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Compound Detail

CHEMBL339053

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O=C(N[C@H](Cc1ccc(Cl)cc1)C(=O)N1CCC(Cn2cncn2)(C2CCCCC2)CC1)[C@H]1Cc2ccccc2CN1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL339053
Phase Preclinical
Structure Type MOL
InChI Key HLCHESOMJVGDSJ-LOYHVIPDSA-N
9
Targets
83
Activities
3
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

589.2
MW (Da)
4.56
ALogP
6
HBA
2
HBD
92.2
PSA (Ų)
0.40
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C33H41ClN6O2
MW 589.18
Aromatic Rings 3
Heavy Atoms 42
NP-Likeness -0.53

Activity Summary

EC50 39 meas. best 9.21
Ki 26 meas. best 10.3
IC50 18 meas. best 9.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Melanocortin receptor 4
CHEMBL259
 Ki 10.3 7.8825 0.1 16
Melanocortin receptor 4
CHEMBL2700
 IC50 9.22 9.22 0.6 1
Melanocortin receptor 4
CHEMBL259
 EC50 9.21 8.4789 0.6 19
Melanocortin receptor 4
CHEMBL259
 IC50 8.92 8.775 1.2 6
Unchecked
CHEMBL612545
 EC50 8.68 6.4875 2.1 4
Melanocortin receptor 4
CHEMBL2700
 EC50 8.54 8.54 2.9 1
Melanocyte-stimulating hormone receptor
CHEMBL3795
 EC50 8.3 6.3075 5.0 4
Melanocortin receptor 4
CHEMBL3719
 EC50 8.12 8.12 7.6 1
Melanocortin receptor 3
CHEMBL4644
 Ki 6.9 6.005 125.0 4
Melanocortin receptor 3
CHEMBL4644
 EC50 6.8 5.89 160.0 5
Melanocyte-stimulating hormone receptor
CHEMBL3795
 Ki 6.52 6.1533 300.0 3
Melanocortin receptor 5
CHEMBL4608
 IC50 6.49 6.49 326.0 3
Melanocortin receptor 5
CHEMBL4608
 EC50 6.13 5.99 736.0 4
Melanocortin receptor 3
CHEMBL4644
 IC50 6.12 6.12 761.0 3
Melanocortin receptor 5
CHEMBL4608
 Ki 6.07 5.685 860.0 2
Melanocortin receptor 3
CHEMBL4023
 EC50 5.88 5.88 1325.0 1
Melanocortin receptor 5
CHEMBL2701
 IC50 5.8 5.8 1575.0 1
Melanocortin receptor 3
CHEMBL4023
 IC50 5.72 5.72 1883.0 1
Melanocyte-stimulating hormone receptor
CHEMBL3795
 IC50 5.69 5.6867 2063.0 3

