5-[(E)-2-(5-Methoxy-1H-indol-3-yl)ethenyl]-1,3,4-oxadiazol-2(3H)-one

ID: ALA4783536

PubChem CID: 162666068

Max Phase: Preclinical

Molecular Formula: C13H11N3O3

Molecular Weight: 257.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]cc(/C=C/c3n[nH]c(=O)o3)c2c1

Standard InChI:  InChI=1S/C13H11N3O3/c1-18-9-3-4-11-10(6-9)8(7-14-11)2-5-12-15-16-13(17)19-12/h2-7,14H,1H3,(H,16,17)/b5-2+

Standard InChI Key:  MBWWTUVCPDXVML-GORDUTHDSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   16.3383  -25.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3371  -26.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0452  -27.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0434  -25.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7520  -25.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7523  -26.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5309  -26.9867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0120  -26.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5305  -25.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6305  -25.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9229  -25.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7828  -24.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5820  -24.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8343  -23.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6084  -23.6862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6081  -22.8690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8308  -22.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3508  -23.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5779  -21.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 17 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4783536

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 257.25

Molecular Weight (Monoisotopic): 257.0800

AlogP: 2.02

#Rotatable Bonds: 3

Polar Surface Area: 83.91

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.27

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 1.80

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.75

Np Likeness Score: -0.26

References

1. Herrera-Arozamena C,Estrada-Valencia M,Pérez C,Lagartera L,Morales-García JA,Pérez-Castillo A,Franco-Gonzalez JF,Michalska P,Duarte P,León R,López MG,Mills A,Gago F,García-Yagüe ÁJ,Fernández-Ginés R,Cuadrado A,Rodríguez-Franco MI.  (2020)  Tuning melatonin receptor subtype selectivity in oxadiazolone-based analogues: Discovery of QR2 ligands and NRF2 activators with neurogenic properties.,  190  [PMID:32018096] [10.1016/j.ejmech.2020.112090]

Source

Source(1):

• Scientific Literature