N-(2-chlorophenylsulfonyl)-2-methoxy-5-((1-methyl-5-nitro-1H-indol-3-yl)methyl)benzamide

ID: ALA5176274

PubChem CID: 168275423

Max Phase: Preclinical

Molecular Formula: C24H20ClN3O6S

Molecular Weight: 513.96

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2cn(C)c3ccc([N+](=O)[O-])cc23)cc1C(=O)NS(=O)(=O)c1ccccc1Cl

Standard InChI:  InChI=1S/C24H20ClN3O6S/c1-27-14-16(18-13-17(28(30)31)8-9-21(18)27)11-15-7-10-22(34-2)19(12-15)24(29)26-35(32,33)23-6-4-3-5-20(23)25/h3-10,12-14H,11H2,1-2H3,(H,26,29)

Standard InChI Key:  IUDWKCBGFBQCEZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.2074   -1.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4928   -1.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -1.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4910   -2.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2074   -2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -2.7942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -1.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5112   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9221   -1.3018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9221   -0.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6367   -1.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144   -0.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    0.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230    0.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067   -0.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957   -0.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -1.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4038    0.1907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    1.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    1.9413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0337    1.5714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    2.3684    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0443    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581    3.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530    3.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6367    3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4257    2.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303    1.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    3.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5326    2.7810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7827   -3.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4168    1.1990    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  2  0
  9  7  1  0
 10  1  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 14 19  1  0
 17 20  1  0
 20 21  1  0
 16 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 26 31  1  0
 25 32  2  0
 25 33  2  0
  7 34  1  0
 31 35  1  0
M  CHG  2  10   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5176274

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 513.96

Molecular Weight (Monoisotopic): 513.0761

AlogP: 4.46

#Rotatable Bonds: 7

Polar Surface Area: 120.54

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.15

CX Basic pKa: ┄

CX LogP: 5.22

CX LogD: 4.28

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.29

Np Likeness Score: -1.33

References

1. Howard KC, Garneau-Tsodikova S..  (2022)  Selective Inhibition of the Periodontal Pathogen Porphyromonas gingivalis by Third-Generation Zafirlukast Derivatives.,  65  (21.0): [PMID:36273428] [10.1021/acs.jmedchem.2c01471]

Source

Source(1):

• Scientific Literature