2-methoxy-5-[(1-methylindol-3-yl)methyl]-N-(4-nitrophenyl)sulfonyl-benzamide

ID: ALA4752352

PubChem CID: 162652455

Max Phase: Preclinical

Molecular Formula: C24H21N3O6S

Molecular Weight: 479.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2cn(C)c3ccccc23)cc1C(=O)NS(=O)(=O)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C24H21N3O6S/c1-26-15-17(20-5-3-4-6-22(20)26)13-16-7-12-23(33-2)21(14-16)24(28)25-34(31,32)19-10-8-18(9-11-19)27(29)30/h3-12,14-15H,13H2,1-2H3,(H,25,28)

Standard InChI Key:  HLUARFLHDDIWJD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   18.3662  -24.9120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1586  -25.1266    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9482  -24.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5730  -29.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5719  -29.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2799  -30.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2781  -28.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9868  -29.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9870  -29.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7700  -30.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2537  -29.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7696  -28.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0219  -27.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8211  -27.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3651  -28.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1637  -28.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4167  -27.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8649  -26.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0684  -27.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2158  -27.2936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7636  -27.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1145  -26.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9131  -25.9052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5653  -25.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9613  -24.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5087  -25.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3108  -25.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5634  -24.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0078  -24.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2078  -24.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0227  -30.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3641  -24.4380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9131  -25.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6138  -23.6599    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  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 23  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 10 31  1  0
 32 33  1  0
 32 34  2  0
 28 32  1  0
M  CHG  2  32   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4752352

   ---

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: 479.51

Molecular Weight (Monoisotopic): 479.1151

AlogP: 3.80

#Rotatable Bonds: 7

Polar Surface Area: 120.54

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.18

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 3.68

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -1.06

References

1. Howard KC,Gonzalez OA,Garneau-Tsodikova S.  (2020)  Second Generation of Zafirlukast Derivatives with Improved Activity against the Oral Pathogen Porphyromonas gingivalis.,  11  (10): [PMID:33062172] [10.1021/acsmedchemlett.9b00614]

Source

Source(1):

• Scientific Literature