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Compound Detail

CHEMBL2012686

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O[C@@H]1[C@H](O)[C@@H]2C[C@@H]2[C@H]1n1cnc2c(NC(C3CC3)C3CC3)nc(Cl)nc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2012686
Phase Preclinical
Structure Type MOL
InChI Key XJBGUZYJXHUHPS-HLXQIYJLSA-N

Known Names

MRS-5474
11
Targets
28
Activities
2
Assay Types
5
PK Parameters
20
Publications
1
Known Names

Molecular Properties

375.9
MW (Da)
1.99
ALogP
7
HBA
3
HBD
96.1
PSA (Ų)
0.69
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H22ClN5O2
MW 375.86
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.06

Activity Summary

Ki 22 meas. best 9.1
EC50 6 meas. best 8.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL318
 Ki 9.1 9.1 0.8 1
Adenosine receptor A1
CHEMBL3688
 Ki 8.28 8.28 5.2 1
Adenosine receptor A1
CHEMBL318
 EC50 8.18 8.18 6.7 1
Adenosine receptor A1
CHEMBL226
 EC50 7.39 7.39 40.7 1
Adenosine receptor A1
CHEMBL226
 Ki 7.32 7.32 47.9 5
Adenosine receptor A3
CHEMBL256
 Ki 6.33 6.33 470.0 4
Transmembrane domain-containing protein TMIGD3
CHEMBL3712907
 Ki 6.33 6.33 470.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.19 6.18 641.0 2
Adenosine receptor A3
CHEMBL1075269
 Ki 5.97 5.97 1060.0 1
Adenosine receptor A3
CHEMBL256
 EC50 5.86 5.86 1370.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 5.73 5.73 1850.0 2
Enterovirus A71
CHEMBL612436
 EC50 5.47 5.455 3400.0 2
Adenosine receptor A2a
CHEMBL251
 Ki 5.4 5.4 3950.0 5
enterovirus D68
CHEMBL613204
 EC50 5.03 5.03 9300.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 98.0 % Mus musculus
F 124.0 % Mus musculus
F 24.0 % Macaca fascicularis
T1/2 2.5 hr Mus musculus
T1/2 5.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 Ki = 0.8 nM 9.1 Displacement of [3H]R-PIA from rat forebrain adenosine receptor-1 21858244
Adenosine receptor A1 Ki = 5.2 nM 8.28 Displacement of [3H]N6-R-phenylisopropyladenosine from mouse A1A adenosine recep... 30605331
Adenosine receptor A1 EC50 = 6.65 nM 8.18 Agonist activity at rat A1A adenosine receptor expressed in CHO-K1 cell membrane... 30605331
Adenosine receptor A1 EC50 = 40.7 nM 7.39 Agonist activity at human recombinant adenosine receptor-1 expressed in CHO cell... 21858244
Adenosine receptor A1 Ki = 47.9 nM 7.32 Displacement of [3H]R-PIA from human recombinant adenosine receptor-1 expressed ... 21858244
Adenosine receptor A1 Ki = 47.9 nM 7.32 Displacement of [3H]R-PIA from human A1 adenosine receptor expressed in CHO cell... 22921089
Adenosine receptor A1 Ki = 48.0 nM 7.32 Displacement of [3H]N6-phenylisopropyladenosine from recombinant human A1AR expr... 27933810
Adenosine receptor A1 Ki = 47.9 nM 7.32 Displacement of [3H]DPCPX from recombinant human A1 receptor expressed in CHO ce... 30568760
Adenosine receptor A1 Ki = 47.9 nM 7.32 Displacement of [3H]N6-R-phenylisopropyladenosine from human A1A adenosine recep... 30605331
Adenosine receptor A3 Ki = 470.0 nM 6.33 Displacement of [125I]I-AB-MECA from human A3 adenosine receptor expressed in CH... 22921089
Adenosine receptor A3 Ki = 470.0 nM 6.33 Displacement of [125I]N6-(4-amino-3-iodobenzyl)adenosine-5-N-methyluronamide fro... 30605331
Adenosine receptor A3 Ki = 470.0 nM 6.33 Displacement of [125I]I-AB-MECA from recombinant human adenosine A3 receptor exp... 30568760
Transmembrane domain-containing protein TMIGD3 Ki = 470.0 nM 6.33 Displacement of [125l]N 6-(4-amino-3-iodobenzyl)adenosine-5'-N-methyluronamide f... 27933810
Adenosine receptor A3 Ki = 470.0 nM 6.33 Displacement of [125I]AB-MECA from human recombinant adenosine receptor-3 expres... 21858244
5-hydroxytryptamine receptor 2B Ki = 641.0 nM 6.19 Inhibition of 5HT2B (unknown origin) 30605331
5-hydroxytryptamine receptor 2B Ki = 675.0 nM 6.17 Displacement of [3H]lysergic from human 5-HT2BR expressed in HEK cell membranes ... 27933810
Adenosine receptor A3 Ki = 1060.0 nM 5.97 Displacement of [125I]N6-(4-amino-3-iodobenzyl)adenosine-5-N-methyluronamide fro... 30605331
Adenosine receptor A3 EC50 = 1370.0 nM 5.86 Agonist activity at human A3A adenosine receptor expressed in HEK cell membranes... 30605331
5-hydroxytryptamine receptor 2C Ki = 1860.0 nM 5.73 Displacement of [3H]mesulergine from human 5-HT2CR expressed in Flp-In HEK cell ... 27933810
5-hydroxytryptamine receptor 2C Ki = 1850.0 nM 5.73 Inhibition of 5HT2C (unknown origin) 30605331

Literature References

PubMed DOI Target Context # Activities
30605331 10.1021/acs.jmedchem.8b01662 ADMET 13
22921089 10.1021/jm300965a Mus musculus 8
30605331 10.1021/acs.jmedchem.8b01662 Adenosine receptor A1 4
30605331 10.1021/acs.jmedchem.8b01662 Adenosine receptor A3 4
21858244 10.1021/ml200114q Adenosine receptor A1 4
33031923 10.1016/j.bmcl.2020.127599 Unchecked 4
33031923 10.1016/j.bmcl.2020.127599 enterovirus D68 2
27933810 10.1021/acs.jmedchem.6b01183 Adenosine receptor A2a 2
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 2C 2
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 2B 2
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 2A 2
30605331 10.1021/acs.jmedchem.8b01662 No relevant target 2
30605331 10.1021/acs.jmedchem.8b01662 Adenosine receptor A2a 2
33031923 10.1016/j.bmcl.2020.127599 Enterovirus A71 2
33031923 10.1016/j.bmcl.2020.127599 Vero 76 2
22921089 10.1021/jm300965a Adenosine receptor A1 2
30605331 10.1021/acs.jmedchem.8b01662 Mus musculus 2
21858244 10.1021/ml200114q Unchecked 2
33031923 10.1016/j.bmcl.2020.127599 RD 2
33031923 10.1016/j.bmcl.2020.127599 Respiratory syncytial virus 1

Data from ChEMBL 36 via Core Engine