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Compound Detail

CHEMBL4571380

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COc1cc(CCNc2nc(C#Cc3ccccc3)nc3c2ncn3[C@H]2[C@H](O)[C@H](O)[C@@H]3C[C@@H]32)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4571380
Phase Preclinical
Structure Type MOL
InChI Key VNPDINLPSRFSFN-OMUDAWCKSA-N
10
Targets
17
Activities
3
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

497.6
MW (Da)
2.51
ALogP
9
HBA
4
HBD
125.5
PSA (Ų)
0.30
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H27N5O4
MW 497.56
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness 0.12

Activity Summary

Ki 9 meas. best 7.96
IC50 7 meas. best 5.65
EC50 1 meas. best 6.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A3
CHEMBL256
 Ki 7.96 7.96 10.9 2
Adenosine receptor A3
CHEMBL1075269
 Ki 7.75 7.75 17.8 2
Adenosine receptor A3
CHEMBL256
 EC50 6.8 6.8 158.0 1
Adenosine receptor A1
CHEMBL3688
 Ki 6.23 6.23 590.0 2
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 5.7 5.7 1980.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.65 5.65 2230.0 2
Translocator protein
CHEMBL5742
 Ki 5.65 5.65 2220.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.54 5.54 2890.0 2
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 5.45 5.45 3570.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.27 5.27 5390.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.84 4.84 14400.0 2

Pharmacokinetic Data

Parameter Value Units Species
F 1.5 % Rattus norvegicus
F 3.5 % Rattus norvegicus
F 3.49 % Rattus norvegicus
T1/2 0.457 hr Rattus norvegicus
T1/2 0.49 hr Rattus norvegicus
T1/2 0.274 hr Rattus norvegicus
T1/2 0.132 hr Mus musculus
T1/2 0.2617 hr Rattus norvegicus
T1/2 0.2717 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A3 Ki = 10.9 nM 7.96 Displacement of [125I]I-AB-MECA from recombinant human A3AR expressed in HEK293 ... 32271569
Adenosine receptor A3 Ki = 10.9 nM 7.96 Displacement of [125I] N6-(4-amino-3-iodobenzyl)adenosine-5'-N-methyluronamide f... 34844790
Adenosine receptor A3 Ki = 17.8 nM 7.75 Displacement of [125I] N6-4-amino-3-iodobenzyl adenosine 5-N-methyluronamide fro... 34844790
Adenosine receptor A3 Ki = 17.8 nM 7.75 Displacement of [125I]I-AB-MECA from recombinant mouse A3AR expressed in HEK293 ... 32271569
Adenosine receptor A3 EC50 = 158.0 nM 6.8 Partial agonist activity at recombinant human A3AR expressed in HEK293 cells ass... 32271569
Adenosine receptor A1 Ki = 590.0 nM 6.23 Displacement of [3H] N6-R-phenylisopropyladenosine from mouse A1A receptor stabl... 34844790
Adenosine receptor A1 Ki = 590.0 nM 6.23 Displacement of [3H]R-PIA from recombinant mouse A1AR expressed in HEK293 cell m... 32271569
Sigma intracellular receptor 2 Ki = 1980.0 nM 5.7 Displacement of [3H]-DTG from sigma 2 receptor (unknown origin) measured after 9... 32271569
Cytochrome P450 3A4 IC50 = 2230.0 nM 5.65 Inhibition of CYP3A4 (unknown origin) using midazolam as substrate 32271569
Translocator protein Ki = 2220.0 nM 5.65 Inhibition of TSPO (unknown origin) 32271569
Cytochrome P450 3A4 IC50 = 2230.0 nM 5.65 Inhibition of CYP3A4 (unknown origin) 34844790
Cytochrome P450 1A2 IC50 = 2890.0 nM 5.54 Inhibition of CYP1A2 (unknown origin) 34844790
Cytochrome P450 1A2 IC50 = 2890.0 nM 5.54 Inhibition of CYP1A2 (unknown origin) 32271569
Sigma non-opioid intracellular receptor 1 Ki = 3570.0 nM 5.45 Displacement of [3H]-Pentazocine from sigma 1 receptor (unknown origin) measured... 32271569
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 5390.0 nM 5.27 Inhibition of human ERG 34844790
Cytochrome P450 2C9 IC50 = 14400.0 nM 4.84 Inhibition of CYP2C9 (unknown origin) 34844790
Cytochrome P450 2C9 IC50 = 14400.0 nM 4.84 Inhibition of CYP2C9 (unknown origin) using tolbutamide as substrate 32271569

Literature References

PubMed DOI Target Context # Activities
34844790 10.1016/j.ejmech.2021.113983 ADMET 12
32271569 10.1021/acs.jmedchem.0c00235 Adenosine receptor A3 7
32271569 10.1021/acs.jmedchem.0c00235 ADMET 7
32271569 10.1021/acs.jmedchem.0c00235 Mus musculus 4
34844790 10.1016/j.ejmech.2021.113983 Adenosine receptor A3 2
34844790 10.1016/j.ejmech.2021.113983 Adenosine receptor A1 2
32271569 10.1021/acs.jmedchem.0c00235 No relevant target 2
32271569 10.1021/acs.jmedchem.0c00235 Adenosine receptor A1 2
32271569 10.1021/acs.jmedchem.0c00235 Cytochrome P450 2C19 1
34844790 10.1016/j.ejmech.2021.113983 Cytochrome P450 3A4 1
34844790 10.1016/j.ejmech.2021.113983 Adenosine receptor A2a 1
34844790 10.1016/j.ejmech.2021.113983 Voltage-gated inwardly rectifying potassium channel KCNH2 1
34844790 10.1016/j.ejmech.2021.113983 No relevant target 1
32271569 10.1021/acs.jmedchem.0c00235 Cytochrome P450 3A4 1
32271569 10.1021/acs.jmedchem.0c00235 Cytochrome P450 2D6 1
32271569 10.1021/acs.jmedchem.0c00235 Cytochrome P450 2C9 1
32271569 10.1021/acs.jmedchem.0c00235 Cytochrome P450 1A2 1
32271569 10.1021/acs.jmedchem.0c00235 Translocator protein 1
32271569 10.1021/acs.jmedchem.0c00235 Sigma intracellular receptor 2 1
32271569 10.1021/acs.jmedchem.0c00235 Sigma non-opioid intracellular receptor 1 1

Data from ChEMBL 36 via Core Engine