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Compound Detail

CHEMBL5203121

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C[C@H]1OC(=O)N(c2nc(-c3cnc(N)nc3C(F)(F)F)cc(N3CCOCC3)n2)[C@H]1CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5203121
Phase Preclinical
Structure Type MOL
InChI Key GFZKPRZGOZINHQ-SKDRFNHKSA-N
9
Targets
23
Activities
1
Assay Types
30
PK Parameters
12
Publications
0
Known Names

Molecular Properties

455.4
MW (Da)
1.08
ALogP
10
HBA
2
HBD
139.8
PSA (Ų)
0.69
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H20F3N7O4
MW 455.40
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -0.90

Activity Summary

IC50 23 meas. best 8.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
 IC50 8.08 8.08 8.3 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
CHEMBL3145
 IC50 8.08 8.08 8.3 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 IC50 7.92 7.92 12.0 1
Unchecked
CHEMBL612545
 IC50 7.58 7.0453 26.0 15
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL5169092
 IC50 7.38 7.38 42.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
CHEMBL3608198
 IC50 7.19 7.19 65.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
CHEMBL3267
 IC50 6.64 6.64 230.0 1
Serine/threonine-protein kinase mTOR
CHEMBL1255165
 IC50 5.79 5.79 1633.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 5.61 5.61 2474.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 806.06 ng.hr.mL-1 Rattus norvegicus
AUC 20297.18 ng.hr.mL-1 Canis lupus familiaris
AUC 69384.74 ng.hr.mL-1 Canis lupus familiaris
AUC 2504.7 ng.hr.mL-1 Mus musculus
AUC 7286.4 ng.hr.mL-1 Mus musculus
AUC 11840.4 ng.hr.mL-1 Mus musculus
AUC 24591.6 ng.hr.mL-1 Mus musculus
CL 22.0 mL.min-1.kg-1 Rattus norvegicus
CL 10.0 mL.min-1.kg-1 Mus musculus
CL 3.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 422.0 nM Mus musculus
Cmax 1121.0 nM Canis lupus familiaris
Cmax 1244.0 nM Canis lupus familiaris
Cmax 10669.0 nM Canis lupus familiaris
Cmax 1480.0 nM Mus musculus
Cmax 2280.0 nM Mus musculus
Cmax 2910.0 nM Mus musculus
Cmax 8950.0 nM Mus musculus
F 97.0 % Rattus norvegicus
F 49.0 % Mus musculus
F 98.0 % Canis lupus familiaris
F 100.0 % Rattus norvegicus
F 20.0 % Rattus norvegicus
T1/2 9.9 hr Canis lupus familiaris
T1/2 3.3 hr Rattus norvegicus
T1/2 2.0 hr Mus musculus
T1/2 11.0 hr Canis lupus familiaris
T1/2 12.9 hr Canis lupus familiaris
Tmax 0.5 hr Mus musculus
Tmax 1.3 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 8.3 nM 8.08 Inhibition of PI3Kdelta (unknown origin) using phosphatidylinositol as substrate... 35500094
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 8.3 nM 8.08 Inhibition of PI3Kbeta (unknown origin) using L-alpha-phosphatidylinositol as su... 35500094
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 12.0 nM 7.92 Inhibition of PI3Kalpha (unknown origin) using L-alpha-phosphatidylinositol as s... 35500094
Unchecked IC50 = 26.0 nM 7.58 Inhibition of PI3Kdelta in rat Rat1 cells assessed as reduction in phosphorylati... 35500094
Unchecked IC50 = 26.0 nM 7.58 Inhibition of wild type PI3K in human HCC1143 cells assessed as reduction in pho... 35500094
Unchecked IC50 = 27.0 nM 7.57 Inhibition of wild type PI3K in human Hs-578T cells assessed as reduction in pho... 35500094
Unchecked IC50 = 30.0 nM 7.52 Inhibition of wild type PI3K in human CAL-85-1 cells assessed as reduction in ph... 35500094
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 42.0 nM 7.38 Inhibition of PI3Kalpha in rat Rat1 cells assessed as reduction in phosphorylati... 35500094
Unchecked IC50 = 56.0 nM 7.25 Inhibition of PI3K PTEN mutant in human HCC70 cells assessed as reduction in pho... 35500094
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 65.0 nM 7.19 Inhibition of PI3Kbeta in rat Rat1 cells assessed as reduction in phosphorylatio... 35500094
Unchecked IC50 = 88.0 nM 7.06 Inhibition of PI3K PTEN mutant in human HCC38 cells assessed as reduction in pho... 35500094
Unchecked IC50 = 94.0 nM 7.03 Inhibition of wild type PI3K in human HCC1187 cells assessed as reduction in pho... 35500094
Unchecked IC50 = 100.0 nM 7.0 Inhibition of PI3K in human U-87 MG cells assessed as reduction in phosphorylati... 35500094
Unchecked IC50 = 99.0 nM 7.0 Inhibition of PI3K PTEN mutant in human BT-549 cells assessed as reduction in ph... 35500094
Unchecked IC50 = 169.0 nM 6.77 Inhibition of PI3K PTEN mutant in human HCC1395 cells assessed as reduction in p... 35500094
Unchecked IC50 = 179.0 nM 6.75 Inhibition of PI3K PTEN mutant in human MDA-MB-436 cells assessed as reduction i... 35500094
Unchecked IC50 = 200.0 nM 6.7 In vivo Inhibition of AKT phosphorylation at Ser473 residue in plasma of athymic... 35500094
Unchecked IC50 = 204.0 nM 6.69 Inhibition of wild type PI3K in human HCC1806 cells assessed as reduction in pho... 35500094
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform IC50 = 230.0 nM 6.64 Inhibition of PI3Kgamma (unknown origin) using phosphatidylinositol 4,5-bisphosp... 35500094
Unchecked IC50 = 251.0 nM 6.6 Inhibition of PI3K PTEN mutant in human HCC1937 cells assessed as reduction in p... 35500094

Literature References

PubMed DOI Target Context # Activities
35500094 10.1021/acs.jmedchem.2c00267 ADMET 86
35500094 10.1021/acs.jmedchem.2c00267 Unchecked 30
35500094 10.1021/acs.jmedchem.2c00267 No relevant target 8
35500094 10.1021/acs.jmedchem.2c00267 Rat1 8
35500094 10.1021/acs.jmedchem.2c00267 Caco-2 4
35500094 10.1021/acs.jmedchem.2c00267 Serine/threonine-protein kinase mTOR 3
35500094 10.1021/acs.jmedchem.2c00267 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 2
35500094 10.1021/acs.jmedchem.2c00267 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform 2
35500094 10.1021/acs.jmedchem.2c00267 Tubulin 2
35500094 10.1021/acs.jmedchem.2c00267 A2780 1
35500094 10.1021/acs.jmedchem.2c00267 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform 1
35500094 10.1021/acs.jmedchem.2c00267 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform 1

Data from ChEMBL 36 via Core Engine