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Compound Detail

CHEMBL573107

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CC(C)CCN1c2nc(Nc3cc(F)c(O)c(F)c3)ncc2N(C)C(=O)C1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL573107
Phase Preclinical
Structure Type MOL
InChI Key DTEKTGDVSARYDS-UHFFFAOYSA-N
512
Targets
614
Activities
4
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

391.4
MW (Da)
3.42
ALogP
6
HBA
2
HBD
81.6
PSA (Ų)
0.76
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 C19H23F2N5O2
MW 391.42
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.87

Activity Summary

IC50 604 meas. best 8.52
EC50 4 meas. best 5.72
Kd 4 meas. best 6.21
Ki 2 meas. best 7.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Ribosomal protein S6 kinase alpha-1
CHEMBL2553
 IC50 8.52 7.8467 3.0 3
Ribosomal protein S6 kinase alpha-3
CHEMBL2345
 IC50 8.4 7.3629 4.0 7
Ribosomal protein S6 kinase alpha-2
CHEMBL3906
 IC50 8.0 7.815 10.0 6
Ribosomal protein S6 kinase alpha-6
CHEMBL4924
 IC50 8.0 7.88 10.0 5
Ribosomal protein S6 kinase alpha-1
CHEMBL5528
 IC50 8.0 7.755 10.0 2
Unchecked
CHEMBL612545
 IC50 8.0 7.1767 10.0 3
Serine/threonine-protein kinase VRK2
CHEMBL1649059
 Ki 7.55 7.55 28.0 1
Serine/threonine-protein kinase VRK1
CHEMBL1293199
 IC50 7.48 7.48 33.0 1
EW-3
CHEMBL2366307
 IC50 7.45 7.45 35.8 1
Serine/threonine-protein kinase VRK1
CHEMBL1293199
 Ki 7.25 7.25 56.1 1
H9
CHEMBL614806
 IC50 7.22 7.22 60.2 1
KARPAS-45
CHEMBL2366305
 IC50 6.78 6.78 165.2 1
NCI-H720
CHEMBL2366105
 IC50 6.76 6.76 171.9 1
Casein kinase I isoform alpha
CHEMBL2793
 IC50 6.35 6.35 450.0 1
CTV-1
CHEMBL2366360
 IC50 6.32 6.32 478.7 1
DU-4475
CHEMBL2366246
 IC50 6.3 6.3 504.2 1
A 172
CHEMBL614512
 IC50 6.29 6.29 517.0 1
EW-18
CHEMBL2366097
 IC50 6.21 6.21 622.1 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 Kd 6.21 5.955 620.0 2
KU812 cell line
CHEMBL613997
 IC50 6.2 6.2 626.2 1
KP-N-YS
CHEMBL2366065
 IC50 6.17 6.17 682.2 1
SBC-1
CHEMBL2366327
 IC50 6.16 6.16 695.2 1
ECC10
CHEMBL2366117
 IC50 6.15 6.15 700.9 1
GAMG
CHEMBL1075447
 IC50 6.13 6.13 747.2 1
NCI-H209
CHEMBL2366365
 IC50 6.12 6.12 768.2 1
MC-IXC
CHEMBL1075495
 IC50 6.1 6.1 795.9 1
HSC-3
CHEMBL612279
 IC50 6.09 6.09 817.7 1
IST-SL1
CHEMBL2366104
 IC50 6.07 6.07 845.7 1
LU-139
CHEMBL2366248
 IC50 6.07 6.07 849.6 1
ML-2
CHEMBL614356
 IC50 6.07 6.07 855.8 1
CAL-62
CHEMBL1075413
 IC50 6.05 6.05 881.5 1
KY821
CHEMBL2366190
 IC50 6.05 6.05 888.1 1
HL-60
CHEMBL383
 IC50 6.05 6.05 883.6 1
ES7
CHEMBL2366297
 IC50 6.04 6.04 916.1 1
MV4-11
CHEMBL613835
 IC50 6.01 6.01 979.0 1
Daoy
CHEMBL612519
 IC50 6.0 6.0 987.7 1
EOL1
CHEMBL614489
 IC50 5.99 5.99 1018.8 1
TGW
CHEMBL1075600
 IC50 5.98 5.98 1051.2 1
KOSC-2
CHEMBL1075481
 IC50 5.95 5.95 1133.8 1
LAMA-84
CHEMBL2366090
 IC50 5.95 5.95 1127.9 1
A549
CHEMBL392
 IC50 5.88 5.88 1309.5 1
CTB-1
CHEMBL2366344
 IC50 5.84 5.84 1446.8 1
LoVo
CHEMBL614721
 IC50 5.83 5.83 1467.5 1
NCI-H292
CHEMBL614733
 IC50 5.83 5.83 1460.7 1
BFTC-905
CHEMBL1075396
 IC50 5.81 5.81 1563.3 1
KE-37
CHEMBL2366287
 IC50 5.8 5.8 1594.8 1
BE-13
CHEMBL2366303
 IC50 5.8 5.8 1587.1 1
HN
CHEMBL1075465
 IC50 5.79 5.79 1613.7 1
A3-KAW
CHEMBL2366273
 IC50 5.79 5.79 1628.3 1
Ramos-2G6-4C10
CHEMBL2366170
 IC50 5.77 5.77 1704.4 1

