compound 6 [PMID: 25874594]

Ligand id: 9178

Name: compound 6 [PMID: 25874594]

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 67.43
Molecular weight 268.18
XLogP 3.74
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
4-cyclohexylbutyl N-[(3S)-2-oxoazetidin-3-yl]carbamate
Comments
Compound 6 is from a series of β-lactam derivatives that are potent, selective, and systemically active inhibitors of intracellular N-Acylethanolamine acid amidase (NAAA) by covalently binding the enzyme's catalytic cysteine. It exhibits anti-inflammatory effects in both mouse models and human macrophages [2]. In the corresponding patent [1] the structure seems to be example 5, but a higher potency of 750 nM IC50 is recorded compared to 3500 nM in the paper. There is a patchy SAR table for 106 structures on page 104 of the WO2014144836 PDF. The R isomer of this structure PubChem CID 86282216 is reported to be less active.
Database Links
GtoPdb PubChem SID 315661261
PubChem CID 78319072
Search Google for chemical match using the InChIKey FNLUJRBWJBUJTC-LBPRGKRZSA-N
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Search UniChem for chemicals with the same backbone FNLUJRBWJBUJTC