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Compound Detail

CHEMBL188343

REVERSINE
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c1nc2c(NC3CCCCC3)nc(Nc3ccc(N4CCOCC4)cc3)nc2[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL188343
Name REVERSINE
Phase Preclinical
Structure Type MOL
InChI Key ZFLJHSQHILSNCM-UHFFFAOYSA-N
15
Targets
40
Activities
2
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

393.5
MW (Da)
3.68
ALogP
7
HBA
3
HBD
91.0
PSA (Ų)
0.61
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H27N7O
MW 393.50
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.44

Activity Summary

IC50 39 meas. best 8.55
Ki 1 meas. best 6.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dual specificity protein kinase TTK
CHEMBL3983
 IC50 8.55 8.45 2.8 3
Dual specificity mitogen-activated protein kinase kinase 1
CHEMBL5860
 IC50 8.1 8.1 8.0 1
Unchecked
CHEMBL612545
 IC50 8.0 6.698 10.0 5
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 7.22 7.07 60.0 4
HCT-116
CHEMBL394
 IC50 7.16 6.85 70.0 4
Aurora kinase B
CHEMBL2185
 IC50 7.12 6.81 75.0 3
Aurora kinase A
CHEMBL4722
 IC50 6.96 6.68 110.0 2
HeLa
CHEMBL399
 IC50 6.94 6.6875 116.0 4
DLD-1
CHEMBL614285
 IC50 6.92 6.895 120.3 2
U2OS
CHEMBL615023
 IC50 6.81 6.81 154.1 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 6.52 5.925 300.0 2
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 6.46 6.46 350.0 2
Aurora kinase C
CHEMBL3935
 IC50 6.4 6.4 400.0 1
Adenosine receptor A3
CHEMBL256
 Ki 6.18 6.18 660.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 6.17 5.968 680.0 5

Pharmacokinetic Data

Parameter Value Units Species
AUC 786.4 hr.ng/L Mus musculus
AUC 30.1 hr.ng/L Mus musculus
Cmax 0.1944 nM Mus musculus
Cmax 0.04651 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dual specificity protein kinase TTK IC50 = 2.8 nM 8.55 Inhibition of human TTK-mediated MAD1/MAD2 complex phosphorylation after 1 hr by... 25763473
Dual specificity protein kinase TTK IC50 = 4.0 nM 8.4 Inhibition of Mps1 22632936
Dual specificity protein kinase TTK IC50 = 4.0 nM 8.4 Inhibition of MPS1 (unknown origin) using MAD1-MAD2 complex as substrate incubat... 38095579
Dual specificity mitogen-activated protein kinase kinase 1 IC50 = 8.0 nM 8.1 Inhibition of MEK1 in mouse C2C12 by ERK2 phosphorylation assay 17566101
Unchecked IC50 = 10.0 nM 8.0 Inhibition of ATPase activity of myosin 2 in mouse C2C12 myoblast assessed as re... 17566101
Non-receptor tyrosine-protein kinase TYK2 IC50 = 60.0 nM 7.22 Inhibition of human recombinant C-terminal Histidine tagged TYK2 JH2 (564 to 876... 37578217
Non-receptor tyrosine-protein kinase TYK2 IC50 = 60.0 nM 7.22 Inhibition of human recombinant TYK2 JH2 37578217
HCT-116 IC50 = 70.0 nM 7.16 Inhibition of colony formation in human HCT-116 cells harboring Mps1 C604Y mutan... 26364596
Aurora kinase B IC50 = 75.0 nM 7.12 Inhibition of Aur B 22632936
HCT-116 IC50 = 78.9 nM 7.1 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 26364596
Aurora kinase B IC50 = 98.5 nM 7.01 Inhibition of GST-fused AURORA B (1 to 344 residues) expressed in Escherichia co... 38095579
Aurora kinase A IC50 = 110.0 nM 6.96 Inhibition of Aur A 22632936
HeLa IC50 = 116.0 nM 6.94 Inhibition of colony formation in human HeLa cells harboring Mps1 C604Y mutant a... 26364596
Non-receptor tyrosine-protein kinase TYK2 IC50 = 120.0 nM 6.92 Inhibition of human recombinant C-terminal Histidine tagged TYK2 JH1 (886 to 118... 37578217
Non-receptor tyrosine-protein kinase TYK2 IC50 = 120.0 nM 6.92 Inhibition of human recombinant TYK2 JH1 37578217
DLD-1 IC50 = 120.3 nM 6.92 Antiproliferative activity against human DLD-1 cells assessed as reduction in ce... 26364596
HeLa IC50 = 125.0 nM 6.9 Inhibition of colony formation in human HeLa cells harboring Mps1 C604F mutant a... 26364596
DLD-1 IC50 = 136.0 nM 6.87 Inhibition of colony formation in human DLD-1 cells assessed as cell survival in... 26364596
HCT-116 IC50 = 138.0 nM 6.86 Inhibition of colony formation in human HCT-116 cells assessed as cell survival ... 26364596
Unchecked IC50 = 150.0 nM 6.82 Inhibition of JAK1 JH2 domain (unknown origin) 37578217

Literature References

PubMed DOI Target Context # Activities
17566101 10.1073/pnas.0704360104 C2C12 35
17566101 10.1073/pnas.0704360104 Unchecked 6
37578217 10.1021/acs.jmedchem.3c00926 Tyrosine-protein kinase JAK2 5
37578217 10.1021/acs.jmedchem.3c00926 Unchecked 4
26364596 10.1038/onc.2015.319 HeLa 4
31121430 10.1016/j.ejmech.2019.04.047 ADMET 4
26364596 10.1038/onc.2015.319 HCT-116 4
37578217 10.1021/acs.jmedchem.3c00926 Non-receptor tyrosine-protein kinase TYK2 4
26364596 10.1038/onc.2015.319 DLD-1 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
16033270 10.1021/jm050221l Adenosine receptor A3 2
38095579 10.1021/acs.jmedchem.3c00963 Dual specificity protein kinase TTK 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37578217 10.1021/acs.jmedchem.3c00926 Tyrosine-protein kinase JAK1 2
31121430 10.1016/j.ejmech.2019.04.047 HCT-116 2
37578217 10.1021/acs.jmedchem.3c00926 Tyrosine-protein kinase JAK3 2
25763473 10.1021/jm501740a Dual specificity protein kinase TTK 1
22632936 10.1016/j.bmcl.2012.04.131 Serine/threonine-protein kinase PLK1 1
17566101 10.1073/pnas.0704360104 Dual specificity mitogen-activated protein kinase kinase 1 1
16033270 10.1021/jm050221l Adenosine receptor A2a 1

Data from ChEMBL 36 via Core Engine