3,4-Dihydro-1'-(4-acetylphenylsulfonyl)spiro[imidazoline-5',1(2H)-naphthalene]-2',4'-dione

ID: ALA4539238

PubChem CID: 155550245

Max Phase: Preclinical

Molecular Formula: C20H18N2O5S

Molecular Weight: 398.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc(S(=O)(=O)N2C(=O)NC(=O)C23CCCc2ccccc23)cc1

Standard InChI:  InChI=1S/C20H18N2O5S/c1-13(23)14-8-10-16(11-9-14)28(26,27)22-19(25)21-18(24)20(22)12-4-6-15-5-2-3-7-17(15)20/h2-3,5,7-11H,4,6,12H2,1H3,(H,21,24,25)

Standard InChI Key:  JAVDYLNBJZIQBH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   20.1765  -19.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4470  -18.9060    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.4929  -19.7219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3769  -18.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5597  -18.1337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3071  -18.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9682  -19.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6293  -18.9109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8471  -19.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8460  -20.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5540  -21.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5523  -19.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2609  -19.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2597  -20.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9659  -21.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6778  -20.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6789  -19.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5299  -19.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8574  -17.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8535  -18.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6687  -18.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0746  -17.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6633  -16.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8419  -16.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4397  -17.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0683  -16.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8854  -16.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6561  -15.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 13  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  7  1  0
  6 18  2  0
  4 19  2  0
  8  2  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539238

   ---

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: 398.44

Molecular Weight (Monoisotopic): 398.0936

AlogP: 2.36

#Rotatable Bonds: 3

Polar Surface Area: 100.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.37

CX Basic pKa: ┄

CX LogP: 2.65

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -0.48

References

1. Iqbal Z, Morahan G, Arooj M, Sobolev AN, Hameed S..  (2019)  Synthesis of new arylsulfonylspiroimidazolidine-2',4'-diones and study of their effect on stimulation of insulin release from MIN6 cell line, inhibition of human aldose reductase, sorbitol accumulations in various tissues and oxidative stress.,  168  [PMID:30818176] [10.1016/j.ejmech.2019.02.036]

Source

Source(1):

• Scientific Literature