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Compound Detail

CHEMBL3955519

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CCOC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NC(C4CC4)C4CC4)nc(Cl)nc31)[C@H](O)[C@@H]2O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3955519
Phase Preclinical
Structure Type MOL
InChI Key IRHYVDDJDDMRKD-QNEDUEMWSA-N
7
Targets
14
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

447.9
MW (Da)
1.93
ALogP
9
HBA
3
HBD
122.4
PSA (Ų)
0.43
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H26ClN5O4
MW 447.92
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness 0.12

Activity Summary

Ki 14 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 8.74 8.1267 1.8 3
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 8.41 7.7333 3.9 3
Adenosine receptor A3
CHEMBL256
 Ki 6.63 6.63 236.0 1
Transmembrane domain-containing protein TMIGD3
CHEMBL3712907
 Ki 6.63 6.63 236.0 1
Adenosine receptor A1
CHEMBL226
 Ki 6.44 6.44 360.0 2
Adenosine receptor A2a
CHEMBL251
 Ki 5.8 5.8 1570.0 2
Translocator protein
CHEMBL5742
 Ki 5.68 5.64 2100.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2B Ki = 1.8 nM 8.74 Antagonist activity at human 5-HT2BR expressed in Flp-In HEK cells assessed as i... 27933810
5-hydroxytryptamine receptor 2C Ki = 3.9 nM 8.41 Antagonist activity at human 5-HT2CR expressed in Flp-In HEK cells assessed as i... 27933810
5-hydroxytryptamine receptor 2B Ki = 15.0 nM 7.82 Displacement of [3H]lysergic from human 5-HT2BR expressed in HEK cell membranes ... 27933810
5-hydroxytryptamine receptor 2B Ki = 15.0 nM 7.82 Inhibition of 5HT2B (unknown origin) 30605331
5-hydroxytryptamine receptor 2C Ki = 30.0 nM 7.52 Displacement of [3H]mesulergine from human 5-HT2CR expressed in Flp-In HEK cell ... 27933810
5-hydroxytryptamine receptor 2C Ki = 54.0 nM 7.27 Inhibition of 5HT2C (unknown origin) 30605331
Transmembrane domain-containing protein TMIGD3 Ki = 236.0 nM 6.63 Displacement of [125l]N 6-(4-amino-3-iodobenzyl)adenosine-5'-N-methyluronamide f... 27933810
Adenosine receptor A3 Ki = 236.0 nM 6.63 Displacement of [125I]N6-(4-amino-3-iodobenzyl)adenosine-5-N-methyluronamide fro... 30605331
Adenosine receptor A1 Ki = 360.0 nM 6.44 Displacement of [3H]N6-phenylisopropyladenosine from recombinant human A1AR expr... 27933810
Adenosine receptor A1 Ki = 360.0 nM 6.44 Displacement of [3H]N6-R-phenylisopropyladenosine from human A1A adenosine recep... 30605331
Adenosine receptor A2a Ki = 1570.0 nM 5.8 Displacement of [3 H]2-[p-(2-carboxyethyl)phenyl-ethylamino]-5'-N-ethylcarboxami... 27933810
Adenosine receptor A2a Ki = 1570.0 nM 5.8 Displacement of [3H]2-[p-(2-carboxyethyl)phenylethylamino]-5-N-ethylcarboxamidoa... 30605331
Translocator protein Ki = 2100.0 nM 5.68 Inhibition of TSPO (unknown origin) 27933810
Translocator protein Ki = 2500.0 nM 5.6 Inhibition of TSPO (unknown origin) 30605331

Literature References

PubMed DOI Target Context # Activities
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 2B 5
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 2C 4
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 2A 4
33031923 10.1016/j.bmcl.2020.127599 Enterovirus A71 2
33031923 10.1016/j.bmcl.2020.127599 Vero 76 2
33031923 10.1016/j.bmcl.2020.127599 Unchecked 2
27933810 10.1021/acs.jmedchem.6b01183 Adenosine receptor A1 2
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 7 1
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 3A 1
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 6 1
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 4 1
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 1E 1
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 1D 1
27933810 10.1021/acs.jmedchem.6b01183 Adenosine receptor A2a 1
27933810 10.1021/acs.jmedchem.6b01183 Transmembrane domain-containing protein TMIGD3 1
27933810 10.1021/acs.jmedchem.6b01183 Adenosine receptor A3 1
27933810 10.1021/acs.jmedchem.6b01183 Translocator protein 1
30605331 10.1021/acs.jmedchem.8b01662 Adenosine receptor A1 1
30605331 10.1021/acs.jmedchem.8b01662 Adenosine receptor A2a 1
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 1B 1

Data from ChEMBL 36 via Core Engine