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Compound Detail

CHEMBL2326941

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COc1ccc(C2=NN(C3CCCCCC3)C(=O)[C@@H]3CC=CC[C@H]23)cc1OCCCCOc1ccc(-c2nnn[nH]2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2326941
Phase Preclinical
Structure Type MOL
InChI Key DNDNLFXKQSTINI-WUFINQPMSA-N
14
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

584.7
MW (Da)
5.96
ALogP
8
HBA
1
HBD
114.8
PSA (Ų)
0.17
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 C33H40N6O4
MW 584.72
Aromatic Rings 3
Heavy Atoms 43
NP-Likeness -0.75

Activity Summary

IC50 22 meas. best 9.3
Ki 6 meas. best 9.2
EC50 1 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 9.3 9.25 0.5 2
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 9.2 9.2 0.6 1
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 Ki 9.2 9.2 0.6 1
Unchecked
CHEMBL612545
 IC50 8.52 7.3067 3.0 3
Class 1 phosphodiesterase PDEB1
CHEMBL2010636
 IC50 8.4 8.4 4.0 3
Class 1 phosphodiesterase PDEB1
CHEMBL2010636
 Ki 8.4 8.4 4.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 7.7 6.9733 20.0 3
Trypanosoma brucei brucei
CHEMBL612851
 EC50 7.7 7.7 19.9 1
Trypanosoma brucei
CHEMBL612849
 IC50 7.7 7.4 20.0 2
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
CHEMBL4409
 IC50 6.3 6.3 501.2 1
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A
CHEMBL2717
 IC50 5.7 5.7 1995.3 1
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 5.7 5.7 1995.3 1
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A
CHEMBL3012
 IC50 5.5 5.5 3162.3 1
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B
CHEMBL4408
 IC50 5.4 5.4 3981.1 1
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B
CHEMBL4425
 IC50 5.4 5.4 3981.1 1
cGMP-dependent 3',5'-cyclic phosphodiesterase
CHEMBL2652
 IC50 5.2 5.2 6309.6 1
DNA (cytosine-5)-methyltransferase 3A
CHEMBL1992
 Ki 5.04 4.9075 9160.0 4
DNA (cytosine-5)-methyltransferase 3A
CHEMBL1992
 IC50 4.85 4.85 14000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.5012 nM 9.3 Inhibition of full length human recombinant PDE4B2 using [3H]-cAMP as substrate ... 26935942
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.631 nM 9.2 Inhibition of full length human recombinant PDE4B1 using [3H]-cAMP as substrate ... 26935942
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.631 nM 9.2 Inhibition of full length human recombinant PDE4D3 using [3H]-cAMP as substrate ... 26935942
3',5'-cyclic-AMP phosphodiesterase 4B Ki = 0.631 nM 9.2 Inhibition of full length recombinant human PDE4B1 expressed in Sf21 insect cell... 29672041
Unchecked IC50 = 3.0 nM 8.52 Inhibition of Trypanosoma brucei PDEB2 using [3H]-cAMP as substrate after 15 min... 26935942
Unchecked IC50 = 3.162 nM 8.5 Inhibition of Trypanosoma brucei PDEB2 using [3H]-cAMP as substrate after 15 min... 26935942
Class 1 phosphodiesterase PDEB1 IC50 = 4.0 nM 8.4 Inhibition of Trypanosoma brucei full length PDEB1 expressed in insect SF21 cell... 23409953
Class 1 phosphodiesterase PDEB1 IC50 = 4.0 nM 8.4 Inhibition of recombinant Trypanosoma brucei PDEB1 using [3H]-cAMP as substrate ... 26935942
Class 1 phosphodiesterase PDEB1 IC50 = 3.981 nM 8.4 Inhibition of recombinant Trypanosoma brucei PDEB1 using [3H]-cAMP as substrate ... 26935942
Class 1 phosphodiesterase PDEB1 Ki = 3.981 nM 8.4 Inhibition of full length Trypanosoma brucei PDEB1 expressed in Sf21 insect cell... 29672041
Trypanosoma brucei IC50 = 20.0 nM 7.7 AntiTrypanosoma brucei activity T. b. brucei IC50 (uM) -
Trypanosoma brucei brucei IC50 = 20.0 nM 7.7 Antitrypanosomal activity against Trypanosoma brucei brucei by pathogen box scre... 30647879
Trypanosoma brucei brucei EC50 = 19.95 nM 7.7 Antitrypanosomal activity against suramin-sensitive Trypanosoma brucei brucei Sq... 26935942
Trypanosoma brucei IC50 = 80.0 nM 7.1 Antitrypanosomal activity against Trypanosoma brucei assessed as inhibition of p... 26935942
Trypanosoma brucei brucei IC50 = 120.0 nM 6.92 Antitrypanosomal activity against Trypanosoma brucei brucei 427 bloodstream form... 30647879
Trypanosoma brucei brucei IC50 = 500.0 nM 6.3 Antitrypanosomal activity against Trypanosoma brucei brucei 427 bloodstream form... 30647879
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 501.19 nM 6.3 Inhibition of full length human recombinant PDE10A using [3H]-cAMP as substrate ... 26935942
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A IC50 = 1995.26 nM 5.7 Inhibition of full length human recombinant PDE11A4 using [3H]-cAMP as substrate... 26935942
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 1995.26 nM 5.7 Inhibition of full length human recombinant PDE5A1 using [3H]-cGMP as substrate ... 26935942
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 3162.28 nM 5.5 Inhibition of full length human recombinant PDE7A1 using [3H]-cAMP as substrate ... 26935942

Literature References

PubMed DOI Target Context # Activities
35866897 10.1021/acs.jmedchem.2c00725 Unchecked 26
26935942 10.1016/j.bmc.2016.02.032 Unchecked 5
33705897 10.1016/j.bmcl.2021.127908 DNA (cytosine-5)-methyltransferase 3A 5
30647879 10.1039/C8MD00319J Trypanosoma brucei brucei 4
35866897 10.1021/acs.jmedchem.2c00725 DNMT3A2/3L complex 4
35866897 10.1021/acs.jmedchem.2c00725 DNA (cytosine-5)-methyltransferase 3A 4
26935942 10.1016/j.bmc.2016.02.032 Class 1 phosphodiesterase PDEB1 2
29672041 10.1021/acs.jmedchem.7b01670 Class 1 phosphodiesterase PDEB1 2
26935942 10.1016/j.bmc.2016.02.032 3',5'-cyclic-AMP phosphodiesterase 4B 2
26935942 10.1016/j.bmc.2016.02.032 cGMP-dependent 3',5'-cyclic phosphodiesterase 1
26935942 10.1016/j.bmc.2016.02.032 cGMP-specific 3',5'-cyclic phosphodiesterase 1
26935942 10.1016/j.bmc.2016.02.032 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
26935942 10.1016/j.bmc.2016.02.032 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B 1
26935942 10.1016/j.bmc.2016.02.032 High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A 1
26935942 10.1016/j.bmc.2016.02.032 cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A 1
38746896 10.1021/acsmedchemlett.3c00528 DNA (cytosine-5)-methyltransferase 3A 1
26935942 10.1016/j.bmc.2016.02.032 Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B 1
- 10.6019/CHEMBL3832761 Trypanosoma brucei 1
26935942 10.1016/j.bmc.2016.02.032 MRC5 1
26935942 10.1016/j.bmc.2016.02.032 Trypanosoma brucei brucei 1

Data from ChEMBL 36 via Core Engine