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Compound Detail

CHEMBL331382

METRIFUDIL
🧪 Phase II
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🧪 Phase II
Cc1ccccc1CNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL331382
Name METRIFUDIL
Phase Phase II
Structure Type MOL
InChI Key OOEMZCZWZXHBKW-SCFUHWHPSA-N

Known Names

Metrifudil TH 322 TH-322
10
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names

Molecular Properties

371.4
MW (Da)
0.36
ALogP
9
HBA
4
HBD
125.5
PSA (Ų)
0.51
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -dil

Extended Properties

Molecular Formula C18H21N5O4
MW 371.40
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.29

Activity Summary

Ki 9 meas. best 7.62
IC50 4 meas. best 7.26
EC50 1 meas. best 4.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A2a
CHEMBL302
 Ki 7.62 7.61 24.1 2
Adenosine receptor A3
CHEMBL3360
 Ki 7.42 6.93 38.0 2
Adenosine receptor A1
CHEMBL226
 Ki 7.41 7.41 39.0 1
Adenosine receptor A3
CHEMBL256
 Ki 7.33 7.33 47.0 1
Unchecked
CHEMBL612545
 IC50 7.26 7.26 55.0 1
Adenosine receptor A1
CHEMBL318
 Ki 7.22 7.115 59.6 2
Adenosine receptor A2a
CHEMBL251
 Ki 6.12 6.12 760.0 1
HL-60
CHEMBL383
 IC50 5.48 5.48 3300.0 1
CCRF-CEM
CHEMBL382
 IC50 4.85 4.85 14000.0 1
Cavia porcellus
CHEMBL369
 EC50 4.43 4.43 37000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A2a Ki = 24.1 nM 7.62 Binding affinity to adenosine A2A receptor in rat striatal membranes by measurin... 7707320
Adenosine receptor A2a Ki = 25.0 nM 7.6 Displacement of [3H]-CGS- 21680 from adenosine A2A receptor of rat striatal tiss... 10479279
Adenosine receptor A3 Ki = 38.0 nM 7.42 Inhibition of [125I]AB-MECA binding to rat Adenosine A3 receptor expressed in CH... 15771421
Adenosine receptor A1 Ki = 39.0 nM 7.41 Inhibition of [3H]R-PIA binding to human Adenosine A1 receptor expressed in CHO ... 15771421
Adenosine receptor A3 Ki = 47.0 nM 7.33 Inhibition of [125I]-AB-MECA binding to human Adenosine A3 receptor expressed in... 15771421
Unchecked IC50 = 55.0 nM 7.26 In vitro inhibition of isoprenaline-stimulated cAMP accumulation in DDT1-MF2 cel... 10479279
Adenosine receptor A1 Ki = 59.6 nM 7.22 Binding affinity to adenosine A1 receptor in rat brain membranes by measuring di... 7707320
Adenosine receptor A1 Ki = 98.0 nM 7.01 Displacement of [3H]R-PIA from adenosine A1 receptor of Wistar rat forebrain 10479279
Adenosine receptor A3 Ki = 360.0 nM 6.44 Binding affinity determined by displacement of specific binding of [125I]N-(4-am... 7707320
Adenosine receptor A2a Ki = 760.0 nM 6.12 Inhibition of [3H]-CGS- 21680 binding to human Adenosine A2A receptor expressed ... 15771421
HL-60 IC50 = 3300.0 nM 5.48 Antitumor activity against human HL60 cells after 72 hrs by Calcein AM assay 17418578
CCRF-CEM IC50 = 14000.0 nM 4.85 Antitumor activity against human CEM cells after 72 hrs by Calcein AM assay 17418578
Cavia porcellus EC50 = 37000.0 nM 4.43 Negative inotropy effect in isolated guinea pig atria. 10479279

Literature References

PubMed DOI Target Context # Activities
10479279 10.1021/jm960682u Rattus norvegicus 5
15771421 10.1021/jm049580r Adenosine receptor A3 3
10479279 10.1021/jm960682u Mus musculus 2
3012086 10.1021/jm00156a016 Adenosine A2 receptor 2
7707320 10.1021/jm00007a014 Adenosine receptor A2a 1
17417631 10.1038/nchembio873 Unchecked 1
17418578 10.1016/j.bmc.2007.03.038 Triticum aestivum 1
17418578 10.1016/j.bmc.2007.03.038 Amaranthus 1
15771421 10.1021/jm049580r Adenosine receptor A2b 1
15771421 10.1021/jm049580r Adenosine receptor A2a 1
15771421 10.1021/jm049580r Adenosine receptor A1 1
3012086 10.1021/jm00156a016 ADMET 1
7707320 10.1021/jm00007a014 Adenosine receptor A3 1
11063610 10.1021/jm000287a Phosphoglycerate kinase 1
7707320 10.1021/jm00007a014 Adenosine receptor A1 1
9822549 10.1021/jm9802620 Unchecked 1
10479279 10.1021/jm960682u Gerbillinae 1
10479279 10.1021/jm960682u Cavia porcellus 1
10479279 10.1021/jm960682u Unchecked 1
10479279 10.1021/jm960682u Adenosine receptor A2a 1

Data from ChEMBL 36 via Core Engine