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Compound Detail

CHEMBL1083358

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C[C@@H]1CCN(c2ncc3cc(F)ccc3n2)CCN1C(=O)c1ccccc1-n1nccn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1083358
Phase Preclinical
Structure Type MOL
InChI Key XBSMDANCGKSKGK-MRXNPFEDSA-N
3
Targets
15
Activities
2
Assay Types
9
PK Parameters
19
Publications
0
Known Names

Molecular Properties

431.5
MW (Da)
3.09
ALogP
7
HBA
0
HBD
80.0
PSA (Ų)
0.50
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 C23H22FN7O
MW 431.48
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -1.73

Activity Summary

IC50 8 meas. best 7.57
Ki 7 meas. best 9.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Orexin receptor type 2
CHEMBL4792
 Ki 9.77 9.4033 0.2 3
Unchecked
CHEMBL612545
 Ki 9.7 9.7 0.2 1
Orexin/Hypocretin receptor type 1
CHEMBL5113
 Ki 8.74 8.74 1.8 3
Orexin receptor type 2
CHEMBL4792
 IC50 7.57 7.57 27.0 4
Orexin/Hypocretin receptor type 1
CHEMBL5113
 IC50 7.57 7.57 27.0 3
Unchecked
CHEMBL612545
 IC50 7.57 7.57 27.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1941.66 ng.hr.mL-1 Rattus norvegicus
CL 33.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.2 mL.min-1.kg-1 Canis lupus familiaris
CL 3.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 2000.0 nM Rattus norvegicus
F 47.0 % Rattus norvegicus
F 37.0 % Canis lupus familiaris
Fu 0.03 - Rattus norvegicus
Tmax 1.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Orexin receptor type 2 Ki = 0.17 nM 9.77 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 = 0.2 nM 9.7 Displacement of [3H]radioligand from human orexin-2 receptor expressed in CHO ce... 24704030
Unchecked Ki = 0.2 nM 9.7 Binding affinity to human orexin 1 receptor Ile408-Val mutant expressed in CHO c... 25613676
Orexin/Hypocretin receptor type 1 Ki = 1.8 nM 8.74 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 = 1.8 nM 8.74 Displacement of [3H]N-cyclobutyl-5-methyl-N-(2-(1-methyl-1H-benzo[d]imidazol-2-y... 20565075
Orexin/Hypocretin receptor type 1 Ki = 1.8 nM 8.74 Displacement of [3H]radioligand from human orexin-1 receptor expressed in CHO ce... 24704030
Orexin receptor type 2 Ki = 1.8 nM 8.74 Binding affinity to human orexin 2 receptor expressed in CHO cells after 3 hrs b... 25613676
Orexin/Hypocretin receptor type 1 IC50 = 27.0 nM 7.57 Antagonist activity at human OX1R expressed in CHO cells assessed as inhibition ... 20565075
Orexin receptor type 2 IC50 = 27.0 nM 7.57 Antagonist activity at human OX2R expressed in CHO cells assessed as inhibition ... 20565075
Orexin/Hypocretin receptor type 1 IC50 = 27.0 nM 7.57 Antagonist activity at human orexin-1 receptor expressed in CHO cells assessed a... 24704030
Orexin receptor type 2 IC50 = 27.0 nM 7.57 Antagonist activity at human orexin-2 receptor expressed in CHO cells assessed a... 24704030
Unchecked IC50 = 27.0 nM 7.57 Antagonist activity at human orexin 1 receptor Ile408-Val mutant expressed in CH... 25613676
Orexin receptor type 2 IC50 = 27.0 nM 7.57 Antagonist activity at human orexin 2 receptor expressed in CHO cells assessed a... 25613676
Orexin receptor type 2 IC50 = 27.0 nM 7.57 Antagonist activity at OX2R (unknown origin) 26317591
Orexin/Hypocretin receptor type 1 IC50 = 27.0 nM 7.57 Antagonist activity at OX1R (unknown origin) 26317591

Literature References

PubMed DOI Target Context # Activities
25613676 10.1016/j.bmcl.2014.12.081 Rattus norvegicus 7
20565075 10.1021/jm100541c Rattus norvegicus 6
24704030 10.1016/j.bmcl.2014.03.052 Rattus norvegicus 4
20565075 10.1021/jm100541c ADMET 3
20565075 10.1021/jm100541c Orexin/Hypocretin receptor type 1 3
24704030 10.1016/j.bmcl.2014.03.052 Orexin receptor type 2 2
25613676 10.1016/j.bmcl.2014.12.081 Liver microsome 2
25613676 10.1016/j.bmcl.2014.12.081 Orexin receptor type 2 2
25613676 10.1016/j.bmcl.2014.12.081 Unchecked 2
24704030 10.1016/j.bmcl.2014.03.052 Liver microsome 2
20565075 10.1021/jm100541c Plasma 2
24704030 10.1016/j.bmcl.2014.03.052 Orexin/Hypocretin receptor type 1 2
20565075 10.1021/jm100541c Canis familiaris 2
20565075 10.1021/jm100541c Orexin receptor type 2 2
20565075 10.1021/jm100541c No relevant target 1
20565075 10.1021/jm100541c Liver microsomes 1
25613676 10.1016/j.bmcl.2014.12.081 Canis familiaris 1
26317591 10.1021/acs.jmedchem.5b00832 Orexin receptor type 2 1
26317591 10.1021/acs.jmedchem.5b00832 Orexin/Hypocretin receptor type 1 1

Data from ChEMBL 36 via Core Engine