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

ID: ALA4794019

PubChem CID: 162672844

Max Phase: Preclinical

Molecular Formula: C16H19N3O3

Molecular Weight: 301.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCn1nc(CCc2c[nH]c3ccc(OC)cc23)oc1=O

Standard InChI:  InChI=1S/C16H19N3O3/c1-3-8-19-16(20)22-15(18-19)7-4-11-10-17-14-6-5-12(21-2)9-13(11)14/h5-6,9-10,17H,3-4,7-8H2,1-2H3

Standard InChI Key:  WBTKSZBUMSSJPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   15.3643   -5.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3631   -6.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0712   -6.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0694   -5.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7780   -5.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7783   -6.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5569   -6.6478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0379   -5.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5565   -5.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6564   -5.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9488   -5.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8087   -4.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6080   -4.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8603   -3.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6344   -3.3472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6341   -2.5300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8568   -2.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3768   -2.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6039   -1.5006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2951   -2.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0417   -2.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7027   -1.9010    0.0000 C   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  1  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
 16 20  1  0
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794019

   ---

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: 301.35

Molecular Weight (Monoisotopic): 301.1426

AlogP: 2.52

#Rotatable Bonds: 6

Polar Surface Area: 73.05

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.13

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: -0.96

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