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Compound Detail

CHEMBL2064166

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C[C@@H]1OC(=O)[C@@H]1NC(=O)OCCCCCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2064166
Phase Preclinical
Structure Type MOL
InChI Key PTVDTLVLQXSSEC-GXTWGEPZSA-N
2
Targets
10
Activities
1
Assay Types
5
PK Parameters
13
Publications
0
Known Names

Molecular Properties

291.4
MW (Da)
2.44
ALogP
4
HBA
1
HBD
64.6
PSA (Ų)
0.62
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 C16H21NO4
MW 291.35
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 0.50

Activity Summary

IC50 10 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
N-acylethanolamine-hydrolyzing acid amidase
CHEMBL4349
 IC50 8.15 8.088 7.0 5
N-acylethanolamine-hydrolyzing acid amidase
CHEMBL2034805
 IC50 7.3 7.214 50.0 5

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.838 hr -
T1/2 3.237 hr -
T1/2 2.24 hr -
T1/2 0.19 hr Bos taurus
T1/2 0.002778 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 = 7.0 nM 8.15 Inhibition of C-terminal His-6-tagged recombinant human spleen NAAA enzyme expre... 23991897
N-acylethanolamine-hydrolyzing acid amidase IC50 = 7.0 nM 8.15 UPLC/MS Assay: NAAA protein preparation (10 ug) was pre-incubated with various c... -
N-acylethanolamine-hydrolyzing acid amidase IC50 = 7.0 nM 8.15 Inhibition of NAAA (unknown origin) 33900772
N-acylethanolamine-hydrolyzing acid amidase IC50 = 7.3 nM 8.14 Inhibition of human recombinant His6-tagged NAAA expressed in HEK293 cells using... 24900487
N-acylethanolamine-hydrolyzing acid amidase IC50 = 14.0 nM 7.85 Fluorogenic Assay: The assay was run in Optiplate 96-wells black plates, in a to... -
N-acylethanolamine-hydrolyzing acid amidase IC50 = 50.0 nM 7.3 Inhibition of Sprague Dawley rat lung native NAAA enzyme using heptadecenoyletha... 23991897
N-acylethanolamine-hydrolyzing acid amidase IC50 = 50.0 nM 7.3 Inhibition of NAAA in Sprague-Dawley rat lung assessed as inhibition of hydrolys... 25380517
N-acylethanolamine-hydrolyzing acid amidase IC50 = 50.0 nM 7.3 Enzymatic Assay: Lysosomal NAAA protein preparation were obtained by homogenizin... -
N-acylethanolamine-hydrolyzing acid amidase IC50 = 52.48 nM 7.28 Inhibition of NAAA in Sprague-Dawley rat lung assessed as inhibition of hydrolys... 25380517
N-acylethanolamine-hydrolyzing acid amidase IC50 = 130.0 nM 6.89 Inhibition of rat recombinant NAAA expressed in HEK293 cells using heptadecenoyl... 22515328

Literature References

PubMed DOI Target Context # Activities
24900487 10.1021/ml300056y N-acylethanolamine-hydrolyzing acid amidase 5
22515328 10.1021/jm300349j No relevant target 3
23991897 10.1021/jm400739u N-acylethanolamine-hydrolyzing acid amidase 2
25380517 10.1021/jm501455s N-acylethanolamine-hydrolyzing acid amidase 2
22515328 10.1021/jm300349j N-acylethanolamine-hydrolyzing acid amidase 1
22515328 10.1021/jm300349j Albumin 1
22515328 10.1021/jm300349j Plasma 1
24900487 10.1021/ml300056y Fatty-acid amide hydrolase 1 1
24900487 10.1021/ml300056y Acid ceramidase 1
23991897 10.1021/jm400739u Unchecked 1
23991897 10.1021/jm400739u Acid ceramidase 1
23991897 10.1021/jm400739u Fatty-acid amide hydrolase 1 1
33900772 10.1021/acs.jmedchem.1c00076 N-acylethanolamine-hydrolyzing acid amidase 1

Data from ChEMBL 36 via Core Engine