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Compound Detail

CHEMBL3785379

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O=C1[C@H](c2ccc(F)cc2)[C@@H](c2ccc3c(c2)OCO3)N1C1CCN(C(=O)n2cncn2)CC1

Basic Information

ChEMBL ID CHEMBL3785379
Phase Preclinical
Structure Type MOL
InChI Key XRIROGBLGLPXQI-FGZHOGPDSA-N
5
Targets
18
Activities
1
Assay Types
4
PK Parameters
19
Publications
0
Known Names

Molecular Properties

463.5
MW (Da)
2.95
ALogP
7
HBA
0
HBD
89.8
PSA (Ų)
0.56
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H22FN5O4
MW 463.47
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -0.77

Activity Summary

IC50 18 meas. best 9.98

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Monoglyceride lipase
CHEMBL5774
IC50 9.98 9.715 0.1 2
Monoglyceride lipase
CHEMBL3321
IC50 9.8 9.214 0.2 5
Monoglyceride lipase
CHEMBL4191
IC50 9.7 8.1529 0.2 7
Unchecked
CHEMBL612545
IC50 9.59 9.27 0.3 2
Fatty-acid amide hydrolase 1
CHEMBL2243
IC50 5.54 5.465 2880.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 273.2 mL.min-1.g-1 Mus musculus
CL 123.8 mL.min-1.g-1 Homo sapiens
CL 200.0 mL.min-1.g-1 Mus musculus
CL 91.9 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Monoglyceride lipase IC50 = 0.105 nM 9.98 Inhibition of mouse MAGL using arachidonic acid as substrate preincubated with c... 38241614
Monoglyceride lipase IC50 = 0.159 nM 9.8 Inhibition of rat MAGL 38241614
Monoglyceride lipase IC50 = 0.198 nM 9.7 Inhibition of human MAGL 38241614
Monoglyceride lipase IC50 = 0.25 nM 9.6 Inhibition of rat MAGL 26888301
Monoglyceride lipase IC50 = 0.26 nM 9.59 Inhibition of rat MAGL expressed in human HeLa cells using 2-arachidonoylglycero... 38241614
Unchecked IC50 = 0.255 nM 9.59 Inhibition of cynomolgus monkey MAGL 38241614
Monoglyceride lipase IC50 = 0.357 nM 9.45 Inhibition of mouse MAGL using arachidonic acid as substrate preincubated with c... 38241614
Monoglyceride lipase IC50 = 0.825 nM 9.08 Inhibition of human MAGL 38241614
Monoglyceride lipase IC50 = 0.827 nM 9.08 Inhibition of rat MAGL 38241614
Unchecked IC50 = 1.117 nM 8.95 Inhibition of cynomolgus monkey MAGL 38241614
Monoglyceride lipase IC50 = 4.6 nM 8.34 Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escheri... 26888301
Monoglyceride lipase IC50 = 7.4 nM 8.13 Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escheri... 26888301
Monoglyceride lipase IC50 = 7.4 nM 8.13 Inhibition of human recombinant MAGL (1 to 303 residues) expressed in human HeLa... 38241614
Monoglyceride lipase IC50 = 10.0 nM 8.0 Inhibition of MAGL in rat brain membranes preincubated for 20 mins followed by f... 26888301
Monoglyceride lipase IC50 = 104.4 nM 6.98 Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escheri... 26888301
Monoglyceride lipase IC50 = 195.8 nM 6.71 Inhibition of recombinant C-terminal His6-tagged human MAGL expressed in Escheri... 26888301
Fatty-acid amide hydrolase 1 IC50 = 2880.0 nM 5.54 Inhibition of recombinant C-terminal His-tagged human FAAH expressed in sf21 cel... 26888301
Fatty-acid amide hydrolase 1 IC50 = 4050.0 nM 5.39 Inhibition of recombinant C-terminal His-tagged human FAAH expressed in sf21 cel... 26888301

Literature References

PubMed DOI Target Context # Activities
26888301 10.1021/acs.jmedchem.5b01812 Mus musculus 25
26888301 10.1021/acs.jmedchem.5b01812 Heart 25
38241614 10.1021/acs.jmedchem.3c01278 Monoglyceride lipase 20
26888301 10.1021/acs.jmedchem.5b01812 Monoglyceride lipase 7
38241614 10.1021/acs.jmedchem.3c01278 ADMET 6
26888301 10.1021/acs.jmedchem.5b01812 Salmonella typhimurium 4
26888301 10.1021/acs.jmedchem.5b01812 Fatty-acid amide hydrolase 1 3
26888301 10.1021/acs.jmedchem.5b01812 ADMET 2
38241614 10.1021/acs.jmedchem.3c01278 No relevant target 2
38241614 10.1021/acs.jmedchem.3c01278 Unchecked 2
26888301 10.1021/acs.jmedchem.5b01812 Unchecked 2
26888301 10.1021/acs.jmedchem.5b01812 Acyl-protein thioesterase 1/2 1
26888301 10.1021/acs.jmedchem.5b01812 Lysophosphatidylserine lipase ABHD12 1
26888301 10.1021/acs.jmedchem.5b01812 Monoacylglycerol lipase ABHD6 1
26888301 10.1021/acs.jmedchem.5b01812 Cannabinoid receptor 2 1
26888301 10.1021/acs.jmedchem.5b01812 Cannabinoid receptor 1 1
38241614 10.1021/acs.jmedchem.3c01278 Cytochrome P450 2C9 1
38241614 10.1021/acs.jmedchem.3c01278 Cytochrome P450 2D6 1
38241614 10.1021/acs.jmedchem.3c01278 Cytochrome P450 3A4 1

Data from ChEMBL 36 via Core Engine