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Compound Detail

CHEMBL175854

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O=C(CCCCCc1ccccc1)c1nc2ncccc2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL175854
Phase Preclinical
Structure Type MOL
InChI Key VPZHQLPAKFVGKX-UHFFFAOYSA-N
7
Targets
24
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

294.4
MW (Da)
4.21
ALogP
4
HBA
0
HBD
56.0
PSA (Ų)
0.48
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 C18H18N2O2
MW 294.35
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -0.43

Activity Summary

IC50 15 meas. best 9.0
Ki 9 meas. best 10.03

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Fatty-acid amide hydrolase 1
CHEMBL2243
 Ki 10.03 9.865 0.1 4
Fatty-acid amide hydrolase 1
CHEMBL3229
 Ki 9.7 9.7 0.2 4
Fatty-acid amide hydrolase 1
CHEMBL3455
 Ki 9.7 9.7 0.2 1
Fatty-acid amide hydrolase 1
CHEMBL2243
 IC50 9.0 9.0 1.0 3
Liver carboxylesterase 1
CHEMBL2265
 IC50 9.0 9.0 1.0 2
Fatty-acid amide hydrolase 1
CHEMBL3229
 IC50 8.54 8.414 2.9 5
Diacylglycerol lipase-alpha
CHEMBL5545
 IC50 7.43 7.415 37.1 2
Diacylglycerol lipase-alpha
CHEMBL5180
 IC50 6.3 6.3 501.2 1
Unchecked
CHEMBL612545
 IC50 5.0 5.0 10000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Fatty-acid amide hydrolase 1 Ki = 0.094 nM 10.03 Inhibition of human recombinant FAAH 18053726
Fatty-acid amide hydrolase 1 Ki = 0.094 nM 10.03 Binding affinity for human fatty acid amide hydrolase 16078824
Fatty-acid amide hydrolase 1 Ki = 0.2 nM 9.7 Inhibition of rat FAAH assessed as reduction in [14C]oleamide conversion to olei... 27766867
Fatty-acid amide hydrolase 1 Ki = 0.2 nM 9.7 Inhibition of FAAH 21764305
Fatty-acid amide hydrolase 1 Ki = 0.2 nM 9.7 Inhibition of FAAH 18983142
Fatty-acid amide hydrolase 1 Ki = 0.2 nM 9.7 Inhibition of rat FAAH 18053726
Fatty-acid amide hydrolase 1 Ki = 0.2 nM 9.7 Binding affinity for rat fatty acid amide hydrolase 16078824
Fatty-acid amide hydrolase 1 Ki = 0.2 nM 9.7 Inhibitor affinity towards enzymes of class serine hydrolase was determined usin... 15713400
Fatty-acid amide hydrolase 1 Ki = 0.2 nM 9.7 Inhibitory constant determined against recombinant Fatty-acid amide hydrolase fr... 15771430
Liver carboxylesterase 1 IC50 = 1.0 nM 9.0 Inhibitory concentration against Triacylglycerol hydrolase 15771430
Fatty-acid amide hydrolase 1 IC50 = 1.0 nM 9.0 Inhibition of FAAH (unknown origin) 23455058
Liver carboxylesterase 1 IC50 = 1.0 nM 9.0 Inhibitory concentration of triacylgylcerol hydrolase using FP-Rh radioligand 15713400
Fatty-acid amide hydrolase 1 IC50 = 1.0 nM 9.0 Inhibitory concentration of fatty acid amide hydrolase using FP-Rh radioligand 15713400
Fatty-acid amide hydrolase 1 IC50 = 1.0 nM 9.0 Inhibitory concentration against Fatty-acid amide hydrolase 15771430
Fatty-acid amide hydrolase 1 IC50 = 2.9 nM 8.54 Inhibition of FAAH in rat brain microsomes using N-(2-hydroxyethyl)-4-pyren-1-yl... 27989417
Fatty-acid amide hydrolase 1 IC50 = 2.9 nM 8.54 Inhibition of Sprague-Dawley rat brain microsomal FAAH using N-(2-hydroxyethyl)-... -
Fatty-acid amide hydrolase 1 IC50 = 2.9 nM 8.54 Inhibition of Sprague-Dawley rat brain microsome FAAH assessed as reduction in 4... 22196515
Fatty-acid amide hydrolase 1 IC50 = 4.0 nM 8.4 Inhibition of FAAH in Sprague-Dawley rat brain microsomes assessed as N-(2-hydro... 23455058
Fatty-acid amide hydrolase 1 IC50 = 9.0 nM 8.05 Inhibition of FAAH from rat brain microsomes by RP-HPLC 20005725
Diacylglycerol lipase-alpha IC50 = 37.15 nM 7.43 Inhibition of full-length human DAGLalpha expressed in HEK293T cell membranes us... 26584396

Literature References

PubMed DOI Target Context # Activities
18053726 10.1016/j.bmc.2007.11.015 Unchecked 4
27394666 10.1016/j.bmcl.2016.06.076 Diacylglycerol lipase-alpha 2
15713400 10.1016/j.bmcl.2004.12.085 Fatty-acid amide hydrolase 1 2
16078824 10.1021/jm058183t Fatty-acid amide hydrolase 1 2
18053726 10.1016/j.bmc.2007.11.015 Fatty-acid amide hydrolase 1 2
15771430 10.1021/jm049614v Fatty-acid amide hydrolase 1 2
23455058 10.1016/j.ejmech.2013.01.050 Fatty-acid amide hydrolase 1 2
20005725 10.1016/j.bmc.2009.11.028 Fatty-acid amide hydrolase 1 1
27766867 10.1021/acs.jmedchem.6b00538 Fatty-acid amide hydrolase 1 1
27989417 10.1016/j.bmc.2016.11.025 Fatty-acid amide hydrolase 1 1
26584396 10.1021/acs.jmedchem.5b01627 Diacylglycerol lipase-alpha 1
- 10.1039/C4MD00181H Fatty-acid amide hydrolase 1 1
23455058 10.1016/j.ejmech.2013.01.050 Monoglyceride lipase 1
22196515 10.1016/j.bmc.2011.11.027 Fatty-acid amide hydrolase 1 1
21764305 10.1016/j.bmcl.2011.06.096 Fatty-acid amide hydrolase 1 1
20005725 10.1016/j.bmc.2009.11.028 Cytosolic phospholipase A2 1
18983142 10.1021/jm800311k Fatty-acid amide hydrolase 1 1
15713400 10.1016/j.bmcl.2004.12.085 Liver carboxylesterase 1 1
15713400 10.1016/j.bmcl.2004.12.085 Unchecked 1
15771430 10.1021/jm049614v Liver carboxylesterase 1 1

Data from ChEMBL 36 via Core Engine