(R)-ARN2508   

GtoPdb Ligand ID: 9000

Synonyms: compound (-)-10r [PMID: 26774927] | example 19 [WO2014023643]
Compound class: Synthetic organic
Comment: (R)-ARN2508 is an experimental inhibitor of fatty acid amide hydrolase (FAAH) [2], claimed in patent WO2014023643 [1]. The compound series developed by Migliore et al. (2015) [2] is based on a hybrid scaffold combining structural motifs of the FAAH inhibitor URB597 and the COX inhibitor flurbiprofen. The (S) enantiomer ((S)-ARN2508) inhibits both FAAH and COX enzyme activities, whereas this (R) enantiomer only inhibits FAAH.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 75.63
Molecular weight 387.18
XLogP 5.68
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCNC(=O)Oc1cccc(c1)c1ccc(cc1F)C(C(=O)O)C
Isomeric SMILES CCCCCCNC(=O)Oc1cccc(c1)c1ccc(cc1F)[C@H](C(=O)O)C
InChI InChI=1S/C22H26FNO4/c1-3-4-5-6-12-24-22(27)28-18-9-7-8-17(13-18)19-11-10-16(14-20(19)23)15(2)21(25)26/h7-11,13-15H,3-6,12H2,1-2H3,(H,24,27)(H,25,26)/t15-/m1/s1
InChI Key USQOVYLRWBOSQC-OAHLLOKOSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(2R)-2-(3-fluoro-4-{3-[(hexylcarbamoyl)oxy]phenyl}phenyl)propanoic acid
Synonyms
compound (-)-10r [PMID: 26774927] | example 19 [WO2014023643]
Database Links
GtoPdb PubChem SID 310264778
PubChem CID 117072557
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