Pharmacokinetic Data

Parameter Value Units Species
CL 84.0 mL.min-1.kg-1 Rattus norvegicus
CL 27.55 mL.min-1.kg-1 Canis lupus familiaris
CL 27.54 uL.min-1.(10^6cells)-1 Homo sapiens
CL 40.74 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 14.0 % Rattus norvegicus
F 16.0 % Canis lupus familiaris
T1/2 0.6 hr Rattus norvegicus
T1/2 1.2 hr Canis lupus familiaris
Tmax 1.0 hr -
Tmax 1.5 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Melanocortin receptor 4 Ki = 0.05 nM 10.3 Binding affinity towards Melanocortin 4 receptor using [125I]NDP-MSH 15317471
Melanocortin receptor 4 IC50 = 0.6 nM 9.22 Evaluated for binding affinity against rat Melanocortin-4 receptor (rMC4R) by di... 12361385
Melanocortin receptor 4 EC50 = 0.61 nM 9.21 Agonist activity at the mutant MC4R Y287F expressed in HEK293 cells by cAMP accu... 16451057
Melanocortin receptor 4 EC50 = 0.71 nM 9.15 Agonist activity at the mutant MC4R F184A expressed in HEK293 cells by cAMP accu... 16451057
Melanocortin receptor 4 EC50 = 0.82 nM 9.09 Agonist activity at the mutant MC4R Y268A expressed in HEK293 cells by cAMP accu... 16451057
Melanocortin receptor 4 EC50 = 1.0 nM 9.0 Agonist activity at human MC4 receptor expressed in HEK293 cells 18078748
Melanocortin receptor 4 IC50 = 1.2 nM 8.92 Displacement of [125]NDP-MSH from human MC4 receptor expressed in HEK293 cells 15615531
Melanocortin receptor 4 IC50 = 1.2 nM 8.92 Displacement of [125I]NDP-alpha-MSH from human MC4R expressed in CHO cells 16364639
Melanocortin receptor 4 IC50 = 1.2 nM 8.92 Concentration required for 50% inhibition by displacement of of [125I]NDP-alpha-... 15951175
Melanocortin receptor 4 IC50 = 1.2 nM 8.92 Evaluated for binding affinity against Melanocortin-4 receptor by displacing [12... 12361385
Melanocortin receptor 4 IC50 = 1.2 nM 8.92 Evaluated for binding affinity against human Melanocortin-4 receptor (hMC4R) by ... 12361385
Melanocortin receptor 4 EC50 = 1.2 nM 8.92 Agonist activity at the human wild type MC4R expressed in HEK293 cells by cAMP a... 16451057
Melanocortin receptor 4 EC50 = 1.45 nM 8.84 Agonist activity at human MC4 receptor expressed in HEK293 cells assessed as sti... 15615531
Melanocortin receptor 4 EC50 = 1.5 nM 8.82 Agonist activity at the mutant MC4R Y268F expressed in HEK293 cells by cAMP accu... 16451057
Melanocortin receptor 4 EC50 = 2.1 nM 8.68 Functional activity as concentration at 50% maximum cAMP accumulation in human M... 12361385
Melanocortin receptor 4 EC50 = 2.1 nM 8.68 Activity against human MC4R by cAMP accumulation 16364639
Unchecked EC50 = 2.1 nM 8.68 Effective dose against cAMP accumulation 15951175
Melanocortin receptor 4 EC50 = 2.1 nM 8.68 Agonist activity at human MC4 receptor 18078748
Melanocortin receptor 4 EC50 = 2.1 nM 8.68 Evaluated for Functional Activity at Melanocortin-4 receptor as effective concen... 12361385
Melanocortin receptor 4 EC50 = 2.9 nM 8.54 Functional activity as concentration at 50% maximum cAMP accumulation in rat Mel... 12361385

Literature References

PubMed DOI Target Context # Activities
16451057 10.1021/jm050780s Melanocortin receptor 4 30
12361385 10.1021/jm025539h Melanocortin receptor 4 9
15951175 10.1016/j.bmcl.2005.05.012 Unchecked 8
12361385 10.1021/jm025539h Melanocortin receptor 3 8
12361385 10.1021/jm025539h Melanocortin receptor 5 8
15615531 10.1021/jm049278i Melanocortin receptor 4 7
12361385 10.1021/jm025539h ADMET 6
- 10.6019/CHEMBL3301361 ADMET 4
14552781 10.1016/s0960-894x(03)00796-0 Melanocortin receptor 4 3
15357964 10.1016/j.bmcl.2004.06.059 Melanocortin receptor 4 3
16364639 10.1016/j.bmcl.2005.11.095 Melanocortin receptor 3 3
16364639 10.1016/j.bmcl.2005.11.095 Melanocyte-stimulating hormone receptor 3
16364639 10.1016/j.bmcl.2005.11.095 Melanocortin receptor 4 3
16364639 10.1016/j.bmcl.2005.11.095 Melanocortin receptor 5 3
18078748 10.1016/j.bmcl.2007.11.109 Melanocortin receptor 4 3
12361385 10.1021/jm025539h Melanocyte-stimulating hormone receptor 3
18078748 10.1016/j.bmcl.2007.11.109 Unchecked 2
12361385 10.1021/jm025539h Canis familiaris 2
15317471 10.1021/jm0311285 Melanocortin receptor 4 2
12361385 10.1021/jm025539h Melanocortin receptor (M3 and M4) 2

Data from ChEMBL 36 via Core Engine