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Compound Detail

CHEMBL3979678

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C[C@H]1NC(=O)c2cc(-c3cccc4c(=O)n(C)c(NC(C)(C)C)nc34)[nH]c21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3979678
Phase Preclinical
Structure Type MOL
InChI Key HLPARXMUJBJYFM-SNVBAGLBSA-N
11
Targets
20
Activities
3
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

365.4
MW (Da)
2.94
ALogP
5
HBA
3
HBD
91.8
PSA (Ų)
0.65
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H23N5O2
MW 365.44
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.39

Activity Summary

IC50 16 meas. best 9.7
Kd 3 meas. best 8.92
EC50 1 meas. best 6.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase pim-2
CHEMBL4523
 IC50 9.7 9.4 0.2 3
Serine/threonine-protein kinase pim-1
CHEMBL2147
 IC50 9.52 9.3025 0.3 4
Serine/threonine-protein kinase pim-3
CHEMBL5407
 Kd 8.92 8.92 1.2 1
Serine/threonine-protein kinase pim-1
CHEMBL2147
 Kd 8.89 8.89 1.3 1
Serine/threonine-protein kinase pim-2
CHEMBL4523
 Kd 8.77 8.77 1.7 1
EOL1
CHEMBL614489
 IC50 7.7 7.7 20.0 1
Serine/threonine-protein kinase PIM
CHEMBL3559682
 IC50 7.51 7.51 31.0 1
Unchecked
CHEMBL612545
 IC50 7.23 6.525 59.0 2
Mus musculus
CHEMBL375
 EC50 6.59 6.59 254.0 1
KMS-12-BM
CHEMBL4296455
 IC50 6.58 6.58 260.0 2
OPM-2
CHEMBL2366353
 IC50 6.14 6.14 720.0 1
RPMI-8226
CHEMBL614882
 IC50 6.08 6.08 830.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.51 4.51 31000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 19.0 mL.min-1.g-1 Homo sapiens
CL 22.0 mL.min-1.g-1 Rattus norvegicus
CL 5.0 mL.min-1.kg-1 Rattus norvegicus
CL 81.67 mL.min-1.kg-1 Rattus norvegicus
CL 14.0 mL.min-1.g-1 Rattus norvegicus
CL 14.0 mL.min-1.g-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.33 mL.min-1.kg-1 Canis lupus familiaris
CL 121.67 mL.min-1.kg-1 Canis lupus familiaris
F 39.0 % Rattus norvegicus
F 39.0 % Rattus norvegicus
F 44.0 % Canis lupus familiaris
Fu 0.061 - Rattus norvegicus
Fu 0.061 - Rattus norvegicus
Fu 0.079 - Homo sapiens
Fu 0.11 - Canis lupus familiaris
Fu 0.084 - Mus musculus
T1/2 4.6 hr Rattus norvegicus
T1/2 4.6 hr Rattus norvegicus
T1/2 0.7 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase pim-2 IC50 = 0.2 nM 9.7 Inhibition of full length recombinant Pim-2 (unknown origin) assessed as reducti... 27285051
Serine/threonine-protein kinase pim-1 IC50 = 0.3 nM 9.52 Inhibition of full length recombinant Pim-1 (unknown origin) assessed as reducti... 27285051
Serine/threonine-protein kinase pim-1 IC50 = 0.34 nM 9.47 Inhibition of full length recombinant PIM1 (unknown origin) assessed as reductio... 30624936
Serine/threonine-protein kinase pim-2 IC50 = 0.38 nM 9.42 Inhibition of full length recombinant PIM2 (unknown origin) assessed as reductio... 30624936
Serine/threonine-protein kinase pim-1 IC50 = 0.779 nM 9.11 Homogeneous Time Resolved Fluorescence Assay (HTRF): The assay for the determina... -
Serine/threonine-protein kinase pim-1 IC50 = 0.779 nM 9.11 Homogeneous Time Resolved Fluorescence Assay (HTRF): The assay for the determina... -
Serine/threonine-protein kinase pim-2 IC50 = 0.826 nM 9.08 Homogeneous Time Resolved Fluorescence Assay (HTRF): The assay for the determina... -
Serine/threonine-protein kinase pim-3 Kd = 1.2 nM 8.92 Binding affinity to human PIM3 (16 to 317 residues) expressed in bacterial syste... 27285051
Serine/threonine-protein kinase pim-1 Kd = 1.3 nM 8.89 Binding affinity to human PIM1 (15 to 313 residues) expressed in bacterial syste... 27285051
Serine/threonine-protein kinase pim-2 Kd = 1.7 nM 8.77 Binding affinity to human PIM2 (1 to 291 residues) expressed in bacterial system... 27285051
EOL1 IC50 = 20.0 nM 7.7 Antiproliferative activity against human EOL-1 cells after 72 hrs by CellTiter-G... 30624936
Serine/threonine-protein kinase PIM IC50 = 31.0 nM 7.51 Inhibition of pan Pim in human KMS-12-BM cells assessed as reduction in phosphor... 27285051
Unchecked IC50 = 59.0 nM 7.23 Inhibition of PIM1/PIM2/PIM3 in human KMS-12-BM cells assessed as reduction in B... 30624936
Mus musculus EC50 = 254.0 nM 6.59 In vivo inhibition of pan Pim in SCID-bg mouse xenografted with human KMS-12-BM ... 27285051
KMS-12-BM IC50 = 260.0 nM 6.58 Antiproliferative activity against human KMS-12-BM cells after 72 hrs by CellTit... 30624936
KMS-12-BM IC50 = 260.0 nM 6.58 Cytotoxicity against human KMS-12-BM cells assessed as reduction in cell viabili... 27285051
OPM-2 IC50 = 720.0 nM 6.14 Antiproliferative activity against human OPM2 cells after 72 hrs by CellTiter-Gl... 30624936
RPMI-8226 IC50 = 830.0 nM 6.08 Antiproliferative activity against human RPMI8226 cells after 72 hrs by CellTite... 30624936
Unchecked IC50 = 1500.0 nM 5.82 Antiproliferative activity against human OCI-M1 cells after 72 hrs by CellTiter-... 30624936
Cytochrome P450 2C19 IC50 = 31000.0 nM 4.51 Inhibition of CYP2C19 (unknown origin) 27285051

