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Compound Detail

CHEMBL2171452

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COc1ccc(C2=NN(C3CCCCCC3)C(=O)C2(C)C)cc1OCCCCOc1ccc(-c2nn[nH]n2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2171452
Phase Preclinical
Structure Type MOL
InChI Key JPXAIORZGBCHIB-UHFFFAOYSA-N
12
Targets
19
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

546.7
MW (Da)
5.41
ALogP
8
HBA
1
HBD
114.8
PSA (Ų)
0.25
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H38N6O4
MW 546.67
Aromatic Rings 3
Heavy Atoms 40
NP-Likeness -0.55

Activity Summary

IC50 15 meas. best 8.92
Ki 4 meas. best 5.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 8.92 8.92 1.2 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 8.68 8.68 2.1 1
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 8.34 8.34 4.6 1
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 8.0 8.0 10.0 1
Class 1 phosphodiesterase PDEB1
CHEMBL2010636
 IC50 7.31 7.285 49.0 2
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 7.22 7.22 60.0 1
Unchecked
CHEMBL612545
 IC50 7.14 7.14 72.0 1
Class I phosphodiesterase PDEB1
CHEMBL2169733
 IC50 6.89 6.89 130.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.28 5.9475 520.0 4
Trypanosoma brucei
CHEMBL612849
 IC50 6.1 6.1 790.0 1
DNA (cytosine-5)-methyltransferase 3A
CHEMBL1992
 Ki 5.43 5.075 3700.0 4
Trypanosoma cruzi
CHEMBL368
 IC50 5.12 5.12 7600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.2 nM 8.92 Inhibition of human PDE4D3 expressed in Sf21 insect cells assessed as reduction ... 22963052
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 2.1 nM 8.68 Inhibition of human PDE4A1 expressed in Sf21 insect cells assessed as reduction ... 22963052
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 4.6 nM 8.34 Inhibition of human PDE4B1 expressed in Sf21 insect cells assessed as reduction ... 22963052
3',5'-cyclic-AMP phosphodiesterase 4C IC50 = 10.0 nM 8.0 Inhibition of human PDE4C1 expressed in Sf21 insect cells assessed as reduction ... 22963052
Class 1 phosphodiesterase PDEB1 IC50 = 49.0 nM 7.31 Inhibition of Trypanosoma brucei recombinant TbrPDEB1 expressed in Sf21 insect c... 22963052
Class 1 phosphodiesterase PDEB1 IC50 = 55.0 nM 7.26 Inhibition of Trypanosoma brucei His-tagged catalytic domains of TbrPDEB1 expres... 22963052
Trypanosoma brucei rhodesiense IC50 = 60.0 nM 7.22 Antitrypanosomal activity against trypomastigotes of Trypanosoma brucei rhodesie... 22963052
Unchecked IC50 = 72.0 nM 7.14 Inhibition of Trypanosoma brucei recombinant TbrPDEB2 expressed in yeast assesse... 22963052
Class I phosphodiesterase PDEB1 IC50 = 130.0 nM 6.89 Inhibition of Leishmania major recombinant PDEB1 expressed in Sf21 insect cells ... 22963052
Trypanosoma brucei brucei IC50 = 520.0 nM 6.28 Antitrypanosomal activity against trypomastigotes of Trypanosoma brucei brucei S... 22963052
Trypanosoma brucei IC50 = 790.0 nM 6.1 AntiTrypanosoma brucei activity T. b. brucei IC50 (uM) -
Trypanosoma brucei brucei IC50 = 790.0 nM 6.1 Antitrypanosomal activity against Trypanosoma brucei brucei by pathogen box scre... 30647879
Trypanosoma brucei brucei IC50 = 1700.0 nM 5.77 Antitrypanosomal activity against Trypanosoma brucei brucei 427 bloodstream form... 30647879
Trypanosoma brucei brucei IC50 = 2300.0 nM 5.64 Antitrypanosomal activity against Trypanosoma brucei brucei 427 bloodstream form... 30647879
DNA (cytosine-5)-methyltransferase 3A Ki = 3700.0 nM 5.43 Mixed type inhibition of human DNMT3A using AdoMet as substrate 33705897
DNA (cytosine-5)-methyltransferase 3A Ki = 5030.0 nM 5.3 Binding affinity to human DNMT3A catalytic domain assessed as inhibition of enzy... 33705897
Trypanosoma cruzi IC50 = 7600.0 nM 5.12 Antitrypanosomal activity against trypomastigotes of Trypanosoma cruzi after 72 ... 22963052
DNA (cytosine-5)-methyltransferase 3A Ki = 12640.0 nM 4.9 Mixed type inhibition of human DNMT3A using poly dl-dC as substrate 33705897
DNA (cytosine-5)-methyltransferase 3A Ki = 21570.0 nM 4.67 Binding affinity to human DNMT3A catalytic domain assessed as inhibition of enzy... 33705897

Literature References

PubMed DOI Target Context # Activities
35866897 10.1021/acs.jmedchem.2c00725 Unchecked 7
33705897 10.1016/j.bmcl.2021.127908 DNA (cytosine-5)-methyltransferase 3A 5
22963052 10.1021/jm301059b Trypanosoma brucei brucei 5
30647879 10.1039/C8MD00319J Trypanosoma brucei brucei 4
22963052 10.1021/jm301059b ADMET 3
35866897 10.1021/acs.jmedchem.2c00725 DNA (cytosine-5)-methyltransferase 3A 3
22963052 10.1021/jm301059b Class 1 phosphodiesterase PDEB1 2
35866897 10.1021/acs.jmedchem.2c00725 DNMT3A2/3L complex 2
22963052 10.1021/jm301059b 3',5'-cyclic-AMP phosphodiesterase 4A 1
22963052 10.1021/jm301059b Class I phosphodiesterase PDEB1 1
22963052 10.1021/jm301059b 3',5'-cyclic-AMP phosphodiesterase 4B 1
22963052 10.1021/jm301059b Unchecked 1
22963052 10.1021/jm301059b MRC5 1
- 10.6019/CHEMBL3832761 Trypanosoma brucei 1
- 10.6019/CHEMBL3987221 Ferrochelatase, mitochondrial 1
22963052 10.1021/jm301059b 3',5'-cyclic-AMP phosphodiesterase 4D 1
22963052 10.1021/jm301059b Trypanosoma brucei rhodesiense 1
30647879 10.1039/C8MD00319J HeLa 1
- 10.6019/CHEMBL4513101 Naegleria gruberi 1
22963052 10.1021/jm301059b Trypanosoma cruzi 1

Data from ChEMBL 36 via Core Engine