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Compound Detail

CHEMBL576786

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O=C(Oc1ccc([N+](=O)[O-])cc1)N1CCC(C(O)(c2ccc3c(c2)OCO3)c2ccc3c(c2)OCO3)CC1

Basic Information

ChEMBL ID CHEMBL576786
Phase Preclinical
Structure Type MOL
InChI Key SEGYOKHGGFKMCX-UHFFFAOYSA-N
8
Targets
38
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

520.5
MW (Da)
4.20
ALogP
9
HBA
1
HBD
129.8
PSA (Ų)
0.39
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H24N2O9
MW 520.49
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness -0.61

Activity Summary

IC50 38 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Monoglyceride lipase
CHEMBL4191
IC50 8.7 7.3856 2.0 18
Fatty-acid amide hydrolase 1
CHEMBL2243
IC50 8.4 6.0567 4.0 3
Monoglyceride lipase
CHEMBL5774
IC50 8.22 8.12 6.0 7
Unchecked
CHEMBL612545
IC50 8.1 8.1 8.0 1
Monoglyceride lipase
CHEMBL3321
IC50 7.6 7.6 25.0 1
Fatty-acid amide hydrolase 1
CHEMBL3229
IC50 6.01 6.01 974.0 1
Monoacylglycerol lipase ABHD6
CHEMBL5010
IC50 5.49 5.49 3270.0 1
Fatty-acid amide hydrolase 1
CHEMBL3455
IC50 5.4 5.365 4000.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Monoglyceride lipase IC50 = 2.0 nM 8.7 Inhibition of human MAGL expressed in monkey COS7 cells 23455058
Monoglyceride lipase IC50 = 2.0 nM 8.7 Inhibition of human MAGL expressed in COS7 cells using endogenous 2-AG substrate 22738638
Fatty-acid amide hydrolase 1 IC50 = 4.0 nM 8.4 Inhibition of recombinant FAAH expressed in Cos7 cells after 30 mins by using an... 19029917
Monoglyceride lipase IC50 = 5.6 nM 8.25 Inhibition of recombinant human MAGL using fluorogenic-7HCA as substrate preincu... 29498843
Monoglyceride lipase IC50 = 6.0 nM 8.22 Inhibition of human MGL 19583260
Monoglyceride lipase IC50 = 6.0 nM 8.22 Inhibition of recombinant MAGL expressed in Cos7 cells after 30 mins by using 2-... 19029917
Monoglyceride lipase IC50 = 6.0 nM 8.22 Inhibition of MAGL-mediated 2-arachidonoylglycerol hydrolysis in mouse brain mem... 23455058
Monoglyceride lipase IC50 = 6.0 nM 8.22 Inhibition of MAGL (unknown origin) 27267002
Monoglyceride lipase IC50 = 6.0 nM 8.22 Inhibition of MAGL in mouse brain membrane using 2-AG as substrate by LC-MS anal... 33766770
Monoglyceride lipase IC50 = 8.0 nM 8.1 Inhibition of MAGL in C57B1/6J mouse brain membrane after 30 mins by using 2-AG ... 19029917
Monoglyceride lipase IC50 = 8.0 nM 8.1 Inhibition of mouse MAGL 38428273
Monoglyceride lipase IC50 = 8.0 nM 8.1 Inhibition of mouse MAGL 32429662
Monoglyceride lipase IC50 = 8.0 nM 8.1 Inhibition of recombinant MAGL (unknown origin) expressed in monkey COS7 cells 23455058
Monoglyceride lipase IC50 = 8.0 nM 8.1 Inhibition of mouse recombinant MAGL expressed in african green monkey COS7 cell... 21982493
Unchecked IC50 = 8.0 nM 8.1 Inhibition of MAGL 19088712
Monoglyceride lipase IC50 = 10.0 nM 8.0 Inhibition of MAGL in mouse brain membrane 20099888
Monoglyceride lipase IC50 = 10.0 nM 8.0 Inhibition of MAGL 23036333
Monoglyceride lipase IC50 = 25.0 nM 7.6 Inhibition of rat MAGL expressed in monkey COS7 cells 23455058
Monoglyceride lipase IC50 = 37.0 nM 7.43 Inhibition of human MAGL assessed as [3H]-2-OG hydrolysis preincubated for 30 mi... 23036333
Monoglyceride lipase IC50 = 47.0 nM 7.33 Inhibition of human recombinant MAGL using 4-nitrophenylacetate as substrate inc... 37976705

Literature References

PubMed DOI Target Context # Activities
19029917 10.1038/nchembio.129 Mus musculus 85
22738638 10.1016/j.bmcl.2012.05.101 Diacylglycerol lipase-alpha 8
23455058 10.1016/j.ejmech.2013.01.050 Monoglyceride lipase 6
35522977 10.1021/acs.jmedchem.1c01806 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19029917 10.1038/nchembio.129 Monoglyceride lipase 4
19029917 10.1038/nchembio.129 Cytosolic phospholipase A2 3
22738638 10.1016/j.bmcl.2012.05.101 Monoglyceride lipase 3
19029917 10.1038/nchembio.129 Fatty-acid amide hydrolase 1 3
31714779 10.1021/acs.jmedchem.9b01679 N2a 2
23036333 10.1016/j.bmc.2012.09.011 Fatty-acid amide hydrolase 1 2
19029917 10.1038/nchembio.129 Diacylglycerol lipase-beta 2
19029917 10.1038/nchembio.129 Diacylglycerol lipase-alpha 2
23036333 10.1016/j.bmc.2012.09.011 Monoglyceride lipase 2
19088712 10.1038/nchembio0109-8 Unchecked 2
23455058 10.1016/j.ejmech.2013.01.050 Fatty-acid amide hydrolase 1 2
29498843 10.1021/acs.jmedchem.8b00070 Monoglyceride lipase 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
22738638 10.1016/j.bmcl.2012.05.101 Fatty-acid amide hydrolase 1 2
30715876 10.1021/acs.jmedchem.8b01483 Monoglyceride lipase 2

Data from ChEMBL 36 via Core Engine