Literature References

PubMed DOI Target Context # Activities
27285051 10.1021/acs.jmedchem.6b00610 ADMET 25
27285051 10.1021/acs.jmedchem.6b00610 Mus musculus 21
30624936 10.1021/acs.jmedchem.8b01733 ADMET 8
27285051 10.1021/acs.jmedchem.6b00610 KMS-12-BM 6
27285051 10.1021/acs.jmedchem.6b00610 Serine/threonine-protein kinase pim-1 3
30624936 10.1021/acs.jmedchem.8b01733 No relevant target 3
27285051 10.1021/acs.jmedchem.6b00610 Serine/threonine-protein kinase pim-2 2
27285051 10.1021/acs.jmedchem.6b00610 No relevant target 2
30624936 10.1021/acs.jmedchem.8b01733 Unchecked 2
30624936 10.1021/acs.jmedchem.8b01733 KMS-12-BM 1
30624936 10.1021/acs.jmedchem.8b01733 RPMI-8226 1
30624936 10.1021/acs.jmedchem.8b01733 OPM-2 1
30624936 10.1021/acs.jmedchem.8b01733 EOL1 1
30624936 10.1021/acs.jmedchem.8b01733 Serine/threonine-protein kinase pim-1 1
27285051 10.1021/acs.jmedchem.6b00610 Serine/threonine-protein kinase PIM 1
27285051 10.1021/acs.jmedchem.6b00610 Cytochrome P450 3A4 1
27285051 10.1021/acs.jmedchem.6b00610 Cytochrome P450 1A2 1
27285051 10.1021/acs.jmedchem.6b00610 Cytochrome P450 2C19 1
27285051 10.1021/acs.jmedchem.6b00610 Cytochrome P450 2D6 1
27285051 10.1021/acs.jmedchem.6b00610 Nuclear receptor subfamily 1 group I member 2 1

Data from ChEMBL 36 via Core Engine