2-(2-Methyl-1,4-dihydroindeno[1,2-b]pyrrol-3-yl)-5-phenyl-1,3,4-oxadiazole

ID: ALA3975545

PubChem CID: 137247637

Max Phase: Preclinical

Molecular Formula: C20H15N3O

Molecular Weight: 313.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2c(c1-c1nnc(-c3ccccc3)o1)Cc1ccccc1-2

Standard InChI:  InChI=1S/C20H15N3O/c1-12-17(16-11-14-9-5-6-10-15(14)18(16)21-12)20-23-22-19(24-20)13-7-3-2-4-8-13/h2-10,21H,11H2,1H3

Standard InChI Key:  ASVQGQLIXGMQDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   10.1488  -14.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7998  -14.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5114  -13.4191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7116  -13.4383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834  -14.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7213  -14.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0309  -14.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3758  -14.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6574  -15.3128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932  -15.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7145  -14.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9159  -14.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3495  -13.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5777  -12.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3763  -12.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9427  -13.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7425  -13.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5887  -14.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9998  -15.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3031  -13.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5887  -15.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3031  -15.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0176  -15.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0176  -14.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  5  6  1  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
  9 10  1  0
  6 10  2  0
  8 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 16 11  1  0
 17 16  1  0
  7 17  1  0
  2 18  1  0
 10 19  1  0
 20 18  2  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3975545

   ---

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: 313.36

Molecular Weight (Monoisotopic): 313.1215

AlogP: 4.61

#Rotatable Bonds: 2

Polar Surface Area: 54.71

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.02

CX Basic pKa: ┄

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: -0.67

References

1. Nieddu V, Pinna G, Marchesi I, Sanna L, Asproni B, Pinna GA, Bagella L, Murineddu G..  (2016)  Synthesis and Antineoplastic Evaluation of Novel Unsymmetrical 1,3,4-Oxadiazoles.,  59  (23): [PMID:27801583] [10.1021/acs.jmedchem.6b00468]

2. Zoroddu S, Corona P, Sanna L, Borghi F, Bordoni V, Asproni B, Pinna GA, Bagella L, Murineddu G..  (2022)  Novel 1,3,4-oxadiazole chalcogen analogues: Synthesis and cytotoxic activity.,  238  [PMID:35576700] [10.1016/j.ejmech.2022.114440]

Source

Source(1):

• Scientific Literature