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Compound Detail

CHEMBL177577

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O=C(CCCCCCc1ccccc1)c1ncc(-c2ccccn2)o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL177577
Phase Preclinical
Structure Type MOL
InChI Key ILOIOIGZFHGSMS-UHFFFAOYSA-N
5
Targets
46
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

334.4
MW (Da)
5.11
ALogP
4
HBA
0
HBD
56.0
PSA (Ų)
0.40
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C21H22N2O2
MW 334.42
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.55

Activity Summary

Ki 25 meas. best 8.52
IC50 21 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Fatty-acid amide hydrolase 1
CHEMBL2243
 IC50 9.4 7.8609 0.4 11
Fatty-acid amide hydrolase 1
CHEMBL3229
 IC50 8.7 7.715 2.0 4
Fatty-acid amide hydrolase 1
CHEMBL3229
 Ki 8.52 8.352 3.0 15
Fatty-acid amide hydrolase 1
CHEMBL2243
 Ki 8.33 8.21 4.7 7
Fatty-acid amide hydrolase 1
CHEMBL3455
 Ki 8.33 8.33 4.7 2
Fatty-acid amide hydrolase 2
CHEMBL1628475
 IC50 7.87 7.87 13.4 1
Liver carboxylesterase 1
CHEMBL2265
 IC50 6.22 6.22 600.0 5

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.03333 hr Rattus norvegicus
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Fatty-acid amide hydrolase 1 IC50 = 0.4 nM 9.4 Inhibition of MBP-fused human recombinant FAAH with truncated N-terminal transme... 27130358
Fatty-acid amide hydrolase 1 IC50 = 2.0 nM 8.7 Inhibitory concentration against Fatty-acid amide hydrolase 15771430
Fatty-acid amide hydrolase 1 IC50 = 2.0 nM 8.7 Inhibition of rat recombinant FAAH expressed in Escherichia coli by [14C]oleamid... 17279740
Fatty-acid amide hydrolase 1 IC50 = 2.0 nM 8.7 Inhibition of rat recombinant FAAH expressed in Escherichia coli 18247553
Fatty-acid amide hydrolase 1 IC50 = 2.0 nM 8.7 Inhibition of rat FAAH 18639454
Fatty-acid amide hydrolase 1 Ki = 3.0 nM 8.52 Time-dependent inhibition of recombinant rat FAAH expressed in Escherichia coli ... 24456116
Fatty-acid amide hydrolase 1 Ki = 3.8 nM 8.42 Time-dependent inhibition of recombinant rat FAAH expressed in Escherichia coli ... 24456116
Fatty-acid amide hydrolase 1 Ki = 4.2 nM 8.38 Time-dependent inhibition of recombinant rat FAAH expressed in Escherichia coli ... 24456116
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of rat recombinant FAAH expressed in Escherichia coli 19924997
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of rat recombinant FAAH expressed in Escherichia coli 22196515
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of rat FAAH preincubated for 20 mins 18693015
Fatty-acid amide hydrolase 1 IC50 = 4.7 nM 8.33 Reversible inhibition of human recombinant FAAH assessed as hydrolysis of [3H]-A... 21899370
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibitory constant determined against recombinant Fatty-acid amide hydrolase fr... 15771430
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibitor affinity towards enzymes of class serine hydrolase was determined usin... 15713400
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Binding affinity against purified rat Fatty-acid amide hydrolase (FAAH) expresse... 15582420
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of rat recombinant FAAH expressed in Escherichia coli by [14C]oleamid... 17279740
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of rat recombinant FAAH expressed in Escherichia coli 17559203
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of rat FAAH 18053726
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of FAAH 18247553
Fatty-acid amide hydrolase 1 Ki = 4.7 nM 8.33 Inhibition of rat cortex FAAH by [3H]anandamide carbon filtration assay 19072118

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5303304 Fibroblast 14
21428410 10.1021/jm101597x Mus musculus 8
- 10.6019/CHEMBL5303304 HEK-293T 7
24456116 10.1021/jm401820q Mus musculus 6
24456116 10.1021/jm401820q Fatty-acid amide hydrolase 1 5
23891163 10.1016/j.bmc.2013.06.034 Fatty-acid amide hydrolase 1 4
19515560 10.1016/j.bmcl.2009.05.097 Fatty-acid amide hydrolase 1 4
- 10.6019/CHEMBL5303304 U2OS 4
18053726 10.1016/j.bmc.2007.11.015 Unchecked 4
18693015 10.1016/j.bmcl.2008.07.081 Fatty-acid amide hydrolase 1 3
15771430 10.1021/jm049614v Fatty-acid amide hydrolase 1 3
18630870 10.1021/jm800136b Fatty-acid amide hydrolase 1 3
30503633 10.1016/j.bmcl.2018.11.048 Fatty-acid amide hydrolase 1 3
17559203 10.1021/jm061414r Unchecked 2
18053726 10.1016/j.bmc.2007.11.015 Fatty-acid amide hydrolase 1 2
18639454 10.1016/j.bmcl.2008.06.084 Fatty-acid amide hydrolase 1 2
22779702 10.1021/jm300689c Fatty-acid amide hydrolase 1 2
17279740 10.1021/jm0611509 Unchecked 2
15713400 10.1016/j.bmcl.2004.12.085 Fatty-acid amide hydrolase 1 2
18247553 10.1021/jm701210y Unchecked 2

Data from ChEMBL 36 via Core Engine