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

ID: ALA4520640

PubChem CID: 155542498

Max Phase: Preclinical

Molecular Formula: C18H15N3O6S

Molecular Weight: 401.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C2(CCCc3ccccc32)N1S(=O)(=O)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C18H15N3O6S/c22-16-18(11-3-5-12-4-1-2-6-15(12)18)20(17(23)19-16)28(26,27)14-9-7-13(8-10-14)21(24)25/h1-2,4,6-10H,3,5,11H2,(H,19,22,23)

Standard InChI Key:  VUXUVHNPNINYJZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    6.3338  -19.1380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043  -18.7698    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6502  -19.5857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5342  -17.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170  -17.9975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4644  -18.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1255  -19.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7866  -18.7747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0044  -19.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0033  -20.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7113  -20.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7095  -19.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181  -19.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4170  -20.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232  -20.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351  -20.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8362  -19.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872  -19.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0146  -17.3365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0107  -18.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8260  -18.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2319  -17.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8205  -16.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991  -16.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5970  -17.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2255  -15.9366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0427  -15.9325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8134  -15.2310    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  CHG  2  26   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4520640

   ---

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: 401.40

Molecular Weight (Monoisotopic): 401.0682

AlogP: 2.07

#Rotatable Bonds: 3

Polar Surface Area: 126.69

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.37

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -0.77

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