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
Database Links
GtoPdb PubChem SID 315661261
PubChem CID 78319072
Search Google for chemical match using the InChIKey FNLUJRBWJBUJTC-LBPRGKRZSA-N
Search Google for chemicals with the same backbone FNLUJRBWJBUJTC
Search UniChem for chemical match using the InChIKey FNLUJRBWJBUJTC-LBPRGKRZSA-N
Search UniChem for chemicals with the same backbone FNLUJRBWJBUJTC
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.