meas. best 7.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Orexin receptor type 2
CHEMBL4792
 Ki 9.23 9.2225 0.6 4
Orexin/Hypocretin receptor type 1
CHEMBL5113
 Ki 8.92 8.92 1.2 5
Orexin receptor type 2
CHEMBL4792
 IC50 7.57 7.57 27.0 3
Orexin/Hypocretin receptor type 1
CHEMBL5113
 IC50 7.54 7.54 29.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 78.56 ng.hr.mL-1 Rattus norvegicus
AUC 181.94 ng.hr.mL-1 Canis lupus familiaris
AUC 620.24 ng.hr.mL-1 Rattus norvegicus
AUC 748.42 ng.hr.mL-1 Canis lupus familiaris
AUC 181.94 ng.hr.mL-1 Canis lupus familiaris
AUC 78.56 ng.hr.mL-1 Rattus norvegicus
CL 53.0 mL.min-1.kg-1 Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Canis lupus familiaris
CL 52.6 mL.min-1.kg-1 Rattus norvegicus
CL 11.6 mL.min-1.kg-1 Canis lupus familiaris
CL 11.6 mL.min-1.kg-1 Canis lupus familiaris
CL 12.0 mL.min-1.kg-1 Canis lupus familiaris
CL 53.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 300.0 nM Rattus norvegicus
Cmax 230.0 nM Canis lupus familiaris
Cmax 650.0 nM Rattus norvegicus
Cmax 1440.0 nM Canis lupus familiaris
Cmax 230.0 nM Canis lupus familiaris
Cmax 300.0 nM Rattus norvegicus
F 2.0 % Rattus norvegicus
F 16.0 % Canis lupus familiaris
F 2.0 % Rattus norvegicus
F 16.0 % Canis lupus familiaris
F 16.0 % Canis lupus familiaris
F 16.0 % Canis lupus familiaris
F 2.0 % Rattus norvegicus
T1/2 0.3 hr Rattus norvegicus
T1/2 1.3 hr Canis lupus familiaris
T1/2 0.35 hr Rattus norvegicus
T1/2 1.28 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Orexin receptor type 2 Ki = 0.59 nM 9.23 Displacement of [3H](S)-N-(2-(1H-pyrrol-1-yl)phenyl)-1-(2-(1-methyl-1H-benzo[d]i... 20565075
Orexin receptor type 2 Ki = 0.6 nM 9.22 Binding affinity to OX2 receptor 19406641
Orexin receptor type 2 Ki = 0.6 nM 9.22 Binding affinity to OX2 receptor by radioligand displacement assay 20207138
Orexin receptor type 2 Ki = 0.6 nM 9.22 Binding affinity to OX2R 20610153
Orexin/Hypocretin receptor type 1 Ki = 1.2 nM 8.92 Binding affinity to OX1 receptor 19406641
Orexin/Hypocretin receptor type 1 Ki = 1.2 nM 8.92 Binding affinity to OX1 receptor by radioligand displacement assay 20207138
Orexin/Hypocretin receptor type 1 Ki = 1.2 nM 8.92 Displacement of [3H](S)-N-(biphenyl-2-yl)-1-(2-(1-methyl-1H-benzo[d]imidazol-2-y... 20565075
Orexin/Hypocretin receptor type 1 Ki = 1.2 nM 8.92 Displacement of [3H]N-cyclobutyl-5-methyl-N-(2-(1-methyl-1H-benzo[d]imidazol-2-y... 20565075
Orexin/Hypocretin receptor type 1 Ki = 1.2 nM 8.92 Binding affinity to OX1R 20610153
Orexin receptor type 2 IC50 = 27.0 nM 7.57 Antagonist activity at OX2 receptor assessed as inhibition of calcium flux by FL... 20207138
Orexin receptor type 2 IC50 = 27.0 nM 7.57 Antagonist activity at human OX2R expressed in CHO cells assessed as inhibition ... 20565075
Orexin receptor type 2 IC50 = 27.0 nM 7.57 Antagonist activity at OX2R (unknown origin) 26317591
Orexin/Hypocretin receptor type 1 IC50 = 29.0 nM 7.54 Antagonist activity at OX1 receptor assessed as inhibition of calcium flux by FL... 20207138
Orexin/Hypocretin receptor type 1 IC50 = 29.0 nM 7.54 Antagonist activity at human OX1R expressed in CHO cells assessed as inhibition ... 20565075
Orexin/Hypocretin receptor type 1 IC50 = 29.0 nM 7.54 Antagonist activity at OX1R (unknown origin) 26317591

Literature References

PubMed DOI Target Context # Activities
20565075 10.1021/jm100541c Rattus norvegicus 10
20565075 10.1021/jm100541c Canis familiaris 8
20207138 10.1016/j.bmcl.2010.01.138 Rattus norvegicus 6
20610153 10.1016/j.bmcl.2010.05.047 Rattus norvegicus 5
20610153 10.1016/j.bmcl.2010.05.047 Canis familiaris 5
20207138 10.1016/j.bmcl.2010.01.138 Canis familiaris 5
20565075 10.1021/jm100541c Orexin/Hypocretin receptor type 1 3
20207138 10.1016/j.bmcl.2010.01.138 Orexin/Hypocretin receptor type 1 2
20207138 10.1016/j.bmcl.2010.01.138 Orexin receptor type 2 2
20565075 10.1021/jm100541c Orexin receptor type 2 2
20207138 10.1016/j.bmcl.2010.01.138 No relevant target 1
26317591 10.1021/acs.jmedchem.5b00832 Orexin/Hypocretin receptor type 1 1
20610153 10.1016/j.bmcl.2010.05.047 Orexin receptor type 2 1
20565075 10.1021/jm100541c Liver microsomes 1
19406641 10.1016/j.bmcl.2009.04.026 Orexin/Hypocretin receptor type 1 1
20207138 10.1016/j.bmcl.2010.01.138 Homo sapiens 1
20207138 10.1016/j.bmcl.2010.01.138 ADMET 1
20207138 10.1016/j.bmcl.2010.01.138 Cerebrospinal fluid 1
20207138 10.1016/j.bmcl.2010.01.138 Brain 1
20207138 10.1016/j.bmcl.2010.01.138 Plasma 1

Data from ChEMBL 36 via Core Engine