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Compound Detail

CHEMBL158897

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O=C(NCCCCCCNC(=O)ON=C1CCCCC1)ON=C1CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL158897
Phase Preclinical
Structure Type MOL
InChI Key RXSVYGIGWRDVQC-UHFFFAOYSA-N
8
Targets
11
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

394.5
MW (Da)
4.64
ALogP
6
HBA
2
HBD
101.4
PSA (Ų)
0.34
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H34N4O4
MW 394.52
Aromatic Rings 0
Heavy Atoms 28
NP-Likeness -0.37

Activity Summary

IC50 11 meas. best 7.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Diacylglycerol lipase-beta
CHEMBL5521
 IC50 7.22 7.22 60.0 1
Diacylglycerol lipase-alpha
CHEMBL5545
 IC50 7.22 5.3275 60.0 4
Fatty-acid amide hydrolase 1
CHEMBL3229
 IC50 5.65 5.65 2240.0 1
Neutral cholesterol ester hydrolase 1
CHEMBL5048
 IC50 5.0 5.0 10000.0 1
Platelet-activating factor acetylhydrolase
CHEMBL3514
 IC50 4.96 4.96 11000.0 1
Phosphatidylserine lipase ABHD16A
CHEMBL6168
 IC50 4.64 4.64 23000.0 1
Fatty-acid amide hydrolase 1
CHEMBL2243
 IC50 4.16 4.16 70000.0 1
Secreted mono- and diacylglycerol lipase LIP1
CHEMBL3608197
 IC50 4.12 4.12 75250.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Diacylglycerol lipase-alpha IC50 = 60.0 nM 7.22 Inhibition of human recombinant DAGLalpha overexpressed in african green monkey ... 18657971
Diacylglycerol lipase-beta IC50 = 60.0 nM 7.22 Inhibition of human recombinant DAGLbeta overexpressed in african green monkey C... 18657971
Fatty-acid amide hydrolase 1 IC50 = 2240.0 nM 5.65 Inhibition of rat histidine tagged FAAH expressed in Escherichia coli by coumari... 22738638
Diacylglycerol lipase-alpha IC50 = 5011.87 nM 5.3 Inhibition of human C-terminal HA-tagged DAGLalpha expressed in HEK293F cell mem... 27394666
Neutral cholesterol ester hydrolase 1 IC50 = 10000.0 nM 5.0 Inhibition of recombinant KIAA1363 transfected in HEK293T cells by SDS-PAGE usin... 18657971
Platelet-activating factor acetylhydrolase IC50 = 11000.0 nM 4.96 Inhibition of recombinant PLA2g7 transfected in HEK293T cells by SDS-PAGE using ... 18657971
Phosphatidylserine lipase ABHD16A IC50 = 23000.0 nM 4.64 Inhibition of recombinant BAT5 transfected in HEK293T cells by SDS-PAGE using rh... 18657971
Diacylglycerol lipase-alpha IC50 = 25118.86 nM 4.6 Inhibition of human C-terminal HA-tagged DAGLalpha expressed in HEK293F cell mem... 27394666
Diacylglycerol lipase-alpha IC50 = 65000.0 nM 4.19 Inhibition of human DAGLalpha 22738638
Fatty-acid amide hydrolase 1 IC50 = 70000.0 nM 4.16 Inhibition of recombinant FAAH transfected in HEK293T cells by SDS-PAGE using rh... 18657971
Secreted mono- and diacylglycerol lipase LIP1 IC50 = 75250.0 nM 4.12 Inhibition of Malassezia globosa CBS 7966 LIP1 using pNPA substrate 26199121

Literature References

PubMed DOI Target Context # Activities
18657971 10.1016/j.bmcl.2008.06.091 Diacylglycerol lipase-alpha 4
18657971 10.1016/j.bmcl.2008.06.091 Diacylglycerol lipase-beta 4
22738638 10.1016/j.bmcl.2012.05.101 Diacylglycerol lipase-alpha 4
18657971 10.1016/j.bmcl.2008.06.091 Platelet-activating factor acetylhydrolase 3
18657971 10.1016/j.bmcl.2008.06.091 Fatty-acid amide hydrolase 1 3
18657971 10.1016/j.bmcl.2008.06.091 Neutral cholesterol ester hydrolase 1 3
18657971 10.1016/j.bmcl.2008.06.091 Phosphatidylserine lipase ABHD16A 3
18657971 10.1016/j.bmcl.2008.06.091 Acetylcholinesterase 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
27394666 10.1016/j.bmcl.2016.06.076 Diacylglycerol lipase-alpha 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
26199121 10.1016/j.bmcl.2015.07.005 Secreted mono- and diacylglycerol lipase LIP1 2
22738638 10.1016/j.bmcl.2012.05.101 Fatty-acid amide hydrolase 1 2
22738638 10.1016/j.bmcl.2012.05.101 Unchecked 2
18657971 10.1016/j.bmcl.2008.06.091 Lysophosphatidylserine lipase ABHD12 2
18657971 10.1016/j.bmcl.2008.06.091 Hormone-sensitive lipase 1
22738638 10.1016/j.bmcl.2012.05.101 Monoglyceride lipase 1
3806604 10.1021/jm00384a011 Unchecked 1
18657971 10.1016/j.bmcl.2008.06.091 Monoacylglycerol lipase ABHD6 1
18657971 10.1016/j.bmcl.2008.06.091 Monoglyceride lipase 1

Data from ChEMBL 36 via Core Engine