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Compound Detail

CHEMBL3770726

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O=C(N[C@H]1CNC1=O)OCCCCC1CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3770726
Phase Preclinical
Structure Type MOL
InChI Key FNLUJRBWJBUJTC-LBPRGKRZSA-N
3
Targets
10
Activities
1
Assay Types
11
PK Parameters
13
Publications
0
Known Names

Molecular Properties

268.4
MW (Da)
1.96
ALogP
3
HBA
2
HBD
67.4
PSA (Ų)
0.57
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 C14H24N2O3
MW 268.36
Aromatic Rings 0
Heavy Atoms 19
NP-Likeness 0.27

Activity Summary

IC50 10 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
N-acylethanolamine-hydrolyzing acid amidase
CHEMBL4349
 IC50 8.22 7.535 6.0 6
N-acylethanolamine-hydrolyzing acid amidase
CHEMBL2034805
 IC50 7.89 7.5467 13.0 3
Acid ceramidase
CHEMBL5463
 IC50 5.2 5.2 6270.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 139.0 mL.min-1.kg-1 Mus musculus
Cmax 1608.0 ng/kg Mus musculus
T1/2 0.08333 hr Rattus norvegicus
T1/2 0.2 hr Rattus norvegicus
T1/2 0.08333 hr Mus musculus
T1/2 0.6833 hr Mus musculus
T1/2 0.08333 hr Rattus norvegicus
T1/2 0.08333 hr Mus musculus
T1/2 0.25 hr Mus musculus
T1/2 0.6833 hr Mus musculus
T1/2 0.2 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
N-acylethanolamine-hydrolyzing acid amidase IC50 = 6.0 nM 8.22 Inhibition of human NAAA 32191459
N-acylethanolamine-hydrolyzing acid amidase IC50 = 13.0 nM 7.89 Inhibition of rat NAAA 32191459
N-acylethanolamine-hydrolyzing acid amidase IC50 = 27.0 nM 7.57 Inhibition of recombinant human NAAA expressed in HEK293 cells after 30 mins by ... 26866968
N-acylethanolamine-hydrolyzing acid amidase IC50 = 27.0 nM 7.57 Inhibition recombinant human NAAA expressed in HEK293 cells after 10 mins 27766867
N-acylethanolamine-hydrolyzing acid amidase IC50 = 27.0 nM 7.57 Inhibition of recombinant human NAAA expressed in HEK cells 32191459
N-acylethanolamine-hydrolyzing acid amidase IC50 = 28.0 nM 7.55 Inhibition of rat NAAA expressed in HEK cells after 30 mins 27915171
N-acylethanolamine-hydrolyzing acid amidase IC50 = 63.0 nM 7.2 Inhibition of recombinant Sprague-Dawley rat NAAA expressed in HEK293 cells afte... 27766867
N-acylethanolamine-hydrolyzing acid amidase IC50 = 73.0 nM 7.14 Inhibition of human NAAA expressed in HEK293 cells preincubated for 10 mins foll... 26866968
N-acylethanolamine-hydrolyzing acid amidase IC50 = 73.0 nM 7.14 Inhibition of recombinant human NAAA expressed in HEK cells after 30 mins 27915171
Acid ceramidase IC50 = 6270.0 nM 5.2 Inhibition of human acid ceramidase by UPLC/MS analysis 26866968

Literature References

PubMed DOI Target Context # Activities
27766867 10.1021/acs.jmedchem.6b00538 ADMET 6
32191459 10.1021/acs.jmedchem.0c00191 N-acylethanolamine-hydrolyzing acid amidase 3
26866968 10.1016/j.ejmech.2016.01.046 Plasma 2
26866968 10.1016/j.ejmech.2016.01.046 N-acylethanolamine-hydrolyzing acid amidase 2
27915171 10.1016/j.ejmech.2016.11.039 N-acylethanolamine-hydrolyzing acid amidase 2
27766867 10.1021/acs.jmedchem.6b00538 N-acylethanolamine-hydrolyzing acid amidase 2
26866968 10.1016/j.ejmech.2016.01.046 No relevant target 1
26866968 10.1016/j.ejmech.2016.01.046 Liver microsome 1
26866968 10.1016/j.ejmech.2016.01.046 ADMET 1
26866968 10.1016/j.ejmech.2016.01.046 Fatty-acid amide hydrolase 1 1
26866968 10.1016/j.ejmech.2016.01.046 Acid ceramidase 1
26866968 10.1016/j.ejmech.2016.01.046 Unchecked 1
27766867 10.1021/acs.jmedchem.6b00538 Mus musculus 1

Data from ChEMBL 36 via Core Engine