ARN726   

GtoPdb Ligand ID: 9178

Synonyms: ARN-726 | compound 6 [PMID: 25874594]
Compound class: Synthetic organic
Comment: ARN726 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. 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.
2D Structure
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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
SMILES / InChI / InChIKey
Canonical SMILES O=C(NC1CNC1=O)OCCCCC1CCCCC1
Isomeric SMILES O=C(N[C@H]1CNC1=O)OCCCCC1CCCCC1
InChI InChI=1S/C14H24N2O3/c17-13-12(10-15-13)16-14(18)19-9-5-4-8-11-6-2-1-3-7-11/h11-12H,1-10H2,(H,15,17)(H,16,18)/t12-/m0/s1
InChI Key FNLUJRBWJBUJTC-LBPRGKRZSA-N
Classification
Compound class Synthetic organic
IUPAC Name
4-cyclohexylbutyl N-[(3S)-2-oxoazetidin-3-yl]carbamate
Synonyms
ARN-726 | compound 6 [PMID: 25874594]
Database Links
GtoPdb PubChem SID 315661261
PubChem CID 78319072
Search Google for chemical match using the InChIKey FNLUJRBWJBUJTC-LBPRGKRZSA-N
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Tocris
ARN 726
Cat. No. 5861