Pharmacokinetic Data

Parameter Value Units Species
CL 44.6 mL.min-1.g-1 Homo sapiens
CL 69.9 mL.min-1.g-1 Mus musculus
T1/2 0.5367 hr Homo sapiens
T1/2 0.3383 hr Mus musculus
T1/2 0.1283 hr Homo sapiens
T1/2 0.14 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Ribosomal protein S6 kinase alpha-1 IC50 = 3.0 nM 8.52 Inhibition of RSK1 (unknown origin) 31982240
Ribosomal protein S6 kinase alpha-3 IC50 = 4.0 nM 8.4 Inhibition of RSK2 (unknown origin) 31982240
Unchecked IC50 = 10.0 nM 8.0 Inhibition of recombinant N-terminal RSK (unknown origin) expressed in Sf21 cell... 36898330
Ribosomal protein S6 kinase alpha-1 IC50 = 10.0 nM 8.0 Inhibition of N-terminal His6-tagged rat RSK1 expressed in baculovirus infected ... 38780468
Ribosomal protein S6 kinase alpha-3 IC50 = 10.0 nM 8.0 Inhibition of N-terminal His6-tagged human RSK2 expressed in baculovirus infecte... 38780468
Ribosomal protein S6 kinase alpha-2 IC50 = 10.0 nM 8.0 Inhibition of RSK3 (14 to 462 residues) (unknown origin) using KEAKEKRQEQIAKRRRL... 38780468
Ribosomal protein S6 kinase alpha-6 IC50 = 10.0 nM 8.0 Inhibition of RSK4 (14 to 702 residues) (unknown origin) using KEAKEKRQEQIAKRRRL... 38780468
Ribosomal protein S6 kinase alpha-6 IC50 = 11.5 nM 7.94 Inhibition of RSK4 (unknown origin) incubated for 40 mins in presence of ATP and... 34496560
Ribosomal protein S6 kinase alpha-2 IC50 = 13.0 nM 7.89 Inhibition of RSK3 (unknown origin) 31982240
Ribosomal protein S6 kinase alpha-6 IC50 = 15.0 nM 7.82 Inhibition of RSK4 (unknown origin) using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK a sub... 31982240
Ribosomal protein S6 kinase alpha-6 IC50 = 15.0 nM 7.82 Inhibition of RSK4 (unknown origin) 34496560
Ribosomal protein S6 kinase alpha-6 IC50 = 15.0 nM 7.82 Inhibition of RSK4 (unknown origin) 27559828
Ribosomal protein S6 kinase alpha-2 IC50 = 18.0 nM 7.75 Inhibition of RSK3 (unknown origin) 27559828
Ribosomal protein S6 kinase alpha-2 IC50 = 18.0 nM 7.75 Inhibition of RSK3 (unknown origin) using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK a sub... 31982240
Ribosomal protein S6 kinase alpha-2 IC50 = 18.0 nM 7.75 Inhibition of RSK3 (unknown origin) 34496560
Ribosomal protein S6 kinase alpha-2 IC50 = 18.0 nM 7.75 Inhibition of human RSK3 27559828
Ribosomal protein S6 kinase alpha-3 IC50 = 22.6 nM 7.65 Inhibition of RSK2 (unknown origin) using Ulight-rpS6 as substrate incubated for... 34034149
Ribosomal protein S6 kinase alpha-3 IC50 = 24.0 nM 7.62 Inhibition of His6-tagged human RSK2 using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK-pept... 34496560
Ribosomal protein S6 kinase alpha-3 IC50 = 24.0 nM 7.62 Inhibition of RSK2 (unknown origin) using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK a sub... 31982240
Ribosomal protein S6 kinase alpha-3 IC50 = 24.0 nM 7.62 Inhibition of RSK2 (unknown origin) 27559828

Literature References

PubMed DOI Target Context # Activities
38780468 10.1021/acs.jmedchem.3c02250 ADMET 8
31982240 10.1016/j.bmc.2019.115303 MOLM-13 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
31982240 10.1016/j.bmc.2019.115303 Ribosomal protein S6 kinase alpha-3 4
34034149 10.1016/j.bmc.2021.116220 Ribosomal protein S6 kinase alpha-3 3
34496560 10.1021/acs.jmedchem.1c00969 TE-10 3
38780468 10.1021/acs.jmedchem.3c02250 Serine/threonine-protein kinase VRK1 2
31531195 10.1021/acsmedchemlett.9b00082 Serine/threonine-protein kinase VRK1 2
32329617 10.1021/acs.jmedchem.0c00192 Tyrosine-protein kinase JAK2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
31982240 10.1016/j.bmc.2019.115303 Ribosomal protein S6 kinase alpha-1 2
31982240 10.1016/j.bmc.2019.115303 Ribosomal protein S6 kinase alpha-2 2
27559828 10.1021/acs.jmedchem.6b00438 Ribosomal protein S6 kinase alpha-2 2
38780468 10.1021/acs.jmedchem.3c02250 Serine/threonine-protein kinase VRK2 2
17850214 10.1042/bj20070797 Unchecked 2
27559828 10.1021/acs.jmedchem.6b00438 Ribosomal protein S6 kinase alpha-1 2
34496560 10.1021/acs.jmedchem.1c00969 Ribosomal protein S6 kinase alpha-6 2
38780468 10.1021/acs.jmedchem.3c02250 No relevant target 2
17850214 10.1042/bj20070797 Serine/threonine-protein kinase pim-3 1

Data from ChEMBL 36 via Core Engine