3-(5-Chloro-6-isobutoxypyridin-3-yl)-5-fluoro-1-methyl-N-(methylsulfonyl)-1H-indole-6-carboxamide

ID: ALA4475017

PubChem CID: 132020584

Max Phase: Preclinical

Molecular Formula: C20H21ClFN3O4S

Molecular Weight: 453.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)COc1ncc(-c2cn(C)c3cc(C(=O)NS(C)(=O)=O)c(F)cc23)cc1Cl

Standard InChI:  InChI=1S/C20H21ClFN3O4S/c1-11(2)10-29-20-16(21)5-12(8-23-20)15-9-25(3)18-7-14(17(22)6-13(15)18)19(26)24-30(4,27)28/h5-9,11H,10H2,1-4H3,(H,24,26)

Standard InChI Key:  FVUIYPLOVITXKN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.7442  -10.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1610  -11.7048    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5694  -10.9883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4519  -12.1222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8756  -12.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7374  -11.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0283  -12.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7321  -10.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3161  -11.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3319  -13.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0376  -12.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6124  -12.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6043  -12.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8239  -11.8937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3523  -12.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8371  -13.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5637  -11.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5923  -14.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7913  -14.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5465  -14.9598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0996  -15.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9049  -15.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1501  -14.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8541  -16.3461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0564  -16.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8109  -17.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -17.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3632  -17.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4585  -15.9863    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.7492  -13.3498    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
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 12 13  2  0
 13 14  1  0
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 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
 25 26  1  0
 26 27  1  0
 26 28  1  0
 22 29  1  0
 11 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475017

   ---

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: 453.92

Molecular Weight (Monoisotopic): 453.0925

AlogP: 3.76

#Rotatable Bonds: 6

Polar Surface Area: 90.29

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.00

CX Basic pKa: 0.72

CX LogP: 3.49

CX LogD: 2.55

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.61

Np Likeness Score: -1.23

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