3-cyclohexyl-N-(cyclopropylsulfonyl)-2-(2-methoxypyrimidin-5-yl)-1-methyl-1H-indole-6-carboxamide

ID: ALA4474646

PubChem CID: 155537052

Max Phase: Preclinical

Molecular Formula: C24H28N4O4S

Molecular Weight: 468.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ncc(-c2c(C3CCCCC3)c3ccc(C(=O)NS(=O)(=O)C4CC4)cc3n2C)cn1

Standard InChI:  InChI=1S/C24H28N4O4S/c1-28-20-12-16(23(29)27-33(30,31)18-9-10-18)8-11-19(20)21(15-6-4-3-5-7-15)22(28)17-13-25-24(32-2)26-14-17/h8,11-15,18H,3-7,9-10H2,1-2H3,(H,27,29)

Standard InChI Key:  NXWYKXBJWDAUGL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.0723   -2.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4890   -2.9877    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.9013   -2.2685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6344   -4.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3508   -4.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3480   -3.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6325   -2.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9195   -4.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9207   -3.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1370   -3.1598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6515   -3.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1351   -4.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8833   -2.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.8156   -6.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.0610   -2.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7770   -3.4036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0578   -2.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2060   -3.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6232   -4.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0330   -3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8297   -3.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4188   -3.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5946   -3.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1802   -3.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5961   -4.5409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4190   -4.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3552   -3.8233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9427   -3.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
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  5  6  1  0
  6  7  2  0
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  9 10  1  0
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 18 19  1  0
 12 14  1  0
  6 20  1  0
 20 21  1  0
 20 22  2  0
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  2 23  1  0
 24 23  1  0
 25 24  1  0
 23 25  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 11 26  1  0
 29 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474646

   ---

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: 468.58

Molecular Weight (Monoisotopic): 468.1831

AlogP: 3.91

#Rotatable Bonds: 6

Polar Surface Area: 103.18

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: 1.32

CX LogP: 3.68

CX LogD: 2.74

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.59

Np Likeness Score: -0.70

References

1. Wu YJ, Venables B, Guernon J, Chen J, Sit SY, Rajamani R, Knox RJ, Matchett M, Pieschl RL, Herrington J, Bristow LJ, Meanwell NA, Thompson LA, Dzierba C..  (2019)  Discovery of new indole-based acylsulfonamide Na_v1.7 inhibitors.,  29  (4): [PMID:30638874] [10.1016/j.bmcl.2018.12.013]

Source

Source(1):

• Scientific Literature