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Compound Detail

CHEMBL3186509

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O=C(CCN1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1)c1ccc2[nH]c(=O)oc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3186509
Phase Preclinical
Structure Type MOL
InChI Key JMSUDQYHPSNBSN-UHFFFAOYSA-N
9
Targets
30
Activities
1
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

478.3
MW (Da)
3.96
ALogP
6
HBA
1
HBD
95.8
PSA (Ų)
0.54
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H21Cl2N3O5
MW 478.33
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.22

Activity Summary

IC50 30 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Autotaxin
CHEMBL3691
 IC50 8.96 8.2189 1.1 19
Autotaxin
CHEMBL3826871
 IC50 8.77 8.66 1.7 2
Autotaxin
CHEMBL3826870
 IC50 6.51 6.03 307.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 6.32 5.945 480.0 2
MCF7
CHEMBL387
 IC50 5.64 5.64 2310.0 1
MDA-MB-231
CHEMBL400
 IC50 5.38 5.38 4170.0 1
A549
CHEMBL392
 IC50 5.09 5.09 8210.0 1
RAW264.7
CHEMBL612557
 IC50 5.02 5.02 9580.0 1
NCI-H2228
CHEMBL1075536
 IC50 4.95 4.95 11270.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 31.0 mL.min-1.kg-1 Rattus norvegicus
F 43.0 % Rattus norvegicus
F 43.0 % Rattus norvegicus
T1/2 1.2 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Autotaxin IC50 = 1.1 nM 8.96 Inhibition of ATX (unknown origin) assessed as decrease in choline release 29798825
Autotaxin IC50 = 1.7 nM 8.77 Inhibition of recombinant mouse ATX expressed in HEK293 cells using LPC 17:0 as ... 29620892
Autotaxin IC50 = 1.7 nM 8.77 Inhibition of recombinant human ATX beta expressed in HEK293 cells using LPC as ... 28743508
Autotaxin IC50 = 1.7 nM 8.77 Inhibition of ATX (unknown origin) 37976710
Autotaxin IC50 = 2.7 nM 8.57 Inhibition of human ATX pre-incubated for 45 mins before fluorogenic substrate-3... 32479084
Autotaxin IC50 = 2.8 nM 8.55 Inhibition of recombinant human ATX expressed in HEK293 cells using FS3 as subst... 26745766
Autotaxin IC50 = 2.8 nM 8.55 Inhibition of human ATX expressed in HEK293 cells using FS-3 as substrate preinc... 27982588
Autotaxin IC50 = 2.8 nM 8.55 Inhibition of recombinant mouse ATX expressed in HEK293 cells using FS3 as subst... 29620892
Autotaxin IC50 = 2.8 nM 8.55 Inhibition of recombinant human ATX beta expressed in HEK293 cells using FS-3 as... 28743508
Autotaxin IC50 = 2.8 nM 8.55 Inhibition of recombinant ATX (unknown origin) expressed in HEK293 cells using F... 27544588
Autotaxin IC50 = 2.8 nM 8.55 Inhibition of human ATX by fluorogenic substrate-3 assay 32479084
Autotaxin IC50 = 3.0 nM 8.52 Inhibition of human recombinant ATX using Rac-1-Palmitoyl-glycero-3-phosphocholi... 27780639
Autotaxin IC50 = 3.0 nM 8.52 Inhibition of human ATX expressed in HEK293 cells using FS-3 as substrate after ... 28165241
Autotaxin IC50 = 3.0 nM 8.52 Inhibition of human full length ATX expressed in HEK cells using FS-3 as substra... 29259743
Autotaxin IC50 = 3.7 nM 8.43 Negative allosteric modulation activity against human ATX using FS-3 as substrat... 35436669
Autotaxin IC50 = 4.3 nM 8.37 Inhibition of human C-terminal His6-tagged ATX beta expressed in Sf9 insect cell... 32535330
Autotaxin IC50 = 8.4 nM 8.08 Inhibition of recombinant full length human C-terminal His-tagged autotaxin expr... 27660691
Autotaxin IC50 = 44.0 nM 7.36 Inhibition of autotaxin in healthy human plasma assessed as reduction in LPA lev... 27660691
Autotaxin IC50 = 101.0 nM 7.0 Inhibition of ATX in human whole blood assessed as decrease in LPA levels after ... 29620892
Autotaxin IC50 = 100.0 nM 7.0 Inhibition of autotaxin in healthy human whole blood assessed as reduction in LP... 27660691

Literature References

PubMed DOI Target Context # Activities
26745766 10.1021/acs.jmedchem.5b01599 Rattus norvegicus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
27660691 10.1021/acsmedchemlett.6b00207 Autotaxin 3
29620892 10.1021/acs.jmedchem.8b00232 Autotaxin 3
28743508 10.1016/j.bmcl.2017.07.022 Autotaxin 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
32479084 10.1021/acs.jmedchem.0c00506 Autotaxin 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
29259743 10.1021/acsmedchemlett.7b00312 Autotaxin 2
36702053 10.1016/j.ejmech.2023.115130 No relevant target 2
29798825 10.1016/j.bmcl.2018.05.030 No relevant target 2
26190462 10.1016/j.bmc.2015.06.054 MeWo 2
27780639 10.1016/j.bmcl.2016.10.036 Autotaxin 2
26745766 10.1021/acs.jmedchem.5b01599 Plasma 2
29798825 10.1016/j.bmcl.2018.05.030 Autotaxin 1
29798825 10.1016/j.bmcl.2018.05.030 Voltage-gated inwardly rectifying potassium channel KCNH2 1
29620892 10.1021/acs.jmedchem.8b00232 Rattus norvegicus 1
37976710 10.1016/j.ejmech.2023.115944 Autotaxin 1
28165241 10.1021/acs.jmedchem.6b01743 Autotaxin 1
27982588 10.1021/acs.jmedchem.6b01597 Autotaxin 1

Data from ChEMBL 36 via Core Engine