3-(3-Nitrobenzyl)-5-phenoxy-1,3,4-oxadiazol-2(3H)-one

ID: ALA3613161

PubChem CID: 122188783

Max Phase: Preclinical

Molecular Formula: C15H11N3O5

Molecular Weight: 313.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1oc(Oc2ccccc2)nn1Cc1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C15H11N3O5/c19-15-17(10-11-5-4-6-12(9-11)18(20)21)16-14(23-15)22-13-7-2-1-3-8-13/h1-9H,10H2

Standard InChI Key:  CIWWJOCCTQXUNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -3.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3371   -5.2929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056   -3.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460   -3.4943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9548   -6.4986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624   -7.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -9.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909  -10.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827  -10.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6644   -9.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -8.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 12 13  2  0
 10 14  1  0
 14 15  1  0
 16 17  2  0
 16 18  1  0
  1 16  1  0
 15 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 15  1  0
M  CHG  2  16   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3613161

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 313.27

Molecular Weight (Monoisotopic): 313.0699

AlogP: 2.59

#Rotatable Bonds: 5

Polar Surface Area: 100.40

Molecular Species: ┄

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.53

Np Likeness Score: -1.71

References

1. Patel JZ, van Bruchem J, Laitinen T, Kaczor AA, Navia-Paldanius D, Parkkari T, Savinainen JR, Laitinen JT, Nevalainen TJ..  (2015)  Revisiting 1,3,4-Oxadiazol-2-ones: Utilization in the Development of ABHD6 Inhibitors.,  23  (19): [PMID:26344596] [10.1016/j.bmc.2015.08.030]

2. Hoover, Heather S; Blankman, Jacqueline L; Niessen, Sherry and Cravatt, Benjamin F.  2008-11-15  Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.  [PMID:18657971]

3. Ogasawara, Daisuke and 6 more authors.  2019-02-14  Discovery and Optimization of Selective and in Vivo Active Inhibitors of the Lysophosphatidylserine Lipase α/β-Hydrolase Domain-Containing 12 (ABHD12).  [PMID:30720278]

4. Arena, Chiara and 21 more authors.  2020-12-15  The endocannabinoid system dual-target ligand N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide improves disease severity in a mouse model of multiple sclerosis.  [PMID:33002735]

Source

Source(1):

• Scientific Literature