3-(4-(Difluoromethyl)phenyl)-5-fluoro-1-methyl-N-(methylsulfonyl)-1H-indole-6-carboxamide

ID: ALA4475206

PubChem CID: 132020419

Max Phase: Preclinical

Molecular Formula: C18H15F3N2O3S

Molecular Weight: 396.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2ccc(C(F)F)cc2)c2cc(F)c(C(=O)NS(C)(=O)=O)cc21

Standard InChI:  InChI=1S/C18H15F3N2O3S/c1-23-9-14(10-3-5-11(6-4-10)17(20)21)12-7-15(19)13(8-16(12)23)18(24)22-27(2,25)26/h3-9,17H,1-2H3,(H,22,24)

Standard InChI Key:  XLKUKOXKOULLDW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.9887   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4055   -1.9274    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.8139   -1.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6964   -2.3448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1201   -2.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9819   -1.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2728   -2.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9765   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5606   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5764   -3.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2821   -3.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8569   -3.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8488   -2.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0684   -2.1163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5968   -2.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0816   -3.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8082   -1.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8368   -4.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0358   -4.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7910   -5.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3441   -5.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1494   -5.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3946   -4.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0986   -6.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3009   -6.7458    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.6509   -7.1710    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.9937   -3.5724    0.0000 F   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
 24 26  1  0
 11 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475206

   ---

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: 396.39

Molecular Weight (Monoisotopic): 396.0755

AlogP: 3.61

#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: 4.00

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 1.87

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.99

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