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Compound Detail

CHEMBL236902

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C[C@H]1CN(c2ccc(C(=O)Nc3ccccc3N)cn2)CCN1C(=O)OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL236902
Phase Preclinical
Structure Type MOL
InChI Key UQKHQHYWAJFGDY-SFHVURJKSA-N
9
Targets
12
Activities
2
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

445.5
MW (Da)
3.76
ALogP
6
HBA
2
HBD
100.8
PSA (Ų)
0.58
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H27N5O3
MW 445.52
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -1.52

Activity Summary

IC50 11 meas. best 7.14
EC50 1 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 7.14 7.12 73.0 2
Histone deacetylase 2
CHEMBL1937
 IC50 6.57 6.54 272.0 2
Histone deacetylase 3
CHEMBL1829
 IC50 6.03 6.03 939.0 2
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 5.78 5.78 1680.0 1
HCT-116
CHEMBL394
 EC50 5.57 5.57 2700.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.51 5.51 3120.0 1
MAP kinase-activated protein kinase 3
CHEMBL4670
 IC50 5.34 5.34 4520.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 4.78 4.78 16720.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.61 4.61 24500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 0.23 uM.hr.Kg/mg Rattus norvegicus
AUC 3.7 uM.hr.Kg/mg Canis lupus familiaris
AUC 0.23 uM.hr.Kg/mg Rattus norvegicus
AUC 3.8 uM.hr.Kg/mg Canis lupus familiaris
CL 52.0 mL.min-1.kg-1 Rattus norvegicus
CL 7.3 mL.min-1.kg-1 Canis lupus familiaris
CL 52.0 mL.min-1.kg-1 Rattus norvegicus
CL 7.4 mL.min-1.kg-1 Canis lupus familiaris
F 32.0 % Rattus norvegicus
F 73.0 % Canis lupus familiaris
F 73.0 % Canis lupus familiaris
F 37.0 % Rattus norvegicus
T1/2 2.2 hr Rattus norvegicus
T1/2 5.3 hr Canis lupus familiaris
T1/2 0.93 hr Rattus norvegicus
T1/2 5.6 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 73.0 nM 7.14 Inhibition of recombinant HDAC1 17761416
Histone deacetylase 1 IC50 = 79.0 nM 7.1 Inhibition of human HDAC1 expressed in mammalian cells 18951790
Histone deacetylase 2 IC50 = 272.0 nM 6.57 Inhibition of recombinant HDAC2 17761416
Histone deacetylase 2 IC50 = 308.0 nM 6.51 Inhibition of human HDAC2 expressed in mammalian cells 18951790
Histone deacetylase 3 IC50 = 939.0 nM 6.03 Inhibition of recombinant HDAC3 17761416
Histone deacetylase 3 IC50 = 942.0 nM 6.03 Inhibition of human HDAC3 expressed in mammalian cells 18951790
Sodium-dependent serotonin transporter IC50 = 1680.0 nM 5.78 Activity against human serotonin transporter 17761416
HCT-116 EC50 = 2700.0 nM 5.57 Effect on histone H2BK5 acetylation in HCT116 cells after 24 hrs by ELISA 17761416
Sodium-dependent dopamine transporter IC50 = 3120.0 nM 5.51 Activity against human dopamine transporter 17761416
MAP kinase-activated protein kinase 3 IC50 = 4520.0 nM 5.34 Activity against human MAPK3 17761416
Histone deacetylase 8 IC50 = 16720.0 nM 4.78 Inhibition of recombinant HDAC8 17761416
Cytochrome P450 2C9 IC50 = 24500.0 nM 4.61 Inhibition of CYP2C9 17761416

Literature References

PubMed DOI Target Context # Activities
18951790 10.1016/j.bmcl.2008.10.052 Rattus norvegicus 5
18951790 10.1016/j.bmcl.2008.10.052 Canis familiaris 5
17761416 10.1016/j.bmcl.2007.08.023 Canis familiaris 5
17761416 10.1016/j.bmcl.2007.08.023 Rattus norvegicus 5
17761416 10.1016/j.bmcl.2007.08.023 HCT-116 4
17761416 10.1016/j.bmcl.2007.08.023 Unchecked 3
17761416 10.1016/j.bmcl.2007.08.023 ADMET 2
17761416 10.1016/j.bmcl.2007.08.023 Plasma 2
17761416 10.1016/j.bmcl.2007.08.023 Histone deacetylase 8 1
17761416 10.1016/j.bmcl.2007.08.023 HeLa 1
17761416 10.1016/j.bmcl.2007.08.023 Histone deacetylase 6 1
17761416 10.1016/j.bmcl.2007.08.023 Histone deacetylase 3 1
17761416 10.1016/j.bmcl.2007.08.023 Voltage-gated inwardly rectifying potassium channel KCNH2 1
17761416 10.1016/j.bmcl.2007.08.023 Cytochrome P450 3A4 1
17761416 10.1016/j.bmcl.2007.08.023 Cytochrome P450 2C9 1
17761416 10.1016/j.bmcl.2007.08.023 MAP kinase-activated protein kinase 3 1
17761416 10.1016/j.bmcl.2007.08.023 Sodium-dependent dopamine transporter 1
17761416 10.1016/j.bmcl.2007.08.023 Sodium-dependent serotonin transporter 1
17761416 10.1016/j.bmcl.2007.08.023 Cytochrome P450 2D6 1
17761416 10.1016/j.bmcl.2007.08.023 Histone deacetylase 2 1

Data from ChEMBL 36 via Core Engine