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Compound Detail

CHEMBL1276317

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O=C1Nc2ccccc2/C1=C1/Nc2ccccc2/C1=N\OCC(O)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1276317
Phase Preclinical
Structure Type MOL
InChI Key ZWXBEUSAAVHLFW-DLOIKSOESA-N
11
Targets
19
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

351.4
MW (Da)
1.55
ALogP
6
HBA
4
HBD
103.2
PSA (Ų)
0.49
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H17N3O4
MW 351.36
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.33

Activity Summary

IC50 19 meas. best 7.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CDK6/cyclin D3
CHEMBL2111448
 IC50 7.12 7.12 75.0 1
MCF7
CHEMBL387
 IC50 7.0 7.0 100.0 2
Glycogen synthase kinase-3 beta
CHEMBL262
 IC50 6.96 6.96 110.0 1
Cyclin-dependent kinase 2/cyclin E1
CHEMBL1907605
 IC50 6.68 6.68 210.0 1
Unchecked
CHEMBL612545
 IC50 6.68 6.195 210.0 4
Proto-oncogene tyrosine-protein kinase Src
CHEMBL267
 IC50 6.37 6.2825 430.0 4
CDK2/Cyclin A2
CHEMBL3038469
 IC50 6.27 6.27 540.0 1
LXFL 529
CHEMBL614110
 IC50 6.05 6.05 900.0 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 6.02 6.02 950.0 1
Cyclin-dependent kinase 1/cyclin B1
CHEMBL1907602
 IC50 5.78 5.78 1650.0 1
HepG2
CHEMBL395
 IC50 5.68 5.615 2100.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CDK6/cyclin D3 IC50 = 75.0 nM 7.12 Inhibition of full length human N-terminal His6-tagged CDK6/N-terminal GST-tagge... 28557430
MCF7 IC50 = 100.0 nM 7.0 Antiproliferative activity against human MCF7 cells after 3 days by SRB assay 28557430
MCF7 IC50 = 100.0 nM 7.0 Antiproliferative activity against human MCF7 cells assessed as cell growth inhi... 34161865
Glycogen synthase kinase-3 beta IC50 = 110.0 nM 6.96 Inhibition of recombinant GSK3beta (unknown origin) after 10 mins in presence of... 28557430
Unchecked IC50 = 210.0 nM 6.68 Inhibition Cdk1/cyclin E 18077363
Cyclin-dependent kinase 2/cyclin E1 IC50 = 210.0 nM 6.68 Inhibition of full length human C-terminal His6-tagged CDK2/N-terminal GST-tagge... 28557430
Proto-oncogene tyrosine-protein kinase Src IC50 = 430.0 nM 6.37 Inhibition of Src 18077363
Proto-oncogene tyrosine-protein kinase Src IC50 = 430.0 nM 6.37 Inhibition of recombinant c-Src (unknown origin) 34161865
Proto-oncogene tyrosine-protein kinase Src IC50 = 430.0 nM 6.37 Inhibition of recombinant c-Src (unknown origin) incubated for 120 mins in prese... 35749986
Unchecked IC50 = 540.0 nM 6.27 Inhibition Cdk2/cyclin A 18077363
CDK2/Cyclin A2 IC50 = 540.0 nM 6.27 Inhibition of full length human C-terminal His6-tagged CDK2/N-terminal GST-tagge... 28557430
Unchecked IC50 = 900.0 nM 6.05 Antiproliferative activity against human LXFL 529L cells after 3 days by SRB ass... 28557430
LXFL 529 IC50 = 900.0 nM 6.05 Antiproliferative activity against human LXFL 529 cells assessed as cell growth ... 34161865
Proto-oncogene tyrosine-protein kinase Src IC50 = 950.0 nM 6.02 Inhibition of c-SRC in human MDA-MB-468 cells in presence of [gamma-32P]ATP and ... 34161865
Vascular endothelial growth factor receptor 2 IC50 = 950.0 nM 6.02 Inhibition of VEGFR2 (unknown origin) 34161865
Unchecked IC50 = 1650.0 nM 5.78 Inhibition of Cdk1/cyclin B 18077363
Cyclin-dependent kinase 1/cyclin B1 IC50 = 1650.0 nM 5.78 Inhibition of full length human C-terminal His6-tagged CDK1/N-terminal GST-tagge... 28557430
HepG2 IC50 = 2100.0 nM 5.68 Antiproliferative activity against human HepG2 cells assessed cell survival afte... 25765906
HepG2 IC50 = 2800.0 nM 5.55 Cytotoxicity against human HepG2 cells assessed cell death after 72 hrs by alama... 25765906

Literature References

PubMed DOI Target Context # Activities
25765906 10.1016/j.bmcl.2015.02.053 HepG2 5
18077363 10.1073/pnas.0708800104 Unchecked 3
28557430 10.1021/acs.jmedchem.7b00324 CDK2/Cyclin A2 2
34161865 10.1016/j.ejmech.2021.113652 Proto-oncogene tyrosine-protein kinase Src 2
34161865 10.1016/j.ejmech.2021.113652 CT26 2
28557430 10.1021/acs.jmedchem.7b00324 Glycogen synthase kinase-3 beta 2
28557430 10.1021/acs.jmedchem.7b00324 Cyclin-dependent kinase 2/cyclin E1 2
28557430 10.1021/acs.jmedchem.7b00324 Cyclin-dependent kinase 1/cyclin B1 2
18824607 10.1128/aac.00903-08 ADMET 2
28557430 10.1021/acs.jmedchem.7b00324 MCF7 1
28557430 10.1021/acs.jmedchem.7b00324 Unchecked 1
28557430 10.1021/acs.jmedchem.7b00324 No relevant target 1
25765906 10.1016/j.bmcl.2015.02.053 No relevant target 1
28557430 10.1021/acs.jmedchem.7b00324 CDK6/cyclin D3 1
28557430 10.1021/acs.jmedchem.7b00324 Cyclin-dependent kinase 4/cyclin D1 1
28557430 10.1021/acs.jmedchem.7b00324 Cyclin-dependent kinase 5/CDK5 activator 1 1
35749986 10.1016/j.ejmech.2022.114551 Proto-oncogene tyrosine-protein kinase Src 1
28557430 10.1021/acs.jmedchem.7b00324 Aurora kinase B 1
28557430 10.1021/acs.jmedchem.7b00324 Aurora kinase C 1
18824607 10.1128/aac.00903-08 Toxoplasma gondii 1

Data from ChEMBL 36 via Core Engine