3-(4-Ethylphenyl)-1-methyl-N-(methylsulfonyl)-1H-indole-6-carboxamide

ID: ALA4536400

PubChem CID: 132051626

Max Phase: Preclinical

Molecular Formula: C19H20N2O3S

Molecular Weight: 356.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1ccc(-c2cn(C)c3cc(C(=O)NS(C)(=O)=O)ccc23)cc1

Standard InChI:  InChI=1S/C19H20N2O3S/c1-4-13-5-7-14(8-6-13)17-12-21(2)18-11-15(9-10-16(17)18)19(22)20-25(3,23)24/h5-12H,4H2,1-3H3,(H,20,22)

Standard InChI Key:  WFHMYKDPZFLJNW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   40.5253   -1.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9421   -2.1131    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.3505   -1.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.2330   -2.5305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6567   -2.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5185   -2.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8094   -2.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5131   -1.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0972   -2.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1129   -3.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8187   -3.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3935   -3.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3853   -2.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6050   -2.3021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1334   -2.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6181   -3.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3448   -1.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3734   -4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5724   -4.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3276   -5.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8807   -5.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6860   -5.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9312   -5.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6352   -6.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8375   -6.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  0
  2  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  2  0
  9 13  1  0
 12 10  1  0
 10 11  2  0
 11  7  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
 14 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536400

   ---

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: 356.45

Molecular Weight (Monoisotopic): 356.1195

AlogP: 3.10

#Rotatable Bonds: 4

Polar Surface Area: 68.17

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.12

CX Basic pKa: ┄

CX LogP: 3.24

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -0.89

References

1. Luo G, Chen L, Easton A, Newton A, Bourin C, Shields E, Mosure K, Soars MG, Knox RJ, Matchett M, Pieschl RL, Post-Munson DJ, Wang S, Herrington J, Graef J, Newberry K, Sivarao DV, Senapati A, Bristow LJ, Meanwell NA, Thompson LA, Dzierba C..  (2019)  Discovery of Indole- and Indazole-acylsulfonamides as Potent and Selective NaV1.7 Inhibitors for the Treatment of Pain.,  62  (2): [PMID:30576602] [10.1021/acs.jmedchem.8b01550]

Source

Source(1):

• Scientific Literature