(S)-5-bromo-3',4'-bis(3-chlorophenyl)-4'H-spiro[indoline-3,5'-[1,2,4]oxadiazol]-2-one

ID: ALA3797570

PubChem CID: 127046731

Max Phase: Preclinical

Molecular Formula: C21H12BrCl2N3O2

Molecular Weight: 489.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccc(Br)cc2[C@]12ON=C(c1cccc(Cl)c1)N2c1cccc(Cl)c1

Standard InChI:  InChI=1S/C21H12BrCl2N3O2/c22-13-7-8-18-17(10-13)21(20(28)25-18)27(16-6-2-5-15(24)11-16)19(26-29-21)12-3-1-4-14(23)9-12/h1-11H,(H,25,28)/t21-/m0/s1

Standard InChI Key:  YGWNEVQVVZQISY-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   -0.5725   -1.9258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2776   -0.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5725    0.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5977    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5977   -1.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791   -2.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -1.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    1.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665    2.8107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2082    2.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    1.3533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776   -0.7073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988    4.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927    3.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847    5.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775    6.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783    6.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3863    5.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -0.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9329   -0.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9829    0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5804    1.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277    1.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6282    0.6496    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.2549   -2.1011    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5841    5.2037    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  1  9  1  0
  4  9  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  3 10  1  0
  3 13  1  0
  2 14  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 12 15  1  0
 13 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  6 27  1  0
 23 28  1  0
 17 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3797570

   ---

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: 489.16

Molecular Weight (Monoisotopic): 486.9490

AlogP: 5.76

#Rotatable Bonds: 2

Polar Surface Area: 53.93

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.36

CX Basic pKa: ┄

CX LogP: 6.96

CX LogD: 6.96

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -0.73

References

1. Ribeiro CJA, Amaral JD, Rodrigues CMP, Moreira R, Santos MMM.  (2016)  Spirooxadiazoline oxindoles with promising in vitro antitumor activities,  7  (3): [10.1039/C5MD00450K]

Source

Source(1):

• Scientific Literature