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

ID: ALA4783454

PubChem CID: 162665431

Max Phase: Preclinical

Molecular Formula: C16H13N3O3

Molecular Weight: 295.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#CCn1nc(/C=C/c2c[nH]c3ccc(OC)cc23)oc1=O

Standard InChI:  InChI=1S/C16H13N3O3/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/h1,4-7,9-10,17H,8H2,2H3/b7-4+

Standard InChI Key:  FMLVPVUAWFQXKW-QPJJXVBHSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   28.2164  -26.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2153  -27.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9233  -27.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9216  -26.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6302  -26.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6304  -27.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4091  -27.5109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8901  -26.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4087  -26.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5086  -26.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8010  -26.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6609  -25.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4602  -25.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7125  -24.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4866  -24.2103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4863  -23.3931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7090  -23.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2290  -23.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4561  -22.3638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1473  -22.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8939  -23.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6395  -23.5762    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  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
 16 20  1  0
 20 21  1  0
 21 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4783454

   ---

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: 295.30

Molecular Weight (Monoisotopic): 295.0957

AlogP: 2.13

#Rotatable Bonds: 4

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: 2.56

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: -0.66

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