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

ID: ALA4778192

PubChem CID: 162644334

Max Phase: Preclinical

Molecular Formula: C19H23N3O3

Molecular Weight: 341.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]cc(CCc3nn(CC4CCCC4)c(=O)o3)c2c1

Standard InChI:  InChI=1S/C19H23N3O3/c1-24-15-7-8-17-16(10-15)14(11-20-17)6-9-18-21-22(19(23)25-18)12-13-4-2-3-5-13/h7-8,10-11,13,20H,2-6,9,12H2,1H3

Standard InChI Key:  WYHAXZNIVSDTLE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.8017  -15.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8006  -16.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5086  -17.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5069  -15.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2155  -15.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2157  -16.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9944  -17.0566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4754  -16.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9940  -15.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0939  -15.5804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3863  -15.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2462  -14.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0455  -14.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2978  -14.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0719  -13.7561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0716  -12.9389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2943  -12.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8143  -13.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0414  -11.9095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7326  -12.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4792  -12.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6493  -13.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4620  -13.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7942  -12.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1866  -12.3804    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
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778192

   ---

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: 341.41

Molecular Weight (Monoisotopic): 341.1739

AlogP: 3.30

#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: 3.92

CX LogD: 3.92

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -0.76

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