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Compound Detail

CHEMBL146227

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O=c1[nH]c2ccccc2cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL146227
Phase Preclinical
Structure Type MOL
InChI Key BERPCVULMUPOER-UHFFFAOYSA-N
6
Targets
13
Activities
2
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

161.2
MW (Da)
1.23
ALogP
2
HBA
2
HBD
53.1
PSA (Ų)
0.61
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C9H7NO2
MW 161.16
Aromatic Rings 2
Heavy Atoms 12
NP-Likeness -0.17

Activity Summary

IC50 11 meas. best 8.4
Kd 2 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D-amino-acid oxidase
CHEMBL5485
 IC50 8.4 7.8275 4.0 4
D-amino-acid oxidase
CHEMBL5485
 Kd 7.89 7.89 13.0 1
D-amino-acid oxidase
CHEMBL5756
 IC50 7.03 6.85 94.0 2
D-amino-acid oxidase
CHEMBL6172
 IC50 7.0 7.0 100.0 1
D-amino-acid oxidase
CHEMBL6172
 Kd 6.82 6.82 150.0 1
D-aspartate oxidase
CHEMBL5887
 IC50 6.07 6.07 855.0 1
Mushroom tyrosinase
CHEMBL6066154
 IC50 5.56 5.56 2740.0 1
Unchecked
CHEMBL612545
 IC50 4.62 4.62 24000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 46.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 34.13 nM Rattus norvegicus
F 0.9 % Rattus norvegicus
Fu 0.22 - Rattus norvegicus
Fu 0.43 - Rattus norvegicus
Fu 0.26 - Rattus norvegicus
t1/2 - - Rattus norvegicus
Vd 10.8 ml/min.Kg Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D-amino-acid oxidase IC50 = 4.0 nM 8.4 Inhibition of human recombinant DAAO expressed in sf9 insect cells assessed as d... 19438227
D-amino-acid oxidase IC50 = 6.9 nM 8.16 Inhibition of human recombinant DAAO after 30 mins by plate reader analysis 23566269
D-amino-acid oxidase Kd = 13.0 nM 7.89 Binding affinity to biotinylated human recombinant DAAO by Biacore assay 19438227
D-amino-acid oxidase IC50 = 42.0 nM 7.38 Inhibition of DAAO (unknown origin) by cell based assay 23566269
D-amino-acid oxidase IC50 = 43.0 nM 7.37 Inhibition of human recombinant DAAO using D-alanine as substrate assessed as py... 27089209
D-amino-acid oxidase IC50 = 94.0 nM 7.03 Inhibition of rat spinal DAAO using D-alanine as substrate assessed as pyruvate ... 27089209
D-amino-acid oxidase IC50 = 100.0 nM 7.0 Inhibition of DAAO in porcine kidney homogenate using D-alanine as substrate ass... 27089209
D-amino-acid oxidase Kd = 150.0 nM 6.82 Binding affinity to pig kidney DAAO by ITC method 29472125
D-amino-acid oxidase IC50 = 215.0 nM 6.67 Inhibition of rat recombinant DAAO expressed in sf9 insect cells assessed as deg... 19438227
D-aspartate oxidase IC50 = 855.0 nM 6.07 Inhibition of human recombinant DDO expressed in sf9 insect cells assessed as de... 19438227
Mushroom tyrosinase IC50 = 2740.0 nM 5.56 Inhibition of mushroom tyrosinase using L-DOPA as substrate by spectrophotometri... 38823727
Unchecked IC50 = 24000.0 nM 4.62 Inhibition of H1N1 Influenza A endonuclease after 1 hr by fluorescence assay 24936242
Unchecked IC50 = 24000.0 nM 4.62 Endonuclease Assay: The PAN domain has been shown to cleave ssRNA as well as ssD... -

Literature References

PubMed DOI Target Context # Activities
19438227 10.1021/jm900128w Rattus norvegicus 9
19438227 10.1021/jm900128w Brain 5
19438227 10.1021/jm900128w D-amino-acid oxidase 3
27089209 10.1016/j.ejmech.2016.04.017 D-amino-acid oxidase 3
22607675 10.1016/j.bmcl.2012.04.096 Human immunodeficiency virus type 1 reverse transcriptase 3
19438227 10.1021/jm900128w ADMET 3
19438227 10.1021/jm900128w Unchecked 2
23566269 10.1021/jm400095b D-amino-acid oxidase 2
25408840 10.1021/ml500335z ADMET 2
19438227 10.1021/jm900128w MDCK 1
19438227 10.1021/jm900128w Plasma 1
19438227 10.1021/jm900128w No relevant target 1
19438227 10.1021/jm900128w D-aspartate oxidase 1
22607675 10.1016/j.bmcl.2012.04.096 Human immunodeficiency virus 1 1
22607675 10.1016/j.bmcl.2012.04.096 MT4 1
22607675 10.1016/j.bmcl.2012.04.096 Unchecked 1
23566269 10.1021/jm400095b ADMET 1
24936242 10.1021/ml4001112 Unchecked 1
- 10.1016/0960-894X(96)00031-5 Glutamate NMDA receptor 1
29472125 10.1016/j.bmc.2018.02.004 D-amino-acid oxidase 1

Data from ChEMBL 36 via Core